Finding Our Way

Peter and Jesse are joined by organization designer Clay Parker Jones, author of Hidden Patterns: A Playbook for More Human Workplaces, who has led organization design work at Airbnb, Undercurrent, R/GA, and August. The conversation covers why roles persist, the importance of indexing on trust over role clarity, the difference between psychological and structural safety, organizational rule of law, and why demonstrating better teams beats trying to convince skeptics.
Clay Parker Jones: https://cpj.fyi, Hidden Patterns book

Jesse James Garrett: https://jessejamesgarrett.com/

Peter Merholz: https://petermerholz.com/

Jesse: I’m Jesse James Garrett.

Peter: And I’m Peter Merholz.

Jesse: And we’re

Peter: finding our way. Navigating the opportunities- And challenges- Of design and design leadership.

Jesse: On today’s show we’re joined by organization designer Clay Parker Jones And author of the book Hidden Patterns: A Playbook for More Human Workplaces. We’ll get into the untapped value that is unlocked through organization design, why teams might be better off indexing on trust rather than clarity, and strategies for overcoming organizational resistance to change.

Peter: Clay, thank you for joining us.

Clay: Happy to be here.

Peter: You’re probably a little less standard of a guest- … on Finding Our Way, in that you’re not a UX design type. So for our audience who might not be familiar with you, how do you introduce yourself?

Clay: Well, firstly, when I was young, I did want to become a UX designer.

And I very much looked up to the both of you and the work that Adaptive Path did. So not being a good enough designer, I think, led me to be an organization designer.

Peter: Which is something I, I now share myself.

Clay: Hey, life brings us many changes. Okay. So how do I introduce myself? I’m an organization designer.

I am now an author. I’m now also a dad. I live here in Brooklyn, New York, with my wife and son and cat, Ian. I’m a former bicycle mechanic.

Peter: Organization designer is one of those roles that I think people have heard but don’t really know what they do. Yes. What would you say an organization designer does?

Clay: Like, the formal answer or the way that if I was trying to explain it to someone who’s going to be paying me would be something around the structuring of units to help people achieve a goal, or the reforming of an organization in its various constituent parts in order to deliver some improved outcome for stakeholders.

That’s, like, a real nerdy example or a real nerdy way to talk about it. I think the way that I think about it personally is waking up with a mission of the people that you’re working with being able to get more and better work done today than they did yesterday, and continuing to do that over and over again.

The idea of design is useful because it introduces, like, a category boundary. But I, I think so much of this work is actually just in… It’s in the margins. It’s in the meeting that goes well or goes poorly. It’s in the role that is well-described or poorly described. It’s in the team that knows that the other teams around them are gonna keep doing the things that they said that they were going to do and not always, or maybe increasingly so, not infringe on their territory or step on their toes.

It’s in people feeling really excited about their work. And whatever mechanisms we might use in order to get there, it might be a PowerPoint deck containing a org chart. It might be a piece of software. It might be a prompt that somebody gets or a prompt that somebody gives to a intelligence. It’s all kinds of things.

But it gets pretty narrowed into this idea of, oh, we’re making a deck for a senior leader that follows, like, this diagnose, design, deliver kind of pattern. And I think that’s increasingly unuseful or even unhelpful in the way that we define the field.

Jesse: What are some of the other tools that you’d like to see come into play in how organization design is done?

Clay: I think it’s more about the distribution of the knobs or the levers or, like, the palettes that we might paint with to more and more people. And I don’t mean that through terms or ideas like self-management necessarily. That may be something that happens, but mostly just that more teams are able to have more of an impact on the way that they are themselves designed, the way that they have agreed with each other that they’re going to work, and that more people are doing it more frequently at a higher and higher level over time.

So it’s less about, like, the tooling exactly, and more about, like, more people adopting whatever tooling it might be.

Peter: Mm-hmm. Correct me if I’m wrong, but org design, at least the way you practice it, is more defined by its outcomes of an improved org. Whereas while that had been the goal of UX design when Jesse and I were doing this 20-some years ago, UX design, over the last decade-plus, has been defined by its artifacts and its process and what it creates, less by its impact.

And I’m wondering, well, one, an opportunity, I think, right now for UX design is to be less defined by its tools and process and artifacts, and more by its impact. And I guess with org design, I’m wondering, have you seen it defined by its stuff, or has it been able to stay a bit truer to an orientation on impact?

Clay: I think that there’s, like, roughly two portions of the field.

There’s this kind of like structuralist portion that gets paid for doing organization design, and that is seen by stakeholders as org designers. And those people are typically at one of the big consultancies, less so like an August, less so like The Ready, and more so like McKinsey or Kates Kesler, now part of Accenture.

And they’re defined by outcomes, but they’re also very much defined by the actual artifact. There is a perceptible feel to one of their documents, that where even if it has the company logo at the bottom, you know who wrote this thing. And the outcomes are far, so far in the distance. They’re gonna come to us five, 10 years from now when we finally bring together all these operating units that have been operating on their own, with their own intention and with their own structure, and now we’re bringing them together and we’re gonna achieve some efficiencies. That’s gonna happen way far in the distance, and the outcome is not really even part of the conversation. It’s the output. It’s the thing that we all agree is, like, gonna be the effective transfer of power.

And then there’s, like, this, I refer to as, like, a mutualist side of the practice, which is more about helping people define their work together and giving them the tools and the technologies and the language to actually be able to do that.

And that is almost entirely outcome driven, and it gets paid a lot more reasonably than do, like, the structuralist org designers, right?

And I think there’s a little bit of the mission kind of getting in the way there to a certain extent, if all we’re trying to do is get paid.

But, at very least, there’s like these two sides. One is called org design, one is usually called, like, culture work or ways of working work, but it is org design. It’s changing the way that the organization is structured, intentionally, for good, usually, or that’s the intent or the hope.

And then the other side is we’re trying to, we’re trying to hack it, and sometimes we get called in, sometimes we get brought in after the big consultancies get called in, and that is entirely always going to be sold.

We always did at August, sell it in terms of the things that are, that our clients are going to be able to observe in the organization, not something that they’re gonna be able to hold onto, which maybe is a bad consulting strategy.

Peter: Mm-hmm. Mm-hmm.

Jesse: Some would say.

Clay: Sure.

Peter: The impetus to have you join us on our podcast was something that you published in February called The End of Role Clarity, which I ended up responding to in a newsletter article of my own.

But before we get into a dialogue, I think it would be good, for those who haven’t had a chance to read it, if you could just share the thesis. It’s a long enough article, so I’m sure you’re gonna have to elide some details, but what is your high order thesis when you were writing The End of Role Clarity?

Clay: Yeah. In large organizations, so much of the conversation ends up being about, “Oh, well, we don’t have role clarity.” And it’s something people say when they are trying not exactly to avoid taking action, but it often allows people to do that. We’re not going to take advantage of this opportunity because we don’t have role clarity, because I’m not sure if that person over there is supposed to be doing that thing that they’re doing that I think I should be doing, and it’s getting in the way of us being able to make a good decision.

And I wanted to offer with that piece this alternative view, which I think is more and more plausible or possible with, or maybe even required or will be forced upon us by the introduction of new technologies that allow more people to do things that they didn’t know how to do before. Whether or not they know if the output is good or not is sort of beside the point, but it is going to allow more people to be designers, be musicians. It’s going to allow people to do more things.

So that means that individual roles as we have defined them today, like an engineer or a product manager or a designer, become less useful or interesting distinctions between roles because teams are able to just say, “All right, yeah, I can kind of be a software engineer if I’m a designer with an interest in artificial intelligence and figuring out, like wading through the process of like getting Terminal working for me and being able to work in the command line. Oh, I can actually be useful, and I can make a prototype with the design sense that I have.”

Or if I’m a product manager, I can actually do some of the design work using some tokens that I’m pulling from a library that’s been well architected by actual designers. And that means that the more useful thing to be focused on is less, like, are they perfectly defined, and do they have no overlap between the two individual roles, or do they know how to work very well as a team because they have a clear team purpose, they have a clear sense of our focus areas, they have a clear understanding of how we’re going to be measured. They know where we’re going to work, they know and they’ve made an agreement together about how they intend to work.

That’s much more useful than this idea of role clarity, which feels antiquated and stuck in this idea of the org chart being defined by the employment agreement, which I think, again, is going to be less and less interesting over time for the people who, I don’t want to say the people with the most talent exactly, but the people who are like really leaning into trying new tools and building with AI.

Like they’re gonna want to be doing more, and that’ll change the way that we think about the team, and in ways that are in the near term probably not always so good and feel a little bit like, “Ooh, am I losing some of my identity in this?”

So that was the piece. I think I’ve stepped away from the computer for a while to raise my now 12-week-old son. So hopefully that is mostly what I tried to say. And I know, Peter, you disagreed with me to a certain extent, and you emailed me right after I posted it. “We need to talk about this.” Which I knew then that I had done something good for the world in introducing something that people may find disagreeable, if not a little bit useful.

Peter: The, the heart of your thesis is something that I think I tried to reflect on when I wrote Org Design for Design Orgs and in my own design leadership practice. And Jesse and I have talked about recently, even when we were back at Adaptive Path, where we tried to have just one role: You’re an experience designer.

And in that role, there could be a range of skills, and different people with the same title might have different skills, and that’s okay. Because we wanted to kind of support what you’re talking about. It’s less about you being tightly defined in this way and someone else being tightly defined in that way, and more this group of people is joining together to solve some problem.

As I’ve gone in-house, and then even after leaving, going in-house and becoming my own flavor of org designer, I found myself defining roles.

But, like, when I create career architectures, I always start with skills and not roles, where when you see, like, how most people create career architectures, they start with roles and not skills. But I start with skills.

I’m like, that’s the most important atom of effort, and then we can build a career architecture around that.

And so I largely agree with you. I also thought it was funny that something I’m seeing is that AI, and I put AI in quotes, is enabling many of us to dust off things that we were saying 10 to 20 years ago, and be like, “Maybe now. Is there… if we… Will you listen now? Because it was true before, but it’s actually even truer now.”

And I suspect that’s something of what you’ve got going on with what you’re writing.

Peter: But the part that I wanted… that maybe I disagree is strong, but where I’m like, the hard part of it is, I think, there’s these three qualities of roles that are really hard to get over.

Roles are human shaped, and I think as an anthropologist, I think we process the world, right, through heuristics, and one of the heuristics is things that are human shaped make sense to us. So a role makes sense to us in a way that a pile of skills doesn’t, and so we start there. It’s a human shaped thing.

Thing two is, roles are, to use Seeing Like A State language, they’re legible by the bureaucracy, right? The bureaucracy loves roles. It knows how to post a job with the role title. It knows how to put you in an org chart. It knows what to pay you, right? There’s just something about roles that get taken up easily by these systems, that again, a pile of skills or, like, five people on a team doing a thing, whatever that is, what do we call them?How do we pay them? What do we… how do we reward them? How do they grow in that career or whatever?

And then thing three is something you touched on, which is identity. This is something Jesse and I have been talking about, well, for 25 years, and pretty much since the start of the podcast, is designers…

Like our industry, our colleagues, many of them went to design school. They’ve had design in their title. They see themselves as designers first and whatever else second, employees second, an employee at a particular company second or whatever. There’s something around design that has this connection or affiliation with identity that’s so strong.

So my question to you, and this is a big one, but I’m curious your thoughts, like, how do we overcome these three kind of, obstacles isn’t quite right, but just, like, realities of role-ishness in order to achieve the nirvana of a post-role team-oriented future?

Clay: Yeah. That’s, it’s a very good question, and I’m happy that you… It’s okay to disagree with a thing too. I appreciate that it sparked this, ’cause it is worth debating and it’s worth digging into. I think in the three things that you identified, two of them are really good and worth maintaining as we redesign a thing.

Or if we move from where we are today to where maybe we hope to get, or where I hope to get with more of a team-oriented networked future for work, I think that’ll be better for more people more of the time.

So human-shaped heuristic for understanding the work that’s happening in a team, that’s great. I wouldn’t change that.

The identity thing I think can be, can be good for some people and limiting for others. Being constrained by the way that an organization sees you coming in, or by the way that the field has defined what you wanna do. In the case of organization design, we get defined by what big consulting says organization design is going to look like. And we have to, like, figure out our way around that.

So it’s good and bad, but it is part of who we are. Like, I wouldn’t wanna build a future that, like, sullies the things that make us human, right? We don’t want that.

Legibility to bureaucracy is the thing that I think is most worth figuring out in this. What do we make legible? How do you make an organization understandable to humans, understandable to machines, understandable to other organizations? You can put machines and other organizations maybe in, like, a bucket together because they’re only able to, like, piece together what they know about the organization by, like, sending a request.

But making, like, the organization and the work visible to each other, being able to see a system so that we can change a system, I think that’s really valuable, and it’s a slippery slope to creating something that feels like a surveillance state within an organization.

Jesse: Right.

Clay: So we have all of this exhaust coming out of the work that we’re doing.

Like, we know that the three of us were on this call together today. we could instrument that. It would be actually relatively easy for us to understand that we were on this call together, that we had these emails that preceded it, that I had read some of the work that you all had done, and maybe if we had all seeing memory of what we had been doing, it might be able to help us, like, make this better and make this more interesting.

But it would also mean that the organization would know all of that about us, and I think that’s a challenging bit of this. It’s like we have this ability, to your point, Peter, around, like, these ideas that we had a while ago that we knew were good ideas then but now have become relevant because the computer can actually do the things that would be necessary for us to actually bring that thing to life.

Okay, fantastic, and it has this kind of scary side effect. I’m not sure what to do about that, but I do feel like it’s something that we have to contend with in helping organizations find their way toward better structures that put teams at the center instead of saying, “Manager is a person,” versus, “Management is a valuable thing that we do, and many people need to be good at it.”

Even at the very top of the organization, they are managers. Almost to the bottom of the organization, there are managers. And everybody needs to be good at that. Leaders need to be everywhere. Subject matter experts need to be everywhere. So it’s, I think, just a better matching of reality to what we’re able to write down.

Jesse: Peter touched on our experiences wrestling with some of this stuff at Adaptive Path. And one of the things about that experience was, honestly, it pretty much worked. We had some challenges. We had some challenges with people who, going back to the identity thing, their identity wasn’t just designer, it was like, “Well, I’m not an experience designer, I’m an interaction designer,” and, “I’m not an interaction designer, I’m a service designer,” and on and on and on, where we had these sort of increasingly fragmented identities.

But in terms of how the work got done, it mostly worked. The people who were routing the work to the team knew the skills of the team and were able to manage that effectively and were able to assemble teams that could get a job done. That was at a scale when we were 30 people, 40 people maybe, and everybody knew everybody else. Everybody had worked with everybody else. There was a lot of the, kind of the intangible personal knowledge that was a part of our processes and how we made those decisions and how we made those choices.

And some of the things that I hear you talking about in terms of what do we do about the potential for these surveillance systems to shape this work, it seems to me that some of that is an artifact of scale, that you have to be able to architect these systems at a scale at which you’re evaluating the performance and evaluating the contribution of people who may be many layers removed from the people who are actually making kind of the big decisions.

And I wonder about how scaling can work when everybody is a pile of skills and every sort of interdepartmental or interpersonal contract is bespoke, so to speak.

Clay: Yeah. Great question. The prevailing answer in the scholarship and in the examples out there in the world is don’t. Just keep the elements small and knit them together with their own contracting and have something that feels more fractal in the way that it operates and the things that humans touch about it.

Like I’m with my seven people that I’m on a team with. I know them. I know them really well. I know that Peter’s really good at this, and Jesse’s really good at that.

And then there’s these other teams that I’m kind of like in a neighborhood with, and I know that they do that, and we do this, and this other team does that. And sometimes we do things together, and sometimes we do things apart, and they get value from us, and we are continually like negotiating that.

And then maybe outside of that group of 150, then there’s like, okay, that might be an organization. There’s maybe a bunch of teams within that or a few neighborhoods within that. And that way you don’t have to scale anything really, scale the human experience, but you’re able to build an organization that works well together because it can be knit together with something relatively simple, like a contract between a consulting client and Adaptive Path, or same thing with Undercurrent or August.

It’s through the contract, it’s through making something smaller, and it’s probably through building something that feels like a, like using consent in a different way than I normally would in org design. Like a consent-driven approach to like what’s disclosed by the individuals, what is gathered by the organization, and what remains like true to the person. What can they pull out of the organization? What can they determine they grant to the organization in terms of the information that they’re allowed to know about the way that we work, the kinds of things that we do?

And that networked approach that would shrink the interface, I think that might be the way out. I’m not sure. Yeah. I don’t think you can just try to import this stuff onto the top of a 50,000-person traditional command-and-control bureaucracy and have it work because people will want, “I need this thing defined. I’m here for a tour of duty.” The handshake is not between me and the company that I necessarily look up to and believe in the way that it would’ve been for Adaptive Path that makes things a little bit easier when people are coming in and more open to adopting a role that has like less clear definition.

Same thing with August, same thing with Undercurrent, et cetera. I’m not sure that it’s gonna work if we like have the same priors and try to import a system on top of it.

Jesse: Yeah. It’s interesting to think about the way in which if you kind of take down the level of clarity in the roles themselves, it has the potential to make the entire organization more nimble because people aren’t locked into a particular set of expectations.

I’ve been working with teams on their AI transformation initiatives for a little while now, and one of the things I’ve been saying to leaders is that this is a process of embracing the unknown, and in a team environment, it’s very difficult to do that if you don’t have a high level of competency across the team and a high level of trust across the team.

And the pressure on leaders now is to figure out how to create these high-competency, high-trust environments in which teams can rely on each other in the face of no contract at all, potentially, right?

Clay: Yeah. Completely agree. Completely agree. And I, I’ve ranted about this in a few different other posts and places, but it’s relevant to bring in here, too.

Clay: The trust thing, like leaders creating an organization that is high trust or that has a high degree of trust, means that there is trustworthiness between the organization and the individual. We have to say, “We trust you to try some things that are likely to be harmful to the organization, but we are interested in that because we are learning about how this new technology works. We have no idea. Anybody that does is wrong or lying or incentivized.”

And we don’t know where, like, where the motor in the example with the steam engines and electric motors, we don’t know where the motors are gonna go yet. We know that they’re gonna go in different places than we put the steam engines, but we don’t know where they’re gonna go.

And we have to dig into that by trusting our people and believing that they are more competent than we have believed they are in the past. I find all the time when I work with teams, that you give me 10 relatively junior people that the organization doesn’t think are all that great, and let’s put them in a team and do the things that we know to do to make them a team, to help them become a team, and they will achieve amazing things.

They’ll be seen as rock stars within the organization, if even if six months ago they were kind of like the cast-asides. Because people are capable. People are really good.

Peter: Just thinking of The Bad News Bears here.

Clay: Yes. I mean, it’s a sticky story. It happens over and over again because it’s real.

And I’ve seen it over and over again that just give me anybody. Doesn’t need to be the most talented people or the high potential people that the organization has determined are the ones who will rise up. Let’s see what happens. If we make them a team, they’re gonna do amazing things. It always happens.

It never doesn’t. It’s crazy. It’s not crazy. It’s super obvious.

Peter: So I have your book in front of me, Hidden Patterns, available wherever books are sold. And…

Clay: Thank you …

Peter: …you have as one of your foundational elements, something that I neglected in Org Design, but has since become core to my teaming practice, which is psychological safety.

And as you’re saying what you’re saying, right, there was the research that came out of Google a decade ago, maybe more now, Project Aristotle, where Google, a company built on high performers, right? Everyone is a rock star. Everyone has a PhD. Everyone is the best at what they do. And so there was assumption that the most effective teams would be those that had the best people on them as assessed by the system, and it turned out that was not the case. In fact, those were some of the worst teams.

Peter: But the best teams were those that had high degrees of psychological safety. So I’d love for you to actually talk a little bit about your experience with psychological safety, creating psychological safety, and I think it touches on matters of trust.

Our audience is a bunch of leaders who are probably trying to make a psychologically safe space in their organizations. We hope so. And one of the challenges I hear all the time when I teach my masterclass, we talk about psychological safety, and they’re like, “Yeah, so I can try to do that for my team, but we’re operating in a much broader context that just has none, totally lacks psychological safety. So what do I do then?”

So I’m curious kinda how you encourage, foment, enable psychological safety for those that you’re supporting.

Clay: Yeah. It’s really hard, and it’s poorly understood, and the tools that leaders are often given, I think, are relatively dissatisfying. I went to a workshop for HR leaders six months ago, and we were there with some of the psychological safety and design thinking luminaries.

They were teaching…

Peter: Did you ever think that you were just an HR leader? Did, did, in your wildest dreams 20 years ago, you’re like- … “My aspiration is to be an HR leader.”

Clay: No, and that is something that I deal with every day.

Peter: Sorry for the interruption. I couldn’t let that phrase go, though.

Clay: No. Speaking to the identity point it’s not something that I had envisioned for myself, but it’s been very interesting.

And one of the things that we were taught as a practice, which I love, it’s an amazing practice. I’d never done it before exactly. It’s a team kickoff thing where you get groups of three together, and the instruction for the group of three is for one minute, one person must say to the other people things that they love.

“I love Post-Its. I love this little fan that cools off my son when he’s in his carrier. I love going on podcasts.” Like that. And it’s really hard for people, very frequently, to get to the end of a minute and continue to have things that they love. But there’s also a lot of, like, commonalities that the facilitator will inevitably pull out.

Did people mention their spouse? Did people mention their child? Did people mention their career? Da, da, da. Did you have any similarities? And this is one of the things that we’re supposed to do to increase psychological safety, and it feels so rudimentary. It’s good. It’s good. I don’t think it’s bad. It just is one of those things where you’re like, “Okay. If we’re gonna create psychological safety, one of the things that I need to do as a leader is ask better questions.”

Okay. Is that the whole book? Is that everything? Well, kind of, and absolutely not, right? There’s lots of other things that we need to be able to do. We have to have, yes, good team kickoffs. We need to ask good questions. We need to model, as leaders, vulnerability.

Clay: We also need to address the structural parts. So if we’re able to, if we’re able to, as organization designers, get the keys to the top, the final boss, and actually do the deep structural work here. We need to address the lack of structural safety within an organization because you’ll have leaders within an organization that want to build psychological safety on their team, but they are not able to because that team could be deleted at the drop of a hat.

Peter: So that’s what you mean by structural safety as a distinction from psychological safety.

Clay: And we need both. We need both. And one of the things that we did and didn’t fully express in the way that I wanted to at August was set up a business where people have a very clear understanding of what will get in their way or what will cause them to be exited from the organization.

It’s by breaking these contractual boundaries that we have set up, and we all agree to them when we get started. They’re clearly written. We amend them only when we have the rights or the incredible data to change that constitution effectively. And that kind of thing, to me, is one of the reasons why August is still around 10 plus years on, right?

It’s an organization that has some durability to it because I think it’s spurred on even after founders like myself leave, because people feel structurally safe. So knowing what’s gonna get you kicked off the bus and actually knowing that that’s not like, “Oh, you did your expenses wrong,” but it’s like, “Oh, you weren’t trustworthy,” or, “You didn’t trust your teammates enough.”

Not that you spent too much money on this thing, or you made a bad decision, or the campaign didn’t work, or a client left, but that we couldn’t really believe in you as a member of this team, and people often found their way to leave on their own, right? So that structural safety that’s encoded into the organization, that is something that we need to establish.

Most organizations have nothing of the kind, right? You have all these things that you sign when you join that are, like, rudimentary guidelines about what’s gonna get you kicked out of any organization. Don’t do anything unethical. Those are important, but we forget about those. We don’t have anything that’s about the things that we actually care about.

So getting those things on paper, saying that we believe in them, actually believing them, and using them as the boundaries for membership, and then doing all the things that we need to do within a team, right? Have good clarity for what the thing is that we’re trying to do, what the rules of the road are within our team, how we meet, the way that we operate, asking good questions as a leader, kicking off meetings the way that we should.

There’s all these gigantic things and these really small things, too. So it’s hard, but it is the challenge, and great organizations and leaders who lead organizations that they believe in, I think, kind of do some of this naturally. It’s like, oh, we should have a skills framework for the way that we help people up level, but it’s not there to prevent you from up leveling.

We want you to use it. We want you to go, like, level up, become better. Those are the things that we know are powerful, and we just kind of neglect them. Sorry, that was a bummer.

Jesse: Yeah. Well, I’m maybe about to make it even more of one. When you talk about structural safety, it’s interesting because when I think about organizational resistance to change, it often is because of kind of the dark side of structural safety, which is that you have functions or business units or departments or other elements of the business that are sacrosanct, that can’t be altered in any way, that have been sort of calcified.

And I guess I wonder about how you manage that tension between wanting to create the correct amount of safety without encouraging this kind of rigidity structurally that prevents an organization from evolving and adapting in the ways it sounds like you were able to build in at August.

Clay: Well, it doesn’t work all that often, sadly.

You know?

Jesse: Hmm.

Clay: This is one of those things where I think those of us who turn our eye toward organization design tend to be really disappointed and feel like, “Oh my God, I didn’t actually want to do this.” This is not the way that I want to spend my time thinking about what to do with that calcified organization over there, and the people who are resisting change, and maybe rightfully so.

They might have some wisdom that tells us that we should keep it the way that it is, and the leaders around them that perpetuate that. Like, that’s… It’s ugly. Organization design is often dealing with the basest human desires and some of the things that we don’t like to express about the way that work works or doesn’t work for people.

And when it works, though, it’s by creating a movement toward positivity. I had this rule for… I still have this rule. I maintain this. Don’t convince people. Don’t try. Just offer the thing, offer the better way of doing something, offer the better design, offer the better practice, and if they don’t wanna do it, they probably have a good reason, and trying to trick them into doing it is not worth your time.

Instead, what’s better, a better plan, is to go find teams that really want to get something done. Lavish your time and attention and tooling on them, and then show the organization what they’re able to do. “Wow, this team over here was able to re-architect our backend. It would normally take a year. It took us 11 weeks.” “Fantastic. How’d they do that?” “Oh, well, they used AI in a different way.” “Oh, it was an actual team.” “Oh, they had a designer on the team.” “Oh, the PM was not just a PM. They actually had some, like, engineering chops.” “Wow, fantastic. Amazing.” And they added some more clarity to their team, and they’re able to agree how they’re going to operate together.

And then building up those stories, it becomes more and more of a communications thing, and I think that’s where we’re at with this movement toward better ways of organizing and better ways of working, is that we have to have more and more of those, and do less of the thing that I see in corners of this work, which is purity tests around the way that we’re working or the way that we’re thinking about it or the framework that we’re using.

Mm-hmm. And instead, just keep pushing for teams that are working better and showing that they’re working better so that we can get more leaders on the side for this. ‘Cause the thing that I see most frequently is that when you introduce some of these ideas to mid-level, like it’s usually not the top of the organization, it’s usually not the bottom of the organization.

The middle of the organization, someone in that room will look at you a particular way when you’re talking about, “Okay, we’re gonna create some clarity on this team. Management isn’t just gonna be a role. It’s going to be a practice that’s going to be distributed across the team, and you, all you people who have great skills, you’re gonna get to do those skills again more than you were in the past.”

One person at least will be like, “Uh, this is… I don’t like this. You’re changing the handshake that I made with the organization. I like what I do. I like doing it the way that I do it. I do not want to give up the management authority that I have earned over many… many years, and I don’t want to do SME work anymore. I don’t know how to do that. I don’t like doing it. These people do, and I’m a good manager of them, or I think I’m a good manager of them.”

And they’re right in that. They’re right in that. So letting them, like, have a graceful off-ramp from that or just not trying to trick everybody into doing the thing that you want to do because it sounds nice or it gets more done, that’s one of the hardest challenges in this work.

Jesse: Earlier, Peter touched on your book, Hidden Patterns, and this is a little bit of an unusual kind of a book. I wonder if you can tell us a bit about what inspired it and, yeah, some of the ideas behind it.

Clay: Sure. So it started in 2013 as an obsession with trying to break down problems of business strategy or corporate strategy or digital strategy or whatever it might be, into recomposable parts. So trying to understand the problem more accurately and then trying to resolve portions of the problem by finding solutions that were better fit to the form around it or the shape that we were trying to create.

That obviously touched on the work of, or was inspired by the work of Christopher Alexander, and I know that’s probably a big thing in your world as well.

And it was just rapturous for us to see problems in this new way. And we kept playing with that. It kind of became the root of the work that we did at August. When we got started with August and we started with one of our first clients, we wrote down all of the things that were working with our previous client work at Undercurrent, and we tried to make them as small as we possibly could so they could be recomposed into something that we could go deliver.

So we then rocked up to our big client and we were like, “Here’s our 50 things. We would like to go try these 50 things with some of your teams.” And they said, “Absolutely, fantastic.” It was our first client. We were so excited. And we got to, like, nine or so things that really worked. And I think August is still implementing roughly the same ideas.

So it’s this thing that has gone for me through multiple companies, has been a thing for me to try to take ways of working and break them down into not best practices, but patterns that preserve the context and tell you why you should be using those things and when they break and why you should modify them and, like, how they could fit together.

I had this idea that I’d been sitting on for a long time, and I feverishly wrote it and … ’cause I had all this material for it that was kind of like…

Jesse: Mm. Mm-hmm …

Clay: …poorly composed and things I’d half written or completely written and written seven different times. And I was able to, like, bring that into one thing and finally make the thing that I wanted to make that I would have wanted many years ago when I was getting started.

So it’s got, I don’t know, like, a intro that you can read in 30 minutes, and then 75 individual patterns that you can make your own, that you can remix, and that also are really interesting to play with with LLMs. You can use the stuff in the book, and I was intentional about putting it online for all people who have bought it and just tell me that they bought it, I give them access to the full text online.

Copy and paste it into your system of choice and use it to diagnose your problems. It’s cool to have something that feels like software instead of just a book of a framework that tells you the ways that you’re doing it wrong. So yeah, it was just kind of like a labor of love. It was, like, more of an art project than a business book, and when I was writing it, I had nothing to sell exactly.

So at the end of the book, it’s like, “Go work with my friends,” which I was very happy to do. So yeah, it’s a weird book. I love it, and it breaks things down from the biggest possible things like true purpose, structural and psychological safety, this weird thing that we encounter more and more every day, unfortunately, the idea of the importance of rule of law within the organization, and th- things all the way down to the physical space.

Thinking about the way that Valve puts all their desks on casters to let people move around to re-team with each other, and they couple that with the ability to actually dissolve the things that you’re working on and find the things that are most appropriate. So whiteboards everywhere and rule of law all in the same place, and everything in between.

Peter: Whiteboards everywhere. Very Christopher Alexander.

Clay: Yeah. Whiteboards every- ri- actually, it’s not whiteboards everywhere. It’s whiteboards at intersections. That’s the pattern, and I believe in that, and you notice the whiteboards that get used are in spots where people gather, and you end up seeing interesting ideas on them, and that’s the cool shit.

Peter: I’m curious of… You mentioned the 75 patterns, and you’ve identified a few. You highlighted rule of law, and that’s one, as I was looking at it, I’m– I’ve got my own project that I’m noodling on that I’ve realized is kind of adjacent to what you’re doing. I’m … I’m looking at a challenge that many who are listening to this will face is, and a question that often comes up is around, how do I make the company I’m part of more human-centered, right?

Jesse: Hmm.

Peter: Mm-hmm. And one of my missions in the work I do is enabling humanism within organizations. And so similarly-ish, I’ve been noting, like, what are maybe less patterns, kind of like criteria, components, elements, kind of these core operating aspects that either lean in towards humanism or lean away from it.

And been jotting those down, and then I’m between contracts, so I’ve been hanging out with Claude, throwing these ideas back and forth. But as I was getting ready for our conversation, I opened the book, I was flipping through it, and you have rule of law in there, which isn’t something that I had generated.

Like, the purpose stuff I’ve thought about, the psychological safety… some of the other things you’ve mentioned. But I’m curious, talk a little bit about rule of law, why it’s foundational. And you mentioned it feels hotter button right now to talk about it. Yeah. What is that?

Clay: Take a hypothetical organization Where there are different rules for different people.

Peter: Right.

Clay: And whether that’s a function that is better liked than another and is able to spend more lavishly on a conference that they want to go to, or a dinner that they wanna go out to, or that salesperson over there sells more than everybody else, so they get to do things that other people don’t get to do.

And this pattern, this idea of rule of law in the organizational sense, is just that we are going to live by the rules that we have written down, and we are going to adjust them when we have cause to adjust them. But we’re going to hold ourselves, regardless of the seat that we happen to be in, we’re gonna hold ourselves accountable to them through some mechanism.

Doesn’t need to be like a draconian mechanism, like, “Oh, if you break this rule, you’re gonna be out all the time.” It can just be, “Look, we’re gonna hold you accountable, and however we’re gonna do that, we’re gonna do that.” Might be a conflict management process, might be something else. And implied in there is that we are going to have a set of rules of the road that we actually think about, that are not handed to us by bureaucracy or by tradition.

So to me, it’s just holding ourselves accountable, everybody, to the same rules. Or if that salesperson over there does get unique privileges, write those privileges down somewhere and agree to them- Codify … so that other people can understand them. Once the rules are visible, people can challenge them.

That’s much more useful than making everyone guess which rules count. But Jesse, to your point a- around, like, fixing that ossified thing, fixing it starts with naming it and being able to address it, so there’s a few things that kind of like bleed out from the idea of rule of law, but that’s the…

Peter: all right, Wittgenstein.

Clay: …the idea. Sure.

Peter: No, I, I, you know, I wrote my whole book on org design because I realized you needed to define these things. And we tend not to recognize the importance of agreed-upon terminology, and then we end up talking past each other and then wonder why no one knows what’s going on.

I’m curious, though, as you were talking about writing it down, I wonder if you get the same kind of pushback that design has often got, uh, UX design has often got, which is you’re slowing things down. If we do, if we wanna do things your way, it’s gonna make us slower by following these rules and programs and processes of documentation or whatever, and we don’t have time for that.

And if so, if that is a common pushback, how you’ve addressed that?

Clay: Very common pushback. Yes. Why don’t we just get started? Why don’t we just do the work?

Peter: Yeah. Why do we need a charter? We know what we’re doing, right?

Clay: Yeah, yeah. I will usually have basically a contest. You take one of your teams, and you keep doing your thing.

Give me another team, and let me show you what they can do. And the numbers are… They tend to be outlandish. We talk about, oh, AI is going to be, like, this enabler of super performance for teams. We already have it. It’s just a good team. A good team is super intelligent. We’ve all experienced, in the best teams that we’ve worked on, this feeling of a hive mind.

That’s what we’re going for here, so let, let’s just do that. Let’s just do that more, more frequently. And what I find is, over and over, the teams that actually spend a bit of time getting their shit together up front, they end up delivering. Whether that getting their shit together is writing it down or whether it’s going to a mountaintop and becoming one with one another through time and place, I don’t care.

It could be either one of those or somewhere in between. But just do that and see what comes out of it. And they get… Again, the numbers are crazy. It’s, “Oh, we had a 4,000% improvement.” It’s like, “What? Clay, that, that can’t be true.” Well, it- … it’s very true. Here’s a project that we’ve done before. We did it Clay’s way.

It was so much faster, and everybody was thrilled, and everybody stayed, and they hired their friends. It’s just, it’s… Everything about it is better, and it is free. Teaming is free.

Peter: I’m curious then, actually ’cause I agree, and, and I think org designers can be a bit like Cassandras. We’re just shouting truth that no one is hearing.

But I’m wondering what you make of the resistance to it, right? In a world that claims to be data-driven or evidence-driven, why so many decisions are being made that actively thwart the stated desired outcome? And, like, how, just through your observations, what do you make of this contradiction between, you have evidence that a different way works better, and yet most organizations are behaving in ways that are antithetical to their own success?

Clay: I mean, I have dumb answers to that mostly, and they’re like, look at the world around us. You have to believe in state capacity and institutions and people and the fundamental goodness of people, and you have to believe that people want to get more done. You know, you have to believe that the road is publicly funded, and having a grocery store that’s publicly funded is also fine.

The world is not in our favor when it comes to this stuff. I think it is also just, it’s hard. It’s hard to do this. Building a team within an organization that wants to operate in a particular way, and the rest of the organization operates differently. Dealing with that dissonance, that’s hard on its own.

And then helping people get over, this is a thing we experienced at August, is nobody expects you to be true to what you believe when you believe the things that I think we do. When you’re like, “Every role in this team is going to hold equal stature regardless of their seniority,” people are like, “Yeah, okay. I’ve heard that before. We know this, how this is actually going to go, and I’m not gonna trust your word on this.”

And people, like, getting over their well-earned baggage around the way that organizations work, the way that people are asked to lead, that’s hard, too. It’s just hard. It’s harder. But it’s better, and I’m okay with that.

Jesse: But maybe just a touch of optimism can get people through.

Clay: Thank you. I… Funny thing was the first person who read my manuscript, he’s like, “It’s kind of, if you read it all the way through, it’s kind of a bummer, because every single chapter starts with, ‘This is why the usual way you do this is broken and terrible. Here’s a better way of doing it.” And I’m like, “Uh, it’s a little late to change that.” And it’s true, though. I do believe that, it’s a window into my, into my soul, I guess.

Peter: Though it’s also, I mean, another way to take the book is that it is utopian.

Clay: Oh, yeah.

I

Jesse: think so. Yeah.

Clay: Yeah.

Jesse: Yeah. Yeah. I think so. And I do think that implicit in it is the idea that if we believe it’s possible, then it can be.

Clay: Yes. Great podcast title, by the way.

Jesse: Clay, thank you so much for being with us.

Clay: Thank you, guys. I really appreciate it. And seriously, as a super fan- … it’s so cool to be here.

Jesse: Thank you so much.

Clay: I cared about intranets so much when I was young, in ways that, like… yeah. Anyway. Yeah. So anyway, thank you for doing the work that you’ve done.

Peter: Oh, thank you.

Clay: Yeah.

Peter: It’s been great to have you- Yeah … on the show. Thank you for not just Hidden Patterns, but the commentary generally on… Well, we usually ask, so let’s ask. Clay, how can people find you on the internet?

Clay: Most places, if you just search for Clay Parker Jones, you’ll find me. Current website, because I’m bad at managing domains, is cpj.fyi.

And with the help of my friend Claude, I was able to get all of the back history on the back issues off of Wayback Machine onto the current version of the site, which means you can go back to 2006 and read some really dog writing from me. Terrible. So, but it’s there.

Peter: Awesome.

Jesse: Thank you so much.

Peter: Yeah. Well, thank you for, for what you’ve contributed as well.

Clay: Thanks.

Jesse: For more Finding Our Way, visit findingourway.design for past episodes and transcripts, or follow the show on LinkedIn. Visit petermerholz.com to find Peter’s newsletter, The Merholz Agenda, as well as Design Org Dimensions, featuring his latest thinking and the actual tools he uses with clients. If you’re looking for help with AI transformation or you just need a private advisor to help you solve your hardest leadership problems, visit my website at jessejamesgarrett.com to book your free one-hour consultation.

If you found value in something you’ve heard today, we hope you’ll pass this episode along to someone else who can use it. Thanks for everything you do for others, and thanks so much for listening.

Are you a director-plus design leader looking to connect with others and grow your capabilities? Join Jesse and Peter for the fall cohort of the Intentional Design Leadership Circle, taking place on Wednesdays from October 7th through November 10th. Only 20 seats available for this live online program. Learn more and register.

Dr. Stefanie Hutka, design researcher, Berkeley educator, and author of What Your Machines Should Do, joins us to look to the history of industrial automation for lessons on AI transformation. From Toyota’s jidoka and the andon cord to Taylorism’s lingering grip, we explore why AI amplifies whatever conditions it finds, and why strategy and values must come before the tools.

Dr. Stefanie Hutka: https://sendfull.com/, LinkedIn profile, pre-order What Your Machines Should Do

Jesse James Garrett: https://jessejamesgarrett.com/

Peter Merholz: https://petermerholz.com/

Hey everybody, before we jump into the show, I wanted to share with you something that Peter and I have been working on. It’s kind of special. We have poured all of the thinking and all of the wisdom that’s come out of the last several years of this show into a six-week leadership skills development and support program that we call the Intentional Design Leadership Circle.

It’s happening October 7th through November 10th, and there are only 20 seats for this live online program facilitated by Peter and myself. Find out more information and get your seat at findingourway.design. Now, on with the show.

Jesse: I’m Jesse James Garrett,

Peter: and I’m Peter Merholz.

Jesse: And we’re finding our way,

Peter: navigating the opportunities

Jesse: and challenges

Peter: of design and design leadership.

Jesse: On today’s show, we’re joined by Dr. Stefanie Hutka, design professor, researcher, and author of the book What Your Machines Should Do: The Science and Strategy of Human-Centered Automation. She’ll share lessons from the history of industrial automation to observe models to follow and models to avoid as organizations move towards AI transformation.

From the humble loom to the factory floor to the values that underpin our processes, let’s go exploring with Stephanie Hutka.

Peter: Stefanie, thank you so much for joining us.

Stefanie: Glad to be here, Peter and Jesse.

Peter: To kick off, I think it would be good just to get a sense of how you introduce yourself. I know you teach, and you write, and you speak, and you work, and so, who are you? Who is Stefanie Hutka in the world?

Stefanie: Yeah. So I’ve been introducing myself by way of hats, that I’ve been wearing a couple of different hats. Hat number one, and arguably the largest hat, the top hat, if you will, is as a researcher. So I have even more sub-hats under that field.

I go back, to early days, my PhD’s in cognitive neuroscience. I was very much an academic researcher. I worked as a research scientist, found my way into design research, and that is primarily the type of work I do today at my consultancy called Sendfull, that I’ve been running for about three or so years now. So hat number one, researcher, specifically design researcher today.

Then hat number two is as educator. So I’ve been teaching at UC Berkeley, primarily at the School of Information, but also at Jacobs, the design school. I teach Introduction to User Experience Design. I just started my fifth year of teaching that to professional master’s students. I also have designed some new courses, including UX for AI and Designing Future Systems, which dove into some systems thinking mindsets and toolkits, as well as some strategic foresight.

And then the third hat is as author. So I’ve written various things over the years, scientific articles, industry articles. But most recently, I have a new book that is coming out, my first book: What Your Machine Should Do: The Science and Strategy of Human-Centered Automation with Rosenfeld Media.

That will be launching in November and currently on pre-order.

Peter: Wow. Jesse and I have been exploring the subject of AI and design, primarily design leadership, for the last almost two years now. And when we found out about what you were writing about we’re intrigued.

And so, unpack a little bit what the book is about for an audience of design and user experience leaders who maybe are still kind of grappling with concepts of automation.

Stefanie: For sure. So the book is a field guide for product and design decision makers to navigate this question of how do we automate and closing what I’ve called the automation strategy gap, where you have these dreams of fully automated futures and running after let’s automate everything, versus the reality of what’s actually valuable to our users.

How does this fit within their ecosystem? What is our organizational readiness? What is the actual capability of the tools at this time compared to that fully automated future? And so the book shares different frameworks and tools, some of which are derived from my own practice, some of which are derived from a synthesis of literature that I like to say is: it’s intended to be durable; it’s evergreen stuff.

This is not a book about how to use Claude Design or whatever tool’s gonna shift by the time this podcast finishes recording. I’m really looking at what can we learn across human factors, human computer interaction, management theory, cognitive science, and acknowledge that we are in a very new territory.

There’s many ways in which generative AI is unprecedented. Those three ways that I usually refer to that is: the unprecedented pace of development; the breadth of use cases that it can cover and what that means for human cognition and how much we can offload; and then the stochasticity of the output.

So it is definitely, you know… it has unprecedented elements. That said, we have been automating stuff, we have been building autonomous systems, for quite some time, so what can we learn from those principles so it doesn’t feel like we’re completely, you know, flailing as if there’s no prior, priors plural.

So the book is about those things.

Jesse: One of the interesting debates about this current wave of AI technology recently is the question of, well, how radical a change is this? And there is definitely this school of thought that holds that AI is, quote-unquote, “normal technology.” It’s just another wave of technological change.

It’s not very different from the things that have gone before. And then there’s this opposing camp, which is very much on the side that this is so fundamentally different that there’s not a lot that we can learn from the past, and I wonder where you fall on that continuum.

Stefanie: Yes. A little bit of column A or column B, or for my fellow design researchers listening, it depends. I think, you know, how are we, maybe how are we, defining AI, assuming we’re talking about generative AI, ’cause there are many types of AI. But yes, like the AI moment that we are in, I’ll start with maybe column B of what might be similar. So there’s something from one of your past episodes. I took notes on this ’cause I, I was excited about this conversation.

Jesse: She’s a researcher.

Stefanie: Exactly.

I was doing research, secondary research. This is what I do. The Paul Ford episode from a couple months back, you talk about compilers as an example of, now you have the sort of translation layer of intent going into the ones and zeros, and, we’ve had moments like this where we can articulate our intent in different ways that speed up our processes.

So from a technological standpoint, there have been big advances. We’ve had disruptive innovation. We’ve had mobile. We have had cloud. And those were definitely major events. We’ve had various tech bubbles before. We have navigated those. So we have, I think, from a disruptive innovation standpoint, we have some priors in terms of designing automated systems, like moving from human-in-the-loop to human-on-the-loop.

I mean, there are planes flying over us right now with autopilot systems that we’re presumably pretty comfortable. We’re not too worried about, how will the pilot lock back in with situational awareness when they need to? And we have figured some of these things out, so maybe we can learn from some of that.

So that’s what I’m talking about with some of those priors. Now, where I think AI is different right now is what I’ve called 10X cognitive offloading, and what I mean by that is, cognitive offloading is this just phenomena of delegating our thinking tasks to some sort of external device and often technology.

The classic example is Google Maps. I give this example. I bike to campus, to South Hall. I’ve been doing that route for five years. I’ve got that locked in. But the moment someone invites me, say, to Cheeseboard, which if you live in the East Bay, both of you know this, it’s not far.

It’s like a mile from South Hall, but I don’t do that trip very often, and I am entirely reliant on Google Maps. So I’ve offloaded my navigation capabilities to this digital map. And typically, when we’ve offloaded to technology, it’s been relatively finite in terms of our tasks, and I think the way, at least by default, a lot of these generative AI systems have been designed, like the phenomena of the prompt bar, it really invites kind of wholesale offloading, and we’re delegating the entire observe, orient, decision, act loop increasingly with agents such that if we are offloading, quote-unquote, “the wrong thing,” we can very quickly start to de-skill.

If we haven’t learned the thing in the first place, there’s gonna be a gap in our learning. And I think that getting to those three things I mentioned at the top of the podcast around one of those being the breadth of use cases to which you can apply this technology, I think that is where it is different, and combined with the pace and the inability for sort of slower moving systems, governance layer, for example.

We can’t build guardrails as fast as the tech is moving. I think that’s where things get unique.

Jesse: It’s interesting to think about that pace challenge for organizations as they are trying to adapt themselves and adopt these technologies and actually get some meaningful value out of them, in that the technology is changing so fast that organizations hardly have the chance to orient toward one approach before the state-of-the-art changes.

So if we put this in the context of a larger history of industrial automation, right? Where we’ve had increasingly more and more machines doing things that humans used to do, if we can define automation that broadly.

We are now in a place where there is this kind of… this shearing force where the technology’s moving so much faster than the organization that the organization fundamentally breaks because of it. And I wonder about, in your research, from your perspective, what we can learn from the pressures that have been applied to organizations in the past, from past waves of innovation that might teach us something about what’s gonna make an organization resilient now in the face of what’s happening.

Stefanie: Sure. So what immediately comes to mind is a contrast that I draw, in a chapter where I get into systems mapping, systems thinking, is contrasting Toyota production system with General Motors’ approach. So Toyota production system, one of the key sort of tenets of this is automation with a human touch, jidoka, comes from the Toyota founder, as a young boy, saw his mother working at a loom and saw that she constantly had to be monitoring this loom and invented this mechanism such that when the thread ran out or got stuck, the loom knew when to stop.

And this was ultimately like, fast-forward, Toyota moves from textiles into auto manufacturing. Japan devastated after World War II. American automakers very, very resource rich and you get to Toyota saying, “Okay, how do we move forward given our limited resources?”

And you have this approach to automation that’s very complementary to people. You have this idea of kind of the andon cord, you pull it if there’s an issue on the line and everyone comes rushing.

And I think that’s interesting because it speaks to kind of the values that the company sort of organized around. Certainly there’s contextual factors, there’s different geographical, region, and cultural values, so on and so forth.

And there’s a psychological safety when you’re pulling that cord that you feel like, “Okay, I can pull that cord.” So, that’s an example of maybe automation done arguably well versus a much more sort of Taylorist approach that I think we see with, General Motors as a contrast, but we also see in a lot of our thinking now.

So in contrast, you have this mindset from like the early 1900s, if we can atomize work and, we can easily swap someone out to do it, and I think there’s an underlying mental model that there’s limits to our human capabilities and, if only we can sort of automate the human error out of things, we will be more productive.

If you’re driving on the I-80, if you saw any of those Artisan billboards in the last couple of years, like “Stop hiring humans” with hiring intentionally misspelt to imply that we are error-prone fleshbags, I think you see a lot of that.

Yeah, I just threw in fleshbags to wake up our listeners.

You see some of that same sort of Taylorist mindset that’s very efficiency oriented, so you get this sort of trade-off between efficiency and effectiveness that comes down to the values in which the automation approach is grounded.

So I think the shearing forces are coming from maybe this sort of Taylorist orientation, and this is challenging because this is like the paradigm arguably, like the underlying mental models that may be examined or unexamined that are influencing the values on which the organization moves.

Jesse: You use this term in there, jidoka, which is a concept that I’m familiar with, but I think a lot of our listeners might not be, that is closely related to how this philosophy of automation was developed at Toyota, and I wonder if you can expand on that.

Stefanie: The Loom example is the one I go to, like, the idea of, you still have humans in the loop, but you don’t need to have them constantly.

There’s an element of there are things that are safe for machines, but there is a point at which the machine capabilities stop and, you need to bring the human back in.

It’s not necessarily any sort of value judgment, just like this is what the machine can do, and there’s going to be a point where the machine ends its capabilities and the human needs to take over.

Jesse: Yeah, I guess what I take from that is the idea that you build into the system the awareness of its own limitations and the awareness of when the system needs to stop and turn control back over to a human operator or a human intervention of some kind.

Stefanie: Yes. I was asked this similar question. I gave a talk yesterday morning. It was a Agentic UX summit, and one of the Q&A was like, “How do you know when the machine should stop?” It’s like, well, I’ve got a historical anecdote for you. Like back to your earlier question about what’s different this time, maybe the capability for adaptation of the system as you’re giving it feedback, like loops are all the rage right now, and we’re building agents, and this idea of there’s still a human sort of building that loop.

But if you’re optimizing the loop each time, the machine is doing incrementally more and you still need a human somewhere in there. But that dividing line isn’t static by any means. So I think that adds a new layer of challenge.

Peter: As you were talking about the Toyota manufacturing process I was thinking and I was doing a little research during that. There was also the work of W. Edwards Deming, right? It wasn’t just one person figuring it out, right? It was, like, this interesting confluence of thoughts and philosophies that led to things like lean manufacturing and the Toyota production process.

And the thing about W. Edwards Deming is funny is he’s an American who taught the Japanese how to manufacture cars because the Americans wouldn’t listen to him. He got no traction in the United States. Goes to Japan, teaches them, and then Japan eats our lunch, in the ’70s and ’80s.

Cultural contexts that encourage or enable a certain embrace of these tools and in maybe healthier ways versus less healthy ways, right? ‘Cause you also mentioned Taylorism, which is a bad thing, um, largely.

Like, I mean, you can make arguments for aspects of Taylorism, and efficiency’s not a bad thing in and of itself, but scientific management, when you go to those extremes, it becomes problematic.

What are you witnessing in terms of organizations’ ability to embrace automation in a healthy, good way versus perhaps in a toxic, damaging way?

Stefanie: Sure. So I see an experimentation mindset, like what I’ve coined because, gotta coin stuff when you write books.

Jesse: I don’t know anything about that.

Stefanie: Yeah, it’s like you’re building with intention, experimenting with intention is something that seems to be a hallmark of organizations that are embracing this change.

And I think there’s something that doesn’t get enough airtime, which is a psychological safety aspect of leadership saying “Hey, y’all can explore in intentional ways. We’re going to make space for this.” One of the most interesting examples that I saw in researching this is Canva’s approach.

They’ve had a AI discovery week two years in a row. So the fact that they did it again this year suggests that perhaps it was valuable last year, and it’s basically like the whole company shuts down for a week and just focuses.

The first year they did it in 2025, an educational aspect, and then like a two-day hackathon, and you have everyone from like the chefs to the engineers to the marketing folks to the legal folks involved in building this, understanding of capabilities together and building intuition around those capabilities.

And then this year it was a little bit more agentic focused and people building out parts of their workflow. And again, the fact that we’re gonna get everyone together, we are going to just get hands-on, and you can develop the sort of taste for: the machines suck at doing this, but they’re really good at doing that. Okay, how might we work together with this?

And so we can debate about how does that translate to product development and customer quality. But there is an element of the fact that that was sanctioned and that everyone is just like trying stuff out together and learning together. I feel like there’s something that echoes the andon cord phenomena where we can pull the andon cord, we all rush to see what’s happening.

I think according to the literature of this, the first thing that people do to andon cord puller in the Toyota scenario is thank the cord puller for highlighting the issue. And so, I think that’s perhaps a parallel around, yeah, psychological safety, experimentation culture. Yeah.

Peter: You mentioned psychological safety. So I’ve been doing a fair bit of thinking around how do you maintain quality in the face of AI? One of the common concerns that I’m hearing from literally every design leader is, “We’re producing more stuff, but it’s not any better,” right?

And it’s either them, their own teams are producing more stuff, or ,more often these tools are enabling product managers and engineers and marketers and others to essentially produce slop that now the design team has to hold at bay.

And one of the things that I’ve been noodling on is what I’m calling the creating the conditions for quality work.

So quality, you have a set of standards, but standards don’t live on their own. You need to have a set of conditions to uphold and enact those standards. And toppest most of the poppest most of those standards is psychological safety.

Psychological safety predates AI, you know, at least in design work.

It’s been shown just to be a core value of any effective work team. There was Project Aristotle from Google, pointed that out, that the thing that mattered more than anything else in how do you get a group of people to do good work together is psychological safety.

Not talent, not skills. Those were way down the list compared to do these people have that freedom to experiment, to try stuff, to fail, to push back on one another, as long as it’s in the interest of making the work better.

So that’s one of the thoughts.

Peter: On my whiteboard behind me, I have the phrase, “AI amplifies.”

Stefanie: Oh, yes.

Peter: I’m curious what your research has pointed out. My hypothesis, or my postulate actually, would be AI doesn’t meaningfully change anything. AI takes an existing condition and amplifies it. So if those existing conditions are healthy and positive and good, now those people are just generating awesomeness.

And if those conditions are toxic and negative and problematic it only gets more so quicker.

Are you seeing that in your work?

Stefanie: 100%. For better or for worse, yes, I am still on, Substack. And I had one viral note, and then wrote a piece following up on it, which was basically, AI is an accelerant. What are you feeding it?

And I think it’s– we can say accelerant or amplifier but this is 100% it.

The joke I make is, you know, AI, you bolt it on, it’ll either accelerate your dysfunction or also strategy. And I think when people are like, “Oh, we can build and find out,” yes, build and find out or ship and find out can work if you have a clear strategy, you have hypotheses, you have metrics that you’re going to measure, like was this hypothesis supported or not?

And presumably, you will only ship a few times and you will learn something, and you will adjust. But what I am seeing more often is, it is ship and find out, and it’s the same dysfunction as before, but now you’re burning out your customers with basically an endless A/B test.

So at some point, they’re gonna wise up to the fact that you’re just, like, you’re building a product strategy by did this work?, ’cause we can vibe code it and ship it now.

So I think all that said, l ike, all the goodness of AI: oh, you can work fast with small teams, and you have a strong strategy it is going to amplify that. You can build faster and get that out faster and iterate faster.

If you have dysfunction, it will also accelerate that.

And I think same thing with inequity, too. Thinking about people who have access to these tools or education systems or if you have curriculum where students are being taught how to use AI effectively versus there’s already existing dysfunction, like student to teacher ratios, and students are just like using AI to write their essays ’cause they’re, like, time scarcity or don’t get enough attention, it will accelerate that inequity as well.

So yes, it’s a bolt-on accelerant amplifier. Choose your word here.

Jesse: Mm-hmm, It’s interesting the way in which it does amplify both the positives and the negatives within an organization, right?

And then in some ways for leaders, what that does is that makes it ever more glaring, the rocks that have been just underneath the water that maybe they didn’t even see, and it asks leaders to maybe let go of some dogma, maybe let go of some ways of doing things that have served them really well up to this point.

And I find myself wondering about adaptation and what it takes for leaders to adapt their own thinking to create space for some of the things that you’re talking about, the experimentation and the safety, the ability for the team to take chances, and how the leader might need to change what they do in order to make that possible.

Stefanie: Yes. I’m connecting this to this concept that I talk about in the book, which is going from AI-first strategy to strategy-first AI.

And we can argue that strategy, as defined by Martin and Lafley, the series of choices that you make in effort to pursue some sort of winning aspiration.

Like, where do you wanna play and how are you gonna win, and how are you using AI to support that?

So I think there’s a connection point between, okay, you gotta have a strategy and know where you wanna go, but also stuff is changing so quickly that is Horizon three even still a thing, or has it just been smushed down?

So I think there’s like this inherent tension of how fast things are moving and how that leads to what is our strategy, or how can we see around the corner, and there’s all these other, like, macro factors impacting where we wanna go.

Jesse: It feels like there’s something there in terms of how leaders balance their time and attention. So if you’re in a leadership role in a product development organization, it used to be that your job was basically to keep the process buttoned up, and to make sure that everything went according to some predictable cascade that was something that was repeatable and you could be held accountable for as a leader.

And now it feels like it’s much more… Peter and I have used the surfing metaphor in the past, where it’s much more about your ability to flexibly respond to the changes that are going on rather than your ability to set an expectation, and then drive a team through a process in a way that fulfills that expectation.

So when I think about, yeah, when I think about the skill set, I guess that’s where I wonder, like, how do leaders need to think differently about the work that they do?

Stefanie: Yes. I love that the surfing metaphor, my editor was getting sick of all of my white water rafting metaphors. I happened to have written chapter six, which is about strategy and AI, in Chile in Futaleufu, which is known for some of the best white water in the world.

So yes, this flexible adaptation and I think maybe this metaphor of steering that, like, Terry Winograd coined that many decades ago. But how do you steer in the rapids?

And I think that mindset, there is definitely an embrace of ambiguity.

This goes back to the psychological safety piece, trusting that you have certain values. I think being very, like, value-centric ’cause again, to go back to my overused river analogy, when you are in the current, when you’re in white water, it’s like you can have the best laid plans, but it’s really, what are the sort of embodied values in that case of your procedural memory.

But here when we’re in those river— like, what do we stand for as a company? Do we, do we value quality? ‘Cause that’s the thing that’s going to be how you’re gonna navigate around the rock.

So I know I had this great back and forth with one of my tech reviewers ’cause I was talking about vision versus values. ‘Cause vision is dependent on seeing the future and if we’re not sure if we can confidently see too far out into the future, that falls apart a little bit. But if you have values, that can guide behavior when you are surfing/steering/white water rafting.

Peter: You used the word stochasticity. That is an easy word to say.

And I wonder if the stochasticity is related to this because, you’re not quite clear. You’re not certain. It is not determinist what is coming out of this system, so you have to be willing to kind of bob and weave with it and nudge and course correct it.

It’s very cybernetic. There’s always a dialogue as opposed to you do a thing and then it’s done. Is that a fair connection?

Stefanie: That is a fair connection. I love that because I was thinking of it primarily at the… what is a tool and the quality of our tools being stochastic has all of these bidirectional influences on our ways of working on systems, like macro systems, so on and so forth.

So I think that’s a very fair connection and I love that, and that’s something that I will be mulling beyond this call.

Peter: When you were talking about the Jidoka and the Toyota manufacturing process, and part of its reason for being is it came out of a resource-constrained reality.

And I think, likely the reason the United States did not embrace these approaches is because we had the resources. We’re not constrained. We don’t understand an approach that assumes resource constraint, whereas the Japanese that was where they were starting.

And I’m wondering, what is the analogy today with generative AI tooling in these environments and resource constraint?

I’m asking in part because I’m working with a bunch of massive legacy enterprises, hundreds of thousands of employees. They are not in any way resource constrained. I mean, the designers always feel like there’s not enough of them to do the work given the amount of work to be done or whatever.

But in any legitimate context, there are plenty of resources. That’s not the problem.

And I wonder if that’s actually why a lot of those companies are struggling to embrace AI, not just because of bureaucracy and legacy ways of working, but a philosophy or a need that just doesn’t exist for them. Whereas startups or earlier phase companies or entities that are struggling, there’s some, I don’t know, to overuse perhaps now a supposed Japanese philosophy of beginner’s mind, right?

Like there’s some willingness to really embrace this approach for what it is meant to be, as opposed to slapping it on or bolting on because you’ve been told, but it’s not really suitable given your context.

Jesse: Right

Peter: But those Japanese manufacturing processes or practices were born of resource constraint. What do we learn from that when trying to apply automation tools in an environment that maybe isn’t resource constrained? Does it just mean you can do more or is that a misfit? Is there something actually ill-suited to a resource-full environment and these kinds of approaches?

Stefanie: Ooh. Yes. So I’m thinking about what is the incentive structure to bring in that technology if you have unlimited resources. I think it’s a lot of the maybe incentive structures, our old processes and maybe reluctance to adopt new processes that is creating resistance, and maybe it’s just, like, how information flows.

It’s like the double-edged sword. If you have a big organization, there’s more information flows, it’s harder to institute processes.

So I think there may be an element of what we have seen historically, like when you brought in electricity instead of a steam engine into a factory, you know, decades and decades ago. It took 40 years for the ways of working to adapt to that because you didn’t redesign the factory.

And so is that related to constraints? I think it’s maybe getting very excited over what are the technical capabilities, but not realizing that the people side of it needs to change. We are sociotechnical systems, and you gotta give the socio part of the sociotechnical some love as well, and there needs to be this joint optimization.

And so I think that’s, if anything, what I’ve seen more in the research for this book, which is the over-pivot on we can automate all of the things, but not realizing that that also materially changes how we work and how we collaborate.

If roles are blurring, okay, we need a new process. We need maybe different team formations. We need maybe to bring in maybe different types of expertise. And so that’s more so how I’ve seen this show up.

Jesse: When I think about these large-scale enterprises, honestly, what it comes back to for me is they know too much, they’ve seen too much, they’ve been through too much. They have accumulated so much latent wisdom inside these organizations about what it takes to deliver whatever it is that they’re there to create.

And it could be 3M, it could be General Motors, it could be General Electric, it could be Verizon. Like, It could be any of these very large-scale organizations where, yeah, you know what? We’ve got decades of experience that tells us what it takes to deliver at scale. And this stuff flies in the face of that.

And for you as a manager to stand up among your peers and say, “We’re gonna ignore the 120 years of background and experience that we have in what it takes to run a railroad or an electrical grid or whatever the large scale thing is that you’re doing,” there’s a risk.

There’s a political risk that comes with that, and it means standing up for a value prop that may or may not even really be there.

And so I find myself wondering about sort of the chilling effect inside organizations that potentially limits leaders from stepping into the capabilities of these things because it means flying in the face of decades of wisdom

Stefanie: Yes. I’ve seen some of this in my interviews, like primary research for the book around folks who have successfully navigated this just around small AI pilots just saying, “Okay, we’re going to start small. We’re not going to necessarily redesign the entire factory, but let’s use this sort of like little cupcake. We’re gonna do the cupcake of the cake in this area. And this is the runway I need. This is what we’re measuring. And if that goes well, that can be a sort of safe way to introduce that if you have someone who’s going out.”

I’m sure you’ve seen, some of this as well.

But I think, yeah, absolutely that, is true. And then of course, no one is speaking up because they’re worried that that won’t go over well, and all of a sudden you have the company continuing to operate for steam when it needs to be adapting to electricity.

Peter: I think the risk frame is interesting because of the stochastic nature of AI.

Businesses love certainty and dependability. And so you might think that they would fear AI because what it produces is often uncertain and out of their control. But for some reason, businesses have just decided to massively embrace AI before really understanding the implications of doing so.

I think with the promise of automation and frankly firing a lot of people and cost savings.

And so it’s identifying this internal contradiction going on within these businesses. Like, there’s risk aversion to a point, but I’m willing to take that risk if the amount of money to be saved is just orders of magnitude.

You also mentioned values earlier, that there was some underlying value that maybe we hadn’t yet tapped into that is now being expressed when they’re behaving like, “Oh yeah, actually risk has been fine. Look at how we’re embracing AI.”

That means it’s not that risk is fine, but firing a lot of people is even finer or something.

Stefanie: Yes. Oh my gosh, yes. I have so much. I have, I have… Our listeners cannot see my little squiggles, but there are two squiggles on top of each other, and they represent leadership and builders talking past one another, And this gets to one of the keystone frameworks from this book, this autonomy decision matrix, that ultimately the axes are could you do it and should you do it?

And it’s designed to be the sort of common language where you have, okay, we wanna automate X, we wanna automate customer service. What does that even mean?

And so that you can ideally, if you have both parties or representatives from both parties in the room, you can hash out what are you actually talking about, ’cause I think we have dreams of fully automated futures, we need to report to shareholders at the top layer, and oh my gosh, AI can do all of these things.

And then to the stochasticity point, something that was coming up in the book is that even builders, like folks who are very technically skilled, they don’t even sometimes know the full capabilities of this tool. They’re like, “We’re still figuring it out.” So when leadership is like, “Let’s automate customer service,” and builder’s like, “Oh, wait a sec, no, that’s definitely…”

There are a lot more humans in the loop than you think, and probably will be for a much longer time, and they are talking past one another, but then there’s top-down mandates happening, and you get all sorts of weird stuff being like, “Here’s our spreadsheet of AI features,” and “Let’s start jamming those in according to a roadmap,” and just, you start getting this sort of breakdown from that initial talking past.

So one of the tools from the book, it is an attempt to be a common map so that you’re looking at how confident are we that we could do it from a capabilities and readiness perspective, and then from the should do it, what evidence do we have around, customer needs, et cetera, et cetera.

And we can actually plot this thing on a two by two, this thing being what we’re talking about automating, and starting to get precise.

Okay, when you say customer service, what tasks in customer service? What percentage of things are we trying to automate? Is it 80% of routine requests? Okay, what, how do we define a routine request? Can we go back into the data and define it? And all of a sudden you’re like, “Okay, maybe we can do 40% of that now, but we need to build a triage system today to go back to humans.”

I think is related to maybe some of the uncertainty at the builders level, and that is creating tension when you’re going back up to the leadership.

Peter: Well, right, ’cause the leaders expect this to behave like any other determinant technology, and the builders realize that’s not how this works, right?

Stefanie: Yes, exactly.

Jesse: When I think about these legacy companies and what the history of those companies has taught them about what it means to be successful, it feels like there’s a place where the technology starts to hold a different kind of meaning here because of its unpredictability, because of its stochasticity, because of the way in which we’re all now sort of, when I was leading AI work for Capital One back in the day, I used to say that this work is, it’s not about being a dog trainer, it’s about being a lion tamer, in the sense that the dog is eventually trained, the lion is never ever tame.

And so the work continues on an ongoing basis to manage and shape the unpredictability of it. And the decision-making cultures in organizations when nobody can know for sure what is actually gonna go down. And the implications for how decisions get made, what inputs come into those decisions, and what voices, to your point about the builders, what voices are involved in those decisions, whether there is actually a change that needs to happen in decision-making culture in order to actually leverage this technology to its fullest potential.

Stefanie: I love that. On my little blue piece of paper, I have a very rough and scrappy little stakeholder map with bubbles, and I have builders, I have leaders, and I wrote investors. We could put shareholders there if you want to. And the only reason I put them on the map and brought them into the mix here, I’m actually not betting against larger organizations, that, like, small organizations that are AI first are going to win out.

But I think that investor perception plays into this dreams of automated future thing, ’cause if you’re like, “Oh, there are these big companies,” they might be trying their darnedest to integrate AI in meaningful ways. But there’s this idea that because you can automate all of the things so quickly, you can cut out that middle layer of management, and you can just fire a bunch of people, and so therefore, smaller companies inherently will be able to do the same thing as larger companies.

Like the hill that I die on is there is a layer of tacit knowledge and situated action that like generative AI with large language models, there is an absolute ceiling. Sure, capabilities are getting better every single day. We can automate more than we are doing now, but there is a ceiling, and that information flow, you will still need those large organizations.

But the investor perception that we can automate all the things adds to the sort of preconditions that leads to the dreams of automated futures. And so anyhow, that is worthwhile to mention in like the pressures those larger organizations might be feeling and reacting to, which may not actually be true of even what is happening in the building.

Jesse: Well, it’s interesting to think about, what is the kind of the upper limit of all of this?

Stefanie: Oh, yes.

Jesse: Like just in the digital space where you don’t have factory floors to maintain, there are no chip fabs or assembly plants or shipping or logistics or any of that kind of stuff.

It’s just data. It’s just ones and zeros being produced. It leads to a question like, well, how few people could you run Facebook with? Like, how small a team could potentially enable a global offering? And in that case, what are the humans on that team doing and what are the robots doing, right?

Stefanie: Yes. So yes, how small, I won’t give you like a absolute number, but I’m thinking about the subject matter expertise of someone in, I don’t know, someone in legal, someone in software engineering, like that deep well of knowledge.

I think there are certain things that are not machine readable. No matter how much you, hook up your Slack or your email your, whatever’s in your knowledge base, the meeting that happened after the meeting that actually informed the decisions, probably not in that knowledge base.

The sort of embodiment aspect of just our being is not in that knowledge base. This is why I’m a lot more interested in, say, world models or even like biological models, There’s a lab in Singapore, very sci-fi, building this. But like there is a, there is a limit of how much of that knowledge you can make machine readable.

So at some point, if you’re building something that is more complex, maybe you’ll need fewer people, but you will still need some expertise steering these machines. So will you have a fully super dark factory? Like a, like level three automation where you have a super dark factory that’s basically like a child or like you’re someone who’s just autonomously navigating and forming their own goals.

There is no example of that yet, but I’d argue that we cannot get to that unless you’re literally just recreating people. And so will organizations be smaller? Yes, but they will not be as small as we might think.

Jesse: I love imagining the future headline, “Rogue automotive plant starts manufacturing kitchen appliances,” right?

Stefanie: Yes. No. It, it does raise the, yes, it has, it has formed its own goals, and it is now…

Jesse: Mm-hmm. It’s decided this is the business move.

Stefanie: Yes, exactly. That is… Is that AI first strategy? Very literally.

Peter: You guess?

Jesse: Yeah.

Peter: Very, Very much so. Not wholly unrelated, but behind me on my whiteboard is the double diamond.

And it’s up there because when I talk to design leaders, I find that it’s a way to talk about AI and design and user experience in the modern workplace.

And given that you are teaching the next generation of folks who are going to be practicing this, I’m curious how what I’m about to say lands.

And with the double diamond there are two vertical lines in the middle of each diamond. And the idea is when you’re on the left of the front diamond, the people doing that kind of work in strategy, in ideation and concept development, fucking love AI.

I did this listening tour of design executives and what I’m saying comes from conversations with one in particular, but others have agreed as well.

Strategists love th-these tools. They love being able to produce visions of near futures, six to twelve months out. Put real information, real data in those. Put those in front of real people, get real responses, iterate on them in a safe prototypy way and start even building the thing, right? The tools are affording those abilities. So you have this strategy team that’s embracing AI because of the just more rapid sense-making and you don’t need to coordinate as many other people. You can do a lot more on your own in terms of figuring out some strategic work.

And then on the back half of the second diamond, the kind of delivery and ship parts of the process, that group is loving this because they’re now in Git, they’re now making pull requests, they’re now shipping code.

And that chasm that used to exist between even a design technologist and an engineer has just, in many organizations, shrunk or super blurred. There’s not a chasm anymore. You’re just walking from thing to thing.

But what’s happened is the folks in the middle of the double diamond are the ones who are struggling because partly they’re feeling it on both ends, right?

If the strategists are able to do good enough UX work, and I’ll call the middle of the double diamond, the end of the first diamond and beginning of the second , the UX-iest part of this. The strategists are able to not just produce prototypes, but they can then turn that into something that looks and works pretty well.

And the design technologists to front-end developers or the UI designers are able to kind of back up their work in using design systems and whatnot, kind of assemble a perfectly good experience.

And so the people who tend to operate in the middle of the diamond are getting squeezed.

At least this is what I’m hearing from some folks. I’m wondering how that framing lands for you, how you are thinking about the roles in user experience and design work as you’re having to be very intentional about it in the teaching mode that you sometimes operate in.

Stefanie: Yes, I have. I think being in that middle, like, when we talk about UX roles and I think we’re saying that UX as a discipline remains important. However, the roles certainly are changing in how they’re defined, and I feel like being in the middle of the double diamond is an artifact of what has happened to UX, like post-Agile, post-commodification with design boot camps, et cetera, and so on and so forth.

And how I am teaching design, I think, in many ways goes back to, like, the earliest conceptions of UX like, you know, sort of Adaptive Path, early user experience architect, and, going even farther back into the history of human factors of HCI and then service design feeding into that. A much more expansive definition where it is like, no, understand how both diamonds work, maybe have a deep well of knowledge on one part of this are you drawn to? But I don’t want you to go out into the world and just be operating at that middle layer, which is what many students who come into the classroom think they’re about to do.

Like I have Jesse’s Elements of UX diagram. I think it’s in our second lecture, and the assumption for many of the students are that UX is the top layer. It is the visual maybe design layer. It’s very execution.

Peter: I’m sure Jesse wants to comment, but I’m not gonna let him.

Because you mentioned his elements. So on my drawing of the double diamond, it might not be obvious, but I drew the five elements,

Stefanie: Okay.

Peter: And I talk about how those top two elements are what AI does really well, right?

So, so the visual and like the top el- elements of UI design, AI can do those.

And so when I think about the middle of the double diamond and the work that was UX, what I see is still an opportunity for those who might not find themselves at either end, or just an opportunity generally, is to go deeper into the elements of user experience.

Because for so long, digital product design has been so focused on UI that what all the tools are trained on is that, and they don’t know how to deliver quality structure, right? They don’t understand IA, they don’t understand real flows and conditionals and all that kind of stuff that leads to a robust software experience, right?

Everything got very superficial over the last 10 years in terms of these digital tools. If it’s more than you tap a screen, do a thing, and then tap back out, like these systems tend to be too hard to use.

And so part of me then is wondering, and I’m wondering if this comes up in your class, right, is there a renewed focus on the deeper elements of user experience given that AI is able to automate those top parts?

Stefanie: Yes. Oh my gosh. And I have a anecdote, so not to super flex. I get great teaching evaluations, but there was one critical piece of feedback maybe two years ago from a student, which was like, “This was too much of a UX research class.” And I think they’re attributing it to me being a design researcher.

I’ve made great pains in subsequent years to highlight that the bottom of the diagram is user needs, and that is how we determine the goals.

If you are making your text larger, it is ’cause you’re moving the user spotlight of attention ’cause it is related to their goals. Or if you’re using color to draw attention, like, it’s all connected.

And I think that is– I know as a researcher, obviously I’m very excited about focusing on that, but I do wanna emphasize that to students throughout that process you’re constantly doing research.

You’re tying it back to who is in this experience and trying to build a very, I think, holistic understanding of what is context. I think that is something that is lost, like the ethnographic nature of design research. I think that is quite new to folks in many cases if they’re not coming from a social science background.

So I certainly do emphasize that throughout the process and remind folks not only that there is a foundation to that diagram, but that they all ladder upon one another. You can pull that thread.

Jesse: So over the course of this conversation and indeed your book as well there’s been this recurring theme of connecting back to what’s gone before to learn from the history of automation and the history of organizational change related to it in order to make better choices going forward

I wonder about the parts of it that we can’t predict, the parts of it that are genuinely new. And for you, from your perspective, I wonder, what are the big unknowns that you’re interested in seeing the answers to over these next few years?

Stefanie: Sure. One of the big unknowns is to what extent will we be conducting, quote-unquote, user research on machines? This came up in several of my interviews around what is the output from machines? What are the gaps in the output? Can we do a log analysis of what’s coming out of our machines so we can understand either bias patterns or kind of understanding almost like the machine psychology. I think that’s kind of interesting.

I brought in a friend from IDEO who wrote a paper on synthetic users to do a Q&A with my class, and then got into a whole back and forth on LinkedIn with another practitioner, in a good way about the role of synthetic data in innovation in the earlier… in discovery.

And right now, I think that common wisdom is that these are regression to the mean machines, don’t use synthetic users, you know, LLM personas, like, random machine’s idea of a 23-year-old’s attitudes about iced coffee. Like that’s not gonna be predictive of actual behavior, so don’t make decisions based off of that.

But there are, if you look at, like, large data sets around okay, if we have a lot of historical user behavior and we’re essentially treating a synthetic model as a database that we are querying, maybe there’s actually some utility.

So like this gets to, to what extent can we bring in synthetic data earlier on in the process, I think is really interesting. And like right now, I can share if you want in the show notes, there’s a paper talking about like predicting how well prototypes will resonate. It was actually in a like scent study of all things, like different fragrances.

Peter: Oh, not even information scent…

Stefanie: Exactly, not even information scent, actual scent.

And it was like quite accurate, but, you know, it was very bounded. And there was a lot of historical data. So I think that’s interesting.

Something that was brought up from a guest speaker from Microsoft in my UX for AI course, he is designing computer use agents and I think my students’ minds were blown apart a little bit by the idea of having a persona or two personas, one of whom is a person and one of whom is an agent.

And that’s really kind of mind-bending, I think in many, many ways. And do we accept that? And is that, is that responsible? Should we be doing that? Is it just a reality? So that’s something that I’m really curious about.

And then I think maybe a fourth thing is designing for physical AI. I know we’ve talked a lot about, presumably, software based AI in this conversation, agentic systems and assistants, so on and so forth.

But where I’m very curious and a lot of my background in industry when I’ve been in-house has been working on spatial computing products, so augmented reality, virtual reality, a lot of the same technologies that make that work apply to robotic systems like visual inertial odometry and like spatial intelligence and all that sort of stuff.

And I’m really curious about the role, especially of industrial design coming back into the fore and designing interaction patterns for physical AI. I’m curious about that deep understanding of context. I think we will need, by necessity, to double down on ethnography if we’re designing household robots like Nome from Frog, I think is a really nice example of this, of a companion robot that goes around and picks up your kids Lego pieces or, stuff on the floor, and it looks kind of like a cute little coat rack.

It’s not a humanoid. Of the things I mentioned, I think that’s what I’m most excited about. I see that really requiring sort of that holistic UX and design mindset and skill set to design what’s coming after the more software based AI situation that we’re in.

Jesse: Dr. Stefanie Hutka, thank you so much for being with us.

Stefanie: Thank you so much, Jesse. Thanks, Peter.

Peter: Oh, this has been fantastic. Thank you for joining us.

Stefanie: My pleasure.

Jesse: If people wanna find you on the internet, where can they find you?

Stefanie: Yes. You can find me first and foremost on LinkedIn. So if you look up just my name, Stefanie Hutka, feel free to connect with me there. I also publish a biweekly Substack that is Sendfull, S-E-N-D-F-U-L-L, and you can check out my book, What Your Machines Should Do, which is now available on pre-order and coming out in November

Peter: And tell our listeners how important it is to pre-order books.

Stefanie: It is incredibly important to pre-order books. That is all. But yes please buy books. Please leave Amazon reviews. Yes.

Peter: Awesome

Jesse: Fantastic.

Thank you so much

Stefanie: Thank you both.

Jesse: For more Finding Our Way, visit findingourway.design for past episodes and transcripts, or follow the show on LinkedIn. Visit petermerholz.com to find Peter’s newsletter, The Merholz Agenda, as well as Design Org Dimensions featuring his latest thinking and the actual tools he uses with clients.

If you’re looking for help with AI transformation or you just need a private advisor to help you solve your hardest leadership problems, visit my website at jessejamesgarrett.com to book your free one hour consultation.

If you’ve found value in something you’ve heard today, we hope you’ll pass this episode along to someone else who can use it. Thanks for everything you do for others, and thanks so much for listening.

Peter and Jesse are joined by Chengying “Z” Zheng, who shares her experience migrating a design team to be AI-first — off Figma and into code. She discusses how design leadership and operations divide the work, what happens to roles and titles when everyone becomes a builder, and how to make good design easier than bad design.

Z on LinkedIn: https://www.linkedin.com/in/changyingz/
Z’s Substack: https://changying.substack.com/
Jesse James Garrett: https://jessejamesgarrett.com/
Peter Merholz: https://petermerholz.com/

Jesse: I’m Jesse James Garrett,

Peter: and I’m Peter Merholz.

Jesse: And we’re finding our way,

Peter: navigating the opportunities

Jesse: and challenges

Peter: of design and design leadership.

On today’s show, Jesse and I are joined by Chengying Zheng, better known as Z, the design operations, or should I say experience operations leader with extensive experience in tech. She shares with us how she guided a design team through an AI transformation, setting aside Figma and building right in code, her thoughts on the evolution of roles and teams, how to maintain quality, and the new work of operations.

Hi, Zee. Thank you for joining us

Z: Thanks for having me

Peter: The conversation we’re having with you, for me at least, started, I wanna say, six to eight months ago, when you and I were in the offices of Figma at a gathering. There was a lot of folks there, but you and I had peeled ourself away from the crowd, and you looked at me, you looked around, you looked at me, and you said, ” It’s a little weird for me to be here because I just spent the last three months or so getting my team off of Figma and into AI tools.”

And we talked a fair bit about that. You’ve been writing about it in your newsletter, but I’d love for you to share the, the highlights of that experience. Yeah, the highlights of that experience. Explain a little bit about where you were and what that journey was like and how you did evolve a team out of Figma and into more kind of AI-native practices.

Z: Yeah, absolutely. It was a really interesting moment. I remember that conversation

A lot of folks at the time were talking about AI transformation. Everyone was thinking about it. This was still last year, still a little bit early in this curve about AI transformation, so a lot of people were thinking about it, and people were doing it, and some, of course, AI-native companies were way ahead compared to the rest. They were already out there.

And our team was interesting because we had this mandate, like any other tech company, right? So you will start to do AI transformation, to incorporate AI into your workflow.

So for designers, the first thing that we looked at was how designers prototype. We weren’t even thinking about how designers ship, we were talking about prototyping.

And of course Figma has been the de facto tool for product designers for many years by now, but in this new workflow, we were thinking about getting designers to prototype with the new capabilities, with all the vibe-coding capabilities.

And a lot of our designers started to see that Figma, instead of a prototyping tool, which is what we used it for before, had now become a wireframing tool. Basically, you come up with ideas and then draw them out in Figma, but then you- the prototyping is actually happening in the coding part, in the vibe coding, whatever the tool was back then, whether it’s Claude or OpenAI, whatever.

So I wrote about it. I audited our Figma. Of course, as the operations person, we look at our Figma usage and everything. I audited it one time, just on a random day, I looked at it. Out of our hundreds of licenses, there were 50-some people using it that day, and only five of them were from our product design team.

Most of the others were marketers, PMs, everything. So that was a very interesting moment for us to look at tooling and at the designers’ tool stack. But that was months ago, actually, compared to right now. Everything moves so fast, and that feels like so long ago.

Jesse: I wonder about the cross-functional aspect of making this happen, because there is always this sort of ripple effect whenever one team changes the way it does things, on how that team then interfaces with the teams around it. How did you manage the cross-functional conversations as you were transitioning the team out of Figma as their primary way of doing things and into vibe coding?

Z: Yeah, that’s definitely a lot of challenge and work. So I actually proposed it back in October last year, to our design managers, to design leadership. I said, “Let’s get our UX designers out of Figma.” Of course, everyone was like, “No freaking way. You are crazy. Designers are in Figma, that’s our tool,” and everything.

But the reason I proposed it is that it wasn’t just a random proposal, like let’s get rid of tools or anything. At the time, we had a new design system that was entirely in code, and we were fortunate in a way, because instead of trying to continue building multiple design systems and trying to move them along, to modernize all those design systems, from the top down there was a mandate. This is the design system we’re going to use. That design system is in code.

And that’s really what prompted this proposal. That didn’t happen, so by the time I talked with Peter, that was already three months after. I think we talked at the end of last year, and it was October when I was proposing it.

But by then, just de facto, no push or anything, designers were already out of it. But there was a lot of conversation. If I could have done this all over again, I would do it differently. I would be reaching out to the engineering team immediately and talking about this transformation. At the time, this just organically happened, and then by the time I talked to Peter, this is… That’s when we started to realize, oh gosh, we need to talk to engineering a lot more. Some engineering teams still required our designers to give them a Figma file. Some other teams were more open, and you could do other ways of prototyping. And there was a lot of discussion about what designers were doing in code, and we also had to go out and talk about it.

There are different levels of designers in code. So there’s the- One, the basic thing about getting designers into code is engineering empathy, right? So engineers now, instead of just coding, they do a lot of reviewing code as well. So what it takes to- for an engineer to build something, that’s something designers should understand as well.

And then another level is where we got our team to prototype, but then by the time February this year came around, our designers were actually shipping production-level code. It sounds so grand, production-level code or whatever, right? But by then we had worked with the engineering team, put a lot of guardrails in place, about what designers should not be touching in terms of code. If it’s an API, if it’s infrastructure, if it’s, say, if it touches a flow, these are things designers should not be doing.

And what we’re actually talking about when we say shipping production-level code is paper-cut-level shipping of code, right? So change a piece of copy, change a wrong component, small changes.

And so these are things people sometimes talk about, “Oh, designers shipping code.” They put it under a blanket umbrella that says, “Designers shipping code.” But there are actually really different levels of designers even touching code. People are not getting there because, “Oh, designers shipping code. Are we turning designers into engineers?” No, absolutely not, right?

So same thing, we opened up Figma for other cross-functional teams to use. PMs using it, engineers using it. Are we turning engineers into designers? Probably not. Are we turning PMs into designers? No. But we’re turning everyone into a product builder, a contributor, in a way they’re passionate about, wherever they see a fit with the tool.

Now we’re basically just giving everyone all the tools, not just keeping Git for engineering, Figma for design, or whatever the PM tooling is, but we’re actually giving the entire tool stack to everyone who is touching product and building, and they use the same tools we have. And so that’s where it is. But it takes a lot of talking, coordination, and it really does hit some nerves because everyone is jumpy, and designers say, “Oh gosh, engineers designing, PMs designing,” and the engineers say, “Oh gosh, designers coding, PMs coding.”

So I wouldn’t say it was all smooth, but at least that’s something we put a lot of effort into, and we saw results from doing that.

Jesse: One aspect of your story that I think really resonates with what I’m hearing more and more, and what I’m seeing in AI transformation efforts broadly, is the notion that you have to meet people where they are inside the organization. And imposing a kind of one-size-fits-all policy for this technology is not actually going to get you there, that you need to be able to find ways to leverage potentially a broad range of different skills across your team in a way that you haven’t before, and to be able to accommodate a diverse range of different kinds of workflows, and setting different kinds of expectations accordingly, cross-functionally, with how product and engineering interface with and interact with design.

I wonder for you as an ops leader where your mind goes when you think about managing operations across a diverse, distributed set of work processes that no longer fall in line with a single paradigm anymore?

Z: Absolutely. So I come from a very strong operator’s perspective, right? So in the past, as operators, you were the process wranglers, basically. That’s what it is. You want to… The word we used for the longest time was standardization. Standardize the process, and that will actually scale, right?

So but right now we’re pitting speed versus quality. There are a lot of discussions in there, whatever. Like you just said, standardizing everything won’t work anymore because different teams move at different speeds, and different teams have probably started to adopt slightly different workflows. And some teams might… Some companies, some teams, might even allow them to use slightly different tools or whatever.

So I wrote about it, and to talk about it now from an operator’s perspective, I push a lot for shared principles, and then giving people the agency to work out the details, how to execute it, and to have a little more flexibility instead of standardizing across the board.

But shared principles are something every team needs to spend a lot of time aligning on, and also educating everyone and talking about, because if you think about shared principles, for designers, there are certain things, right?

Accessibility is a, for us, something we care a lot about, and engineers care about that as well. And engineers probably care a lot about their code quality as well. So their APIs, nobody touches, and as long as we’re clear about what everyone can contribute and that everyone should reach out to the experts to contribute, that helps the team move in different formations, but still moving in the same direction.

Peter: I’m, so, I’m gonna continue on this thread because when we spoke about this at that Figma meetup, the light bulb that went off for me is that this type of AI transformation might be better led by operations folks than design leaders.

Whereas my kind of working assumption in the conversations I’d been having with clients and whatnot, design leadership was responsible for that. And, if they had an operations person, maybe would be leaning on them to help.

But something that’s also happened over the last couple years is a lot of ops teams have evaporated. And so the, the irony being we’re in now in this moment that is so operationally heavy, and many teams don’t have operations folks to help them through it.

And I’m wondering what is your relationship with design leadership through this type of experience? What are you responsible for? What are they still responsible for? How do you distribute authority? Who’s making what decisions? That kind of thing.

Z: Yeah. So if you think about design operations in general, with your leader, it’s always a balance. It is always challenging to divide that responsibility and accountability. It’s just because different teams work slightly differently.

So in my specific situation, it worked out really well because at the time, I reported to the head of design, and her mandate from the top down was AI transformation. And then my part of the work was actually getting that done.

And then the design leader coming in down to the team, this AI transformation, you think about it as a gr- grassroots effort. Everyone wants to use something, build something.

But to do it right, you absolutely need top-down support, to give people the time to do it and to give people the direction, where to go and what we want them to do. Do we want them to stop at prototyping? Do we want them to ship code? We do need to know what the end stage is that we need to get the team to.

And as an operator, then we can actually help the team achieve that and figure out the logistics, scaffolding the team step by step, how do we get there, get the designers into code.

I came from a very technical company. It’s extremely hard to get into our production code base, rightfully, and it should be. It shouldn’t be turnkey, where everyone can ship code. So there’s a lot of coordination. It’s my role and my team’s role to go out, reach out to our engineering partners, “Come on in, help us do it right, because you do want us to do it right. You don’t want to review crappy code. You want to teach us to do the right thing.”

And then so in return it helps them as well. And also a lot of explanation as well, “Hey, we’re not trying to be engineers. We’re actually trying to take care of the design debt that engineers never have the bandwidth to take care of, and they are very small paper-cut things.”

So my goal is really to focus on the how. How do we get the team there? But design leadership is the what. Coming in with the what, and giving the team the mandate. That’s really important.

With these things, if you just say, “whoever wants to get on the bandwagon, let’s do it,” it is really hard to move that fleet in the same direction. Those would just be sailboats, right? Everyone’s like, “I want to go. I want to go really fast. I want to do something.” And then someone else wants to do something else. “I want to use this tool.” “I want to use that tool.”

So the design leader needs to come in and say, “This is where we’re going to get people,” the what, and then the operators come in with, how do we get there?

And that worked out really well. And then also because we’re… We say it’s design operations, but on the other hand, nowadays my perspective on operations is that maybe we’re not design operations, we’re just operations, in a way. Experience operations, whatever. Reaching out to more teams outside the design team.

And after our transformation for the design team, I ended up going out, because of our training, we had everything in place, documentation, recordings, process, all the things in place.

Now other teams, these non-technical teams, came to ask us and say, “Can you train our team? Can you train our team?” So our team members, our operators, actually went out and thought more about how to leverage our knowledge to up-level the cross-functional, cross-board, company-wide AI transformation, everything.

So I’m thinking and trying to figure out, do we still use this term design operations, and does it still have a meaning? There might be, but there might be more. Maybe design operations needs to be more of just a higher-level operation. Experience operations.

Peter: I like the phrasing of experience operations. I’m, I’ve always had issue with the phrase design-led. A lot of companies, 10, 15 years ago were gonna be like, “Let’s be design led.” And that always, even as a design executive, that made me uncomfortable because it was elevating one function over the others.

I don’t want to be engineering led, I don’t want to be product led, I don’t want to be design led. Those are disciplines. N-no discipline should lead. I have always actually liked “experience-led” ’cause that’s an outcome. How are we all working together to achieve an outcome? And so this idea of experience operations resonates well with me.

But I’m curious, we might be getting a bit in the weeds here, but let’s go on that journey. How did your experience in design operations change? Because…

So when I think of design operations, I see two pillars to it. There’s the team operations pillar, right? The internally oriented pillar, career frameworks, and recruiting, hiring practices, and culture stuff that’s really specific to design.

But there’s also always been this program management pillar. When we wrote Org Design for Design Orgs and we wrote about design operations, it was pr- mostly around program management, which was how do designers work with other functions to deliver better experiences, to get back to that word.

And I’m wondering, did, has there been an, a meaningful change in design program management? I understood that role to already have a cross-functional mandate and set of relationships. Maybe I was either wrong and primarily, at least in, in your experience, DPMs were still primarily internally focused, just helping designers do their work.

Or maybe I was right, but there’s still something interestingly different about what it means to be a design program manager in a pre-AI world and now in a, I wouldn’t call it post-AI, but as we’re moving through this transformation.

Z: And AI transformation. Yeah, so I wouldn’t say it’s wrong, but also it was right for the time. What– And also it’s a different perspective.

You’re looking at practically how to structure our organization, right? But if I think about it, I like how this is also… I didn’t invent it, you know, that we sometimes frame design operations as a focus on how we work together, how we get work done, how we articulate impact.

And so if we look from that perspective, then it doesn’t really have to be divided into a people program and a DPM program. It doesn’t have to develop that way.

Say, on our team at the time, I had a small team. I had people focused more on people, and I had people focused a little bit more on maybe just research operations or something like that.

But then they don’t have to be in that vertical anymore. They can come out to help the operator, the operations team, think about how we work together. That’s how we’re changing our tools, changing our ways, changing our process, changing our workflow, all that.

And how we get work done, that’s where we can actually do more of the training, teach people, scaffold people to get these things, to use the new workflow, to use all the new tools.

How we articulate impact, that’s when we transform our team using the new way of working with AI tools. What did we do? And how does that move the needle, how does that impact the customer’s experience? Is it because we’re fixing a bunch of the paper cuts, the retention is better, the call tickets, the, the customer support tickets go down, whatever.

We haven’t gotten that far, but that’s where the measurement will be, how do we articulate impact. So then we don’t have to separate the organization so specifically, that as a TPM, you can only help the program. But as a TPM, you can, oh, or as a DPM, TM, whatever, you can come out and help the transformation as well.

So that’s how I see it.

Jesse: One of the things that I think makes ops such an interesting leverage point for AI transformation is the holistic view that you have, in a way that even design leadership, they can only kind of– they can only see in certain corners at certain depths and so forth.

And this, as a process, it’s become increasingly clear that this is a process of learning as you go, that that every organization has to take this journey of taking stock of themselves and more deeply understanding what’s going on with their processes than maybe they ever have had to do before.

And I think about the feedback loop that is required to keep an AI strategy on track, right? You need to be able to do all the things that you’re saying about get the tools in people’s hands, get the knowledge in people’s hands, continue to educate, bang the drum for the right principles, et cetera.

And then you have to figure out what worked, to your point about articulating impact. But there’s a thing in the middle there which has to do with just taking stock of all of your experiments and understanding where those experiments are going and how that’s actually adding up to something.

So there is almost a a kind of a grassroots strategy element required here, where I’m imagining that you’re the one who is really setting the criteria by which things get bubbled up to the leadership and things become, new ideas become strategic recommendations.

Z: And ideally, yes. And in the past, a lot of that was reactive, right? Because it’s so new. Our– At the time, the org I worked for was pretty much on the far end. We weren’t an AI-native company building AI, but we were pretty close, one step behind, right?

And one thing is that you have to… I almost think you have to let it be a little chaotic first and then see where things land, and then try to rein them in to figure out how we can actually organize the buckets and everything.

So at first, the biggest challenge, again, back in October last year or whatever, was the fear. A lot of the discussion back then, if you think about it, was that it’s replacing our jobs. Are we actually going to, because of that, right? So that was the biggest d- discussion in October.

And the majority of people… I know, Peter, you just did a survey, everything. A lot of people now are moving to… If you look at a bell curve, they’re moving to the middle now. Actually, you see the whole industry is moving just from October to now. But if we were to do a benchmark back in October, the majority of people were in that, “Oh, stay back and let’s see what happens,” and I’m a little afraid, stage.

So when that happens, the biggest challenge for us is to get over that hurdle. So the way that we started was actually letting people just build whatever the heck they want, really, and just build, and then we’ll deal with it. And so we had… The first thing, we didn’t even talk about prototyping or anything, just build.

You can vibe code. And designers loved it because, “Oh, I have a problem. I could never get an engineer to build it. I’ll build something for myself.” And then so we did it, and everyone built that… I did a, a series of vibe-coding trainings. And then in four months, we had 30-some apps spin up within our team. Given that we were a 40-person team at the time, right?

And it was a little bit Wild West, and then people started to find out, oh, we’re building similar things. We’re building contradictory things, maybe, to what other people are building.

And but that’s good, actually, because then we see that, and then we start to think about what’s actually worth building upstream and everything.

And so I think it has two sides, grassroots, and also you need to let it grow a little bit and then see where it lands, and then start to put in some kind of principles to get people back together to keep moving. And I don’t know, I, I just started with a new team, whatever. But that’s the learning I’ve taken, and then go to- getting to a new team and they say, “Okay,” so I start to see we’re definitely far over that curve now, so people are not in that reluctant stage anymore.

Everyone’s getting a little bit more towards the accepting side of everything. But I still see the same thing. Everyone’s building. Everyone’s building their own, and there are really amazing tools now, some really good tools. However, these tools still don’t talk to each other, and there’s no really good function to govern any of these tools that get built, that every individual builds.

And yeah, so that’s a new challenge for me right now.

Peter: I wanna rewind a bit and get back to the conversation we had. Something that you wrote about on, in your newsletter that I drew from based on your experience doing the kind of AI transformation work, was on people’s relationship to their roles and who does what in a team.

And I’m bringing this up because I was just in a conversation… Oh, with one of my clients. I, one of my thought partnership clients, and they’re actually going through… It’s funny. They’re go- They’re not even going through the AI transformation yet. They’re going through a simple product operating model transformation. They are that far behind that they’re only now adopting things like product discovery, and how do we work three in a box, and what does it mean to have a product designer as opposed to a separate UX designer and UI designer?

So that’s where they’re at. But obviously, they’re going through this transformation during a time of AI, so there’s going to be a lot of turbulence. And the question they asked me, and I’m… want to ask you, is around roles and role definition and who’s doing design and how many people are doing design.

And let’s say not just design. Design, research, content, that full suite of kind of classic UX practices. And what you witnessed in terms of how practice is done, who’s doing… what’s worth maintaining, if anything, and what’s worth throwing out and trying something new. What was… What have you seen in, in this shift?

Z: That’s a loaded question, isn’t it? To me, and this could be a very radical perspective, and I’m always a little bit on that edge. So to me, the only thing really worth preserving is the agency for people to do what they love to do, and the role specifically, and it could be design, could be engineering, could be PM, the traditional EPD model, and those are just labels.

And so people have their passions. I’m more passionate about designing and about… I also code. I love coding and all that, right? I want to see if there is a way that, instead of thinking, everyone has expertise, but they don’t have to be labeled as a designer, an engineer, or a PM, and their expertise is customer-focused experience.

Their focus can be something like that. And I want to see a world where people have more agency to assemble organically. And so it doesn’t have to be strictly a proportional EPD ratio. You’ve got one designer, one PM, two engineers to build something. What if I have a designer who is an excellent coder, so I could have a design coder, a design engineer, work with the PM on it?

Or it could be something like, I have an engineer, I have, some engineers have an excellent design eye, but their passion is coding, so they can actually lead that maybe with the PM. And then we also have a lot of designers who have excellent business sense. They have been founders, they have run their own agencies, they understand the business so well.

But maybe it’s a designer and engineer formation, so I want to see that organically formed, whatever you call it, squad, po- pod, whatever, to actually focus on the product to build. And but everyone still has expertise. So if I go in with the engineering team, I don’t even try to pretend I’m, that I can code, engineer, anything, but I understand where they’re coming from.

That’s why I see the AI era as excellent, because it gives people certain abilities that they didn’t have before. They always wanted to do it. Maybe there was no time, maybe it wasn’t their top passion or anything. And now designers can come in, do a prototype, code something, and then do it, and then maybe if we train everyone right, maybe that code is good enough to even… for engineers to just take it, polish it up, and then ship it and everything.

We talk a lot about AI-native companies, and they’re shipping so fast. Designers’ code, a lot of the time, gets into the engineering product anyway. I’m less precious about labeling.

And I am a designer. If you ask me, I’ll say, “Okay, I’m rooted as a designer,” or I put that down as my passion. I am always biased towards the design team. That’s my root and everything.

But where I came from, I also saw a lot of the engineering perspective and everything. I worked for a company way back. We did a lot of pairing. I would sit down with my engineer every Friday, just watch them code and everything. So I want to see that more organic way.

And I know that there are a lot of people who said, “No way. How can you take out the discipline, the designer discipline?” And that’s been their whole identity for the past couple of decades and everything. But for me, myself, it’s not… I’m not that precious about that particular label, but I’m more precious about what I’m passionate about, what I can do, and I’m an operator now.

I can label myself an operator, but I’m also a builder. I also could be a strategist or whatever. I’m working on the strategy level or whatever, but it’s about capability.

Jesse: Peter and I once ran a company where we didn’t believe in titles and role definition and things like that, and we basically treated our entire group of consultants as a kind of one category in our systems. One thing that came out of that experience was that it made things like performance reviews really challenging because it made it a lot harder to make apples to apples comparisons against some sort of rubric, against some sort of standard of performance or quality.

So everybody’s performance review ended up being tailored to their bespoke set of strengths and accomplishments, and I wonder about the scalability of that. Ob- obviously there’s more than one way to approach this kind of a situation, but I think the, the challenge still remains of having just way too many distinct ways of doing things in order to be able to, again, evaluate what’s even working effectively anymore.

And I wonder how you scale that.

Z: I wish I had it o-on hand. So I was heavily influenced by Corporate Rebels, their way of thinking about a very progressive organization. And then part of the thing is talking about this flat organization style, whatever, right? So you think about designers or engineers or PMs, if you put them all in one bucket, how do we really evaluate performance and everything?

Because what we’ve been trying to label as the craft or whatever, that is one thing we’re being evaluated on, right? So that’s a thing. But it could potentially be more two-dimensional, right? So everyone, you have your strengths, that craft, what… It’s your strengths, whatever, and then you can be evaluated against that.

But there are just other dimensions, how you work with other people, how you push product, how you impact the business, and all the other dimensions. Everyone’s the same. I’m contributing from a design perspective. You might be contributing from an engineering, more engineering, perspective, whatever.

And so we have that little sliver. And then, but the other dimension is everything else, how we actually move the product forward, it could be.

And I don’t think you have one size fits all, but that’s why I’m interested in the organ- in the more progressive organization style to think about.

The team can decide. My pod can decide this is how we’re going to… This is our goal, and this is how we’re going to evaluate at the end, do we, how do we achieve that goal? And the team can decide a little bit. But of course, from a larger organization, you’ve got to think about, again, you’ve got to set the team goal, and then the team can actually organically evaluate themselves in order to reach it.

And it’s hard. I think I wrote that this is the best time for ICs to build stuff. Excellent. This is the hardest time for leaders to lead because it’s really hard to figure out the how now, because there are so many different ways. But I think the most important thing, I don’t remember who talked about this, is that as a leader, you’re the commander of a fleet of battleships. You’re not a commander of little sailboats. So if you let the team build as sailboats, then it’s super challenging. However, if you can run the team as a commander leading a fleet of battleships going in the same direction, they’ll have a better chance of getting everyone moving in the same direction.

But each battleship, they… Their own commander has a lot of decision-making agency.

Peter: So many thoughts.

Z: Yeah.

Peter: This, this role conversation and how roles are defined, touches on identity. You mentioned that earlier, right? I am a designer. I went to a design school. I have had the title… I’ve had the word designer in my job title for 15 years. That defines me.

And so I’m curious, so that’s one thing, though. Like, how have you handled the soft, squishy, human kind of aspect of this and helped people through that?

Jesse and I, a year and a half, almost two years ago now it feels like, but at least a year and a half ago, when we first started talking about the phase shift, one of the things, one of the themes was ego death, right?

We’re gonna have to let go of our identities as whatever, designers, because it’s getting in the way of our ability to have impact.

But 18 months later or whatever, people are still attached to those identities.

I’m curious. I’ll limit myself to two questions. I’ve got five, but I’m gonna limit myself to two questions.

I’m curious how you’ve helped people navigate that identity shift, but then, and it’s related how do you recruit and hire, right? What is the title on the job posting when a designer could also be a developer or p- maybe a PM, or it’s one flavor of designer versus another or whatever, right?

One of the benefits of clearly defined roles is you can signal, ” Hey, we need to hire someone with this set of skills,” and this title equals that set of skills. Now, though, when titles and skills are becoming decoupled to some degree, or at least not as tightly bound there’s a very practical challenge of how do I recruit and hire.

So on one side, how are you… how have you brought people along throughout that identity challenge? And on the other side, how are you making sure that the people you’re bringing in are the right folks for the work to be done?

Z: Yeah. So let’s talk about the recruiting side first, because that’s the Wild West right now. You can go out and do a search. There are a lot of designer-labeled jobs, sure, but you also see a lot of companies that start with things like member of technical staff, whatever those labels are, right?

And then you have people s- tell… putting out titles I have no clue about now. So it’s challenging for people to look for a job, it’s challenging for companies to hire, and it is really challenging right now, but that is also the Wild West right now.

We are eventually going to figure it out. Honestly, I think for operators, I’m a little bit used to this scene, because for the longest time, design operations had no title, and there were all kinds of descriptions and then trying to figure out what it is. We’re finally just about to have some kind of titles, DPM, design operations, research, finally.

But now that I’m talking about, let’s move this out of order. Let’s talk about other capabilities, right? So I’m a little bit used to this. It is challenging, I have to admit, and a lot of the time even the job description is very challenging. People are going to just throw… It’s a kitchen sink. You gotta be this, you gotta be a designer, you gotta be able to code, you gotta understand design systems, you gotta lead, do strategy, and all these kinds of things. It is a kitchen sink sometimes because they don’t want to forget something, because they don’t know what they really want.

So that being said. But hopefully when people come in to interview, it’s also challenging when people come in to interview if the company doesn’t know what they want and then they go back and forth, it’s super, super draining for the people who are interviewing as well. So these are definitely… I’m not gonna get in depth about the hiring side of the problem.

There are a lot of discussions out there, but the thing is, I talk to the designers. You can still call yourself a designer, you can still call yourself a builder, however you want to call yourself. What is super important on the talent side is that you’ve got to be extremely clear about what you want to be, and then go talk to the company and find out if that’s what they’re really hiring for.

And when I look for jobs, I always look at three things. Whether the company’s values align, the company’s values, that’s like don’t be evil, right? So basic things, that’s something I care a lot about. Another thing is c- about the people on the team and the work that you’re doing. And then another thing is also trying to think about the technology side I want.

I want to be a little bit on the cutting-edge side of the technology. So that frames how I go look for a job. I can look for jobs in design strategy, design operations, business opera- whatever the title, I don’t know, but I’m super clear about what I want. So hopefully designers can form that, I want to work for A, B, C, and then go look for that job, on both sides, to help the company also form a little bit of what they’re hiring for.

And I get it. I really, I personally don’t care about titles, but I’ve been around for a long time, and for entry-level job seekers and everything, titles matter, whatever, right? So take whatever you’re happy with and then go with it. You can redefine it or not, or start to build on top of it, whatever.

And then, but I think, again, I’m always on the side that I care less about the labeling and more about the substance of what it actually is. So…

Peter: You and I care about that, but we’re weirdos.

Z: I agree. I agree. I am. So it… But that helped me and the—helped me a lot in looking for what kind of job I want. I always go into every… So far in the past three jobs I’ve had, I always go in looking for what that job is. Eventually we figure out whatever the title, you can call yourself whatever, right? So it’s figuring out that title.

But I care a lot more about the job I’m going into. And that helped me find jobs as well, because I’m super clear. I’m not… if you ask me, “Oh, what do you want?” And everything is like, “Oh, whatever you have, I will do it,” you will never get anywhere. So I’m super clear. This is what I want to do. Are we aligned?

It’s a, it’s like a marriage. You gotta be a match, right? So I want to match with my job. So this is what I want. Is that… We can go back and forth a little bit, but overall, do we match? If it’s a match, then we go forward, right? But that’s the hiring side. And then talking about how do we talk to the designers right now, right?

So most likely nobody’s gonna change the titles, changing them for the companies that have been around, say all of a sudden we’re gonna change the entire design org to staff of the tech- technical staff or member of technical staff or some… Not likely. But so the deal is, again, caring more about their capability, and you’re a designer, your expertise is customer experience if you’re a UX designer, right?

Your cu- your expertise might be customer experience, everything. But then also what else that designer has actually been really interested in. Some of our designers are more interested in the business perspective, so they actually transitioned themselves into a designer PM, whatever you call them, but they’re actually leading the product and everything.

And so some other designers might be more interested in the technical things. They’re moving to the… So design engineer is even a traditional title, right? It’s been around for a long time. However, they’re moving more towards the design engineer side. So I know I…

You two talked a lot about the design engineer or the strategist. These two ends are taken care of. It’s all the people in the middle. It’s a little bit harder to focus on. But the thing is that these are the people we can actually start to help understand where they want to be. And there might be even new possibilities. Instead of a design PM, a design engineer, could that be a design salesperson?

I don’t know. Go-to-market designer or s- I don’t know. And but it’s, again, going back to that organically formed idea. If this product needs something, can I be the right fit to push that? And I’m still a designer, but what I do might change slightly now.

Jesse: I notice that what that asks of the leader on sitting on the hiring side is for them to be, as you put it, much more aware of their own needs, but also to really take on the role of intentional curator of a team, and not just hiring resources because they fit in a box, but rather to be evaluating them.

Like you talked about looking at it as a two-dimensional problem. That it’s not just about craft and skill, but it’s also about organizational compatibility, collaboration, working together and how effectively they can do that. And the conclusion that I’m drawing from this is if I’m a manager, a leader engaged in an active hiring process, I need to be paying a lot more attention to that second dimension of how people work together and form trusting relationships than I’ve ever had to before really.

Z: That’s why design leaders benefit from operations support, because we are always looking at these things, right? So as operators, we’re always looking at the capabilities, how things work together, how do we scale things, how do we move everything together, and as a partner.

Jesse: That touches on something interesting that you said in your newsletter a while back that, that struck me, in which you compared design operations to the practice of service design. And I wonder if you can expand on that idea a little bit. What do you mean by that?

Z: So my thinking has also expanded a lot compared to when I wrote about it. So a lot of the time I say I’m biased, I believe operations is extremely valuable, important, and all that. And also, in reality, I know it’s also a, a luxury a lot of the time for a lot of teams, everything. But I am rooted as a designer, and coming from a service design perspective, maybe not UI.

I was trained as more of a graphic designer, but then evolved into all different things. I had my own business for a long time. And so I really evolved myself into looking at these things. What is the problem at hand, right? So when we started as a design operations discipline, we were trying to solve a problem, a challenge the design team had back then, right?

So that’s how this whole discipline started to form, to become a label and everything. Essentially, we were service designers to the design team at the time, right? So that’s more of our perspective. So w- we are looking at a service design approach to what is the challenge or what’s the problem on ha- on hand for the design leaders.

How can we come in to help the team solve these challenges and everything? That’s exactly service design, and it’s just service design for the design team. But now I even see it more as service design for the product or the org and everything. I’m trying to push really hard to start to lose that design operations label and to be more of an experience operations.

And I think that’s really important. And for us to think about what is the problem at hand now. It’s not… Now, especially with all the AI transformation, it’s no longer just the design team’s problem anymore. Everything the design team does will touch everything else now. And then with AI, it just comes faster.

And then you don’t have that luxury to think, I can go through a double diamond for a year and then figure something out. For many tech companies. So you’ve got to think about, when you move as a team, how that ripples out to all the different teams, everything. And I think the operator, the experience operator, is the best person to see that bigger picture and to service that service.

Peter: It’s a, it’s an analogy or a an alignment that I’ve also seen and experienced as someone who, when I was a more n- normal designer, I was more of a service, I was more of a service designer, right? At Adaptive Path, we were doing, we called it UX, but we realized pretty early on that our UX design approach was a service design approach.

We were looking at the broader organ- organizational systems of the, our clients and in order to better understand their ability to deliver these experiences, right? And so that required a service design mindset. And then when I became an executive and I needed to start thinking about shaping my team. Two things.

One, I would adopt a service design mindset in terms of thinking about, like, how do I, how can I use a journey model to organize design? ‘Cause I think that is m- more responsive to the needs of our users. But then to your point, when you start getting into a systems mindset, you’re looking at your team as an organism and how do you operate effectively?

And this kind of starts to dovetail to something you’ve been writing about more recently, which is the relationship between operations, and I’m gonna continue to use your term experience operations, to the relationship between experience operations and quality. One of the biggest concerns that you hear from designers is that because of speed, because of ease of access, more stuff is being made and it’s broadly mediocre.

This is borne out in research, Figma’s research, Lenny’s research. They’re like, “Yes, people are going faster, but no one is happy with actually the quality of what is being produced.” Everyone feels supercharged, but then when they reflect on what they’ve made, everyone’s “Eh, this is crappy.” Or it’s not bad necessarily, but it’s it’s not getting any better.

I’m curious, you’ve been writing about this a bunch, so I, I’m not gonna ask you to repeat everything that you’ve written. But as you think about this responsibility, maybe that experience operations has in helping establish quality bars, quality rubrics, w- how do you approach that?

What do you make of it? Yeah.

Z: So speed and quality, a lot of the time we see them at two ends of that spectrum. But I don’t like to see it that way, actually. And part of things that… Ask a designer, “Do you care about the quality of the product?” Not just the design, just the product.

The answer is 100%, absolutely, right? So you go ask any CEO, “Do you care about the quality of your product?” You’re getting 100% the answer, “Absolutely. I care about the customer, I care about their experience, and of course, I care about the profit and the business as well, but I also care about the business and the quality of the product.”

So that’s actually aligned. As an engineer, do you care about the product? They care from the code perspective, about the product and everything. Everyone cares. So if I, as a designer, go out and say, “Hey, engineer, you just shipped something. This looks so crappy. It’s bad quality and design.” Is it true? Yes. But have we ever articulated to the engineer what is good? We probably never actually spent that time to go out and tell the engineer, “This is why we care, and this is what is not quite right, why it matters.” We never spent that time.

Peter: I know it while, when I feel it, Z. I, I it’s… I just feel it.

Z: Okay, so how do you feel it, why do you feel it that way, and is it because the color is wrong? Is it because the experience is jarring? Is it… I can ask you that, right? So it’s teaching people that you feel it, and how you feel it, and why you feel it, and that’s important, I think.

And same thing, an engineer can teach us about code, why my code is crappy code, they can tell me, right? So I will learn in that process and everything.

I also wrote a lot pushing on this, sp- speed is really not the enemy, but it’s really for us, if we can, not hold this design craft just to ourselves as a moat, but really think about it. The best thing is, 20 years ago, fewer businesses were talking about design thinking, and now you think about business, they understand, at least they understand the idea of design thinking, understand that focusing on the customer results in good business or whatever.

At least that is actually progress. We might say, oh, we’re rolling back or everything, but it’s a spiral. We’re actually moving towards a better position. So I talk about how I want to see design maybe as a discipline eventually dissolve or everything, but design thinking become more of a human nature. Everyone, whether you’re a PM, whether you’re a designer, whether you’re an engineer, business, or sales, you’ll care about this design thinking approach at least.

So that also, I think a designer… Now it’s the best time for designers because we understand, we can deal with ambiguity, and we understand the design thinking approach, we understand the customer, and if we can learn more, I think for designers to understand the business and everything, this is the best time for designers.

Peter: Let me just do a quick follow-up. My question might, is quick. Z’s answer might be long. So we need to articulate standards of quality. We have to go beyond feeling to what leads to that feeling. What is the role of experience operations in that conversation?

Z: Build in layers of quality control. One, what can be automated, what has to have a human involved? So from an operator’s perspective, and right now in my- in my new role I’m working closely with the folks who are talking about QA and everything, I ask a lot about what can actually be built into the system so that it makes, creates a condition where doing good design is actually easier than doing bad design.

And for non-designers, that’s one, from an operator’s per- perspective. Another thing is that if this layer didn’t catch all that, then that needs to come to the human, and then we designers can come in to do the human check, can do the human education to talk about it and everything. So that’s the operations perspective, to build this system to make doing good design easier than doing bad design.

Jesse: So as that perspective continues to evolve with new technology, I’m curious about what for you is the biggest unanswered question that you’re curious about the future of your own practices in design or experience operations?

Z: I, again, do not hold this particular label or anything that dear to my heart, in a way. I’m passionate about it, but on the other hand, if you look at my career trajectory, it’s always different, slightly different. It’s not a straight line. And I think all that experience coming in helped make me how I operate these days.

And so what I’m curious about is really, I honestly think this is the best time. AI gave us a lot of capability and everything, but right now we’re actually stuck in this language model. And I’m looking forward to seeing a spatial model and everything, other kinds of AI.

And I want to see all these new technologies, how that eventually will actually impact humans and human progress, and it doesn’t have to be about being an operator anymore, it’s just more the grand scheme of life, right? So how that can really absolutely enhance our experience to be more human and to do the– to make those decisions only humans can make, and come up with those ideas that actually progress the human race and everything.

I’m looking forward to that, and I’m curious where that goes, because I truly don’t believe we are going to be s- stuck with just language models forever.

Jesse: Z, thank you so much for being with us.

Z: Of course. Glad to be here.

Jesse: Where can people find you on the internet if they wanna learn more about you and your thinking?

Z: LinkedIn is the best place to find me, to get in touch at a high level, and I write a lot d- on my Substack and everything, so we can share the links. And those are the two places to find me easily.

Peter: Got it .

Jesse: All right, fantastic. Thank you so much.

Peter: Yes. Thank you.

Z: Thank you for having me.

Jesse: For more Finding Our Way, visit findingourway.design for past episodes and transcripts, or follow the show on LinkedIn. Visit petermerholz.com to find Peter’s newsletter, The Merholz Agenda, as well as Design Org Dimensions featuring his latest thinking and the actual tools he uses with clients.

If you’re looking for help with AI transformation or you just need a private advisor to help you solve your hardest leadership problems, visit my website at jessejamesgarrett.com to book your free one hour consultation.

If you’ve found value in something you’ve heard today, we hope you’ll pass this episode along to someone else who can use it. Thanks for everything you do for others, and thanks so much for listening.

In this episode, Peter and Jesse compare notes from Config, Figma’s AI study, Lenny’s newsletter survey, and countless conversations to read the current state of design leadership. The signals: existential AI panic has cooled into exhaustion, organizational chaos and leadership churn are the new normal, and design still stumbles on business acumen. Their case for thriving—lead, don’t just design, and reclaim design’s unfinished mandate.

For more from Jesse James Garrett, including his AI transformation practice: https://jessejamesgarrett.com/

For more from Peter Merholz, including his newsletter, his consulting, and thought partnership: https://petermerholz.com/

Jesse: I’m Jesse James Garrett,

Peter: and I’m Peter Merholz.

Jesse: And we’re finding our way,

Peter: navigating the opportunities

Jesse: and challenges

Peter: of design and design leadership.

Jesse: On today’s show, Peter and I are listening to signals of the current state of design leadership. We’ll get into what we heard in our recent conversations with design leaders at events such as Config in San Francisco, and what recent research studies from Figma and Lenny’s newsletter reveal about the emotional toll of the current environment on leaders and teams.

Plus, we’ll explore what leaders can do to keep the promise of design’s value alive with the rise of AI.

Peter: I wanna start with this question.

Jesse: Okay

Peter: Have you seen the movie Backrooms?

Jesse: I have not seen the movie Backrooms, Peter.

Peter: I finally saw it four or five weeks after it was released, and it is easily the most interesting thing happening in cinema right now. Full stop, end of story. If you like movies, you need to see Backrooms. If you think it’s a horror movie, it’s not. If you don’t like horror movies, don’t worry about it.

Go see Backrooms.

Jesse: Okay. All right, thanks

Peter: I haven’t walked out of a movie kind of excited about the form in a very long

Jesse: Cinema yeah.

Peter: In cinema. No, for real. But what’s on your mind, Jesse?

Jesse: Well, you know You know, here on this podcast, Peter and I, we’re like the great psychologist Fraser Crane. We’re always listening. And we’ve been listening a lot over the last six, eight weeks, since the last time we recorded this podcast.

We’ve been listening to the signals out there. We’ve been having conversations with folks. We’ve been together at a couple of events. We’ve been taking in what’s going on, and there’s enough going on out there that I thought it would be worth us getting together and talking about our reactions to some of the signals that we’ve been seeing out there.

So, for example, you and I were at Config, the largest design event in the world now, it’s gotta be, in San Francisco just a couple of weeks ago in June. Had a chance to talk with a lot of different design leaders about their challenges and about what they were seeing, and of course, all of us were trying to read the tea leaves of Figma’s product strategy and what that meant for design teams and what they were maybe seeing about where all of this is going.

They published the results of their latest survey of design practitioners and design leaders about the state of AI in their practices and had some interesting insights and reflections based on that.

Jesse: But I’m curious about what stood out for you. Let’s just start with Config. I mean, there’s been a bunch going on, but let’s just start with Config. What stood out for you about the conversations that we had and the experiences and the ideas that were in play in that gigantic gathering of 10,000 designers in San Francisco?

Peter: What stood out from Config specifically for me was that AI was no longer seemingly an existential concern for design and design leaders the way it had been in the prior two Configs.

It was two Configs ago when Figma was like, “We’re about product people,” and didn’t really mention design much. And designers started freaking out that they were about to be replaced by AI. I mean, yeah, so that was

Jesse: Or simply product managers.

Peter: Or product managers…

Jesse: You decide which fate is worse.

Peter: Sure. And then in 2025, Figma said, “Psych, we love design. Design is great. Here’s a bunch of tools for designers,” and that’s when they launched Figma Make as well.

But the conversations I had last year were deeply existential, It was around that time last year that you and I started really hammering away on the kind of liminal concepts and the phase shift concepts and all that kind of stuff coming out of this dialogue that was occurring.

This year it feels like folks have settled in. This AI stuff is real. They’re still figuring out what to make of it, but it’s real. It’s not going away, but it’s also not causing the kind of existential crisis it had before. It’s a tool. It’s a means to do their work.

And yeah, so folks were far less hair on fire than they had been the prior two years.

But what’s replaced that or what, has emerged, I think, as the dominant sentiment is they’re just tired. Everybody is fucking tired. Everybody is exhausted.

I think a big reason they’re tired is that all this new stuff has simply been layered on top of whatever their existing job had been. And so folks are just expected to do more. Even though the promise of this new stuff is that you don’t have to do as much ’cause the machine does it, instead, the reality, at least right now, is, perhaps while people are figuring it out, it’s like you have to do your old job, which already maxed you out.

You were probably already at

Jesse: least…

Exactly. Everybody was already plenty busy.

Peter: Yeah. Yeah, you were already maxed out, and now we’ve just layered on this new thing you have to figure out, and we’re pretty much giving you very little guidance about that.

So that’s my primary takeaway from Config. I honestly could care less about Figma and its product suite and whatever that indicates. I don’t think that’s nearly as much of a bellwether or harbinger as maybe it used to be.

But yeah. The sentiment curve has shifted from fright to just tired.

Jesse: Mm-hmm. Mm-hmm. Yeah, I think it’s interesting to note, first of all, the emotional tenor, I think the optimism is there, but it is I think somewhat muted relative to previous years. The people who are optimistic are a little more cautiously optimistic. It’s like the two sides are kind of meeting in the middle a little bit, that the skeptics are learning to appreciate a bit of what the technology can do and where it’s going, and the optimists have maybe had their irrational exuberance tempered a touch by the intervening year.

But I think that one of the things, and we touched on this in the Liminal conversations as well, one of the things that is a recurring theme for these leaders is the emotional resilience required to continue to manage ongoing change, and the fact that none of this is gonna be settled soon.

And in fact, the new steady state is an extreme unsteadiness for a lot of leaders in a lot of organizations. And in some cases, I feel like people, what they’re honestly looking for is something to anchor to that’s proving hard to find.

Peter: And I think it will continue to be hard to find for a while. Earlier today there was a post on LinkedIn that I ended up reposting with a bit of commentary. I forget the name of the woman who wrote it, but she was talking about her job hunt journey.

She’d been… I don’t know if she’d just quit or been laid off in January. It is now June or July, she’s starting a new job. And she had statistics to go with her job hunt experience. Within those statistics was, she got through all rounds with 10 different companies, right? Which is a strong signal at least when I run recruiting and hiring. If you make it through that round, you’ve got a one in three or one in four chance usually, right? There’s not many candidates get that far.

So 10 companies, she made it through all rounds. But then after getting to that point, she pointed out with four of those companies, something went haywire. The hiring manager quit or got fired, there was a reorg, there was layoffs, there’s something organizational occurring in 4 out of the 10 companies.

So these are companies that thought they were stable enough to go through a recruiting and hiring process, get through, I’m sure, multiple candidates through many rounds, and oh, and then at that point it turned out they weren’t that stable.

Some organizational chaos occurred and the job just disappeared, right? The requisition disappeared.

And what that to me was a sign of, or is a sign of, it’s anecdata, but, I’m seeing other indicators, and it goes with the exhaustion thing, is that companies have lost their collective minds right now. The degree of instability within corporations, I mean, it’s been high for a while, and it seems higher now.

When you talk about listening and signals, like one of the signals I’m getting is just a greater degree of uncertainty. It’s not necessarily layoffs, although that’s part of it. You and I have had friends recently who just found themselves without a job in the last few weeks that…

Jesse: mm-hmm.

Peter: At large, massive, otherwise seemingly very stable companies.

Jesse: Stable-looking. Yeah.

Peter: Yeah. And it’s just like, the analogy that just came to mind is, we’re all on a ship.

That ship is just rocking, and we’re all just holding on to the ship for dear life as waves are coming overboard, and we’re just trying to make our way through this period until the seas calm down.

Jesse: Trying not to get too sick over the rails.

Peter: Well, yeah.

Jesse: Yeah. Well, I think that, and you touched on some of these teams that have been really decimated in the last year, design teams out there that have been for whatever reason, one reason or another, they ran out of runway before they could get aloft and what these teams are facing now is, in some of these cases, you have these teams that have been so severely cut back that they have to renegotiate their mandates because they can’t keep doing what they were being asked to do before under these new structures. And the leaders are in the position of having to do that renegotiation of the value prop of their team, right? Of what we’re here to do and what we’re here to be measured for and what you can look to us to provide.

The organizational and cultural shifts are as, at least as radical as the technological and process shifts.

Peter: Well, y- yes, and I don’t think it’s necessarily just a matter of cutting back, though that’s definitely happening. So I conducted a listening tour, or I’ve been conducting a listening tour of design executives. It was something I was doing in May before I went out on a family vacation.

And I talked to about 20 design executives. I’m still poring over the data. But something that was intriguing to me is of those 20 design executives, three or four were between jobs. Like I hadn’t realized when I’d reach out to them they weren’t working.

But they hadn’t been laid off because of reduction. Each of them wasn’t working because there had been a leadership change in their organization, and the new leader didn’t want them in the org. Which, kind of, again, is speaking to a certain organizational chaos. The senior leadership are encouraging change within design organizations that involves just getting rid of current leaders.

Not the whole team, just like, “That person doesn’t belong here anymore.” And sometimes it’s a new leader wanting to put their people in place. I just had something outside of the listening tour, but a friend just got fired really, not even laid off, because a new CTO is like, ” We’re gonna do things different now.”

And I think as part of this chaos, something I believe is at the highest levels of a lot of these organizations, there is leadership turnover right, in the C-suite or just below.

Jesse: Mm-hmm.

Peter: That seems to be happening more often in the last year or two, and what we’re seeing is the impacts of that, the ripple effects of that within design.

It might take three, six, nine, 12 months to finally get to design, depending on the size of the company. One firm that you and I are familiar with, had 50,000 employees, so it took a good nine months between the new CEO…

Jesse: yep.

Peter: …And the leadership shift. But in most of the cases I’m aware of, it’s not about reduction, it’s just about turnover, and, on the part of these senior-most leaders, a total disregard for the turmoil they are causing.

Jesse: Hmm. Mm-hmm.

Peter: Just disregard, disinterest. You’d think you’d want some degree of stability so that the business can do its work well, and there’s absolutely no interest in that from what I’m witnessing.

Jesse: Yeah. Well, it’s interesting to think about just the sheer number of people who have some qualifications for leadership or management roles in a digital product development or design organization who have been turned out on the market in the last couple of years, which has really made it a buyer’s market, so to speak, when it comes to especially middle management.

So, I’m seeing the same pattern that you’re describing of these wholesale leadership turnovers. You get a new CTO brings in a new CPO brings in a new VP of design, and the ripple effect goes all the way down. And just by virtue of having been in the organization a while, you become perceived as a liability to the new order, so to speak.

And so for leaders, it then becomes this politics game of proving in that nine months, that you deserve to stick around.

Peter: You used the word order.

Jesse: I know, and you’ve been talking about chaos.

Peter: Well, and I think concomitant with this upheaval is, at least for me, an increased recognition that the people running these companies, that m- many, I don’t know about most, executives are just bad at their jobs.

They’re not accountable, right?

They’ve had– they wouldn’t be in that role if they hadn’t had some success. I tend to, in private conversations with folks, just disregard this class of executives as dumb or stupid and that’s probably overstating it ’cause, again, they probably would not get into that role if they were categorically dumb. If they were just dumb. They clearly knew something, figured something out, got into a position of authority and influence.

I suspect their wisdom is very narrow, though, and now they’re in this broad– they have the much broader mandate, and they’re trying to apply this wisdom from their narrow point of view to the broader mandate, and that’s where the stupidity is.

And as I continue to reflect on that, design was probably never in whatever that narrow band was.

Jesse: No, it never was. Yeah.

Peter: And so the moment it expands to include anything that might include design, design will not be treated well because those executives, like we saw with Cloudflare where once the design system was put in an LLM, the CEO’s like, “We don’t need designers anymore.”

Because he’s an engineer, and he just sees the world as, like, a machine you fiddle with or salespeople to sell it, and has no understanding of kind of the actual value that design was delivering, ’cause the only sense of value he perceived was the creation of assets or screens for engineers.

Jesse: Yeah. Yeah. So again, it comes back to the value the design is delivering, the way that value is perceived, and whether it’s your AI transformation strategy or how you manage the politics of this kind of organizational change, it’s on the design leader to keep their eye on what that value prop is.

Peter: Well, and to figure out how to communicate it in a way that resonates with, hopefully, people who are listening. Something I wonder, you said earlier that this is this new kind of unsteady state.

Jesse: Yeah

Peter: I was about to call it a steady state, just meaning we’re gonna be in this state for a while, but that state is…

one steady state of unsteadiness, yeah

of unsteadiness, yeah.

This is something I’ve found myself thinking about potentially developing some training material around which is, what can design leaders do to

maintain resilience and even ideally not just maintain, but thrive in this discombobulated mode. I’m wondering where your thoughts go.

Jesse: Yeah, no, I think you’re right to call that out. I had a client a while ago who went through another performance review and said to me, “Look, I’m tired of being called out for my resilience. I’m tired of my brand being my ability to take a bunch of hard shit and stay standing. I’d like for this career to mean something more than that to me.”

And I think that’s right on. And in, again, going back to the liminal conversations, those explorations, I think were about trying to figure out, well, what is the skill set that allows you to remain upright and not be knocked about as much? But I do think also that thriving means taking control of the narrative. I think thriving means taking control of your destiny.

In a lot of organizations, the constraints are so severe that becomes practically impossible for leaders. And, it almost goes back to the leadership ceiling kind of stuff, like where can you actually move your constraints or influence your constraints to create new opportunities for yourself and for your team?

Jesse: A lot of this stuff also resonates with the survey that was released a couple of days ago through Lenny Rachitsky’s newsletter. And I’ve forgotten the name of the researcher who conducted the study, but

Peter: Noam Segal.

Jesse: All right. So Noam, thank you for your work. It’s very interesting stuff.

What came out of this, especially as it connects with some of the things that have already come up in this conversation, one of their findings is that the current norm is chaos, that across the board people are reporting just organizational disarray broadly.

And they don’t do a lot to try to identify root causes for that, but it definitely is one of the big patterns that came out in their study.

So they talked to I think close to 6,000 self-reporting, subscribers to Lenny’s newsletter who volunteered to take the survey. The other thing, aside from the chaos, actually this was a finding from Andrew Hogan’s work for Figma as well in their AI study, which was that there is no one central kind of experience that people are having right now.

Everybody’s experiences are all over the map. It’s like I was saying about AI transformation a couple of episodes back. Every path through this wilderness is different because every organization is starting from a different starting point with different resources and different cultural advantages and liabilities that determine how steep the climb is through all of this stuff for people.

Peter: Yeah. In a pre-AI world, things had settled into a few different archetypes of organizations, at least with respect to their relationship to design. Think about your maturity model or something, right? And it’s got three or four stages and where you fit in that.

I’m doing a bit of just follow-on research. I launched a pulse check survey specifically for designers to get a sense of how they’re feeling.

And after 100-some results what’s interesting is a similar story, which is there’s no narrative. There’s no theme. It’s scattered. My listening tour revealed that as well with the 20 executives that I spoke with. And I guess that’s part of being in this moment.

One has to imagine shit’s gonna settle down. But It’s interesting to me that as things become less existential, I would think we’re starting to approach this with a more pragmatic point of view, right? As opposed to a hair on fire point of view. You would expect the settling to start, but it’s not.

So I’ve got Lenny’s thing up here, and there’s a chart showing that from 2025 to 2026, burnout increased by 20%.

Jesse: Mm-hmm.

Peter: And optimism decreased by about 10%. And so even though we’re kinda getting our hands around this, we’re not feeling any better about it.

It’s not getting us into a calmer mode. It’s also weird, though, he had this question about how much better are you at your job? And about half of the respondents said very much or extremely better. Now, I would love to see that cross-tabbed with different functions.

I’d be curious what percentage of designers would say that. I mean, engineers, yes, I’m sure they consider themselves largely better at their job. But I still suspect a lot of designers would say that they are feeling very much to extremely better at doing their own work, if they can just put a little boundary around that.

But also recognize that, yes, I can do my thing better, but the space in which I’m operating,

Jesse: But the rest of you

Peter: is not.

Jesse: Can’t be trusted. Yeah. It’s interesting to think that people can more readily feel optimistic about the individual scale impact, but when that starts to add up to an organizational scale impact, then they get nervous about it.

One of the things in Noam’s survey was the notion of What are you afraid is gonna happen with AI? And people are not afraid of losing their jobs. They’re afraid of having more work piled on their plates. To your point, they were already busy before this stuff came along, and more than half of the people in the survey said that their worry, the top of their list, was: expected to do more work for the same pay.

So the sense is that the executives and management are just going to continue to increase this pressure on teams to be productive and to perform. Again, which is why for managers and for leaders I think you’ve gotta get really clear on the value that your team is delivering and making sure that you’re optimizing for that.

Peter: Well, and this is an expression of executives taking advantage of what they see as an employer’s market, right? When it was an employee’s market, you get a bunch of glorious perks. You get massage and free lunches and all this other stuff. Plenty of vacation time and all that.

But when it’s a employer’s market, at least in the United States where we are without any meaningful employee protections, yeah, they’re just gonna keep piling stuff on you, and if you can’t do it, they’ll fire you and see if they can find someone else who will do it.

Jesse: Yeah.

Peter: And they’ll find someone who will raise their hand to do it ’cause there’s a bunch of people out there who need work.

Jesse: Mm-hmm.

Peter: I don’t quite know what the solve is for that besides unionizing or uh, some other form of collective bargaining. But that’s not actually u- unions won’t aid many, most of the people who listen to this podcast ’cause they wouldn’t be in a union because they’re management.

Jesse: So what is, do you think, the impact for people who are in management or leadership roles here? So if, and this is another finding from Noam’s study, the burnout is becoming sort of the dominant place where people find themselves in this industry, as leaders, we have to take responsibility for that. We have to take ownership of that in some way, even if we ourselves are also feeling it.

Peter: Related to that, and if we wanna talk more specifically to our podcast audience, in answer of the question: How likely are you to recommend a career in your role to a friend starting out today? Far and away the lowest scores were design and research. Everything was actually below zero, so no one– on average, no one would be recommending a role in tech to a friend, which holy shit.

But design and research is far and away the lowest.

Which also actually pairs with another finding in here, about the value of management and managers and how manager effectiveness was correlated to burnout and job enjoyment. And so people who felt their managers were extremely effective rated four out of five on job enjoyment and well below the average on burnout.

But and then there’s a note, there’s not specifics, the worst rated managers cluster in data/analytics and design.

Yep. And so, there is a need for our peers, many of the people listening to this podcast. Though probably if you listen to this podcast, you’re a little ahead of the curve.

Jesse: We hope so.

Peter: We hope so. But, we’re not doing our job. Why are design managers the worst rated, right? What is it that they’re doing or not doing, causing their teams to feel ineffective and burned out and hate their jobs, right?

I could speculate but regardless of the speculation, it’s easy for designers to point fingers at others in situations like this, but I actually go back to part of the reason I wanted to write Org Design for Design Orgs a decade ago was because I saw designers pointing their fingers at all these other people about why their team was not as effective as it could be.

Product isn’t doing this, and engineering isn’t doing that, and leaders don’t understand us. All of which might be true, but if I looked at almost any design org in 2015, they were poorly run.

The person in charge didn’t know what they were doing. They didn’t know how to set up a team, an organization, a structure.

Jesse: Yeah

Peter: Yeah, so I wrote the fucking book to, like, here’s a playbook to, like get out of your own way so that at least you could then credibly start complaining when others aren’t doing their job, or when their behavior is affecting your team’s ability to perform.

I suspect though that, a decade or so later, that most design orgs are still just poorly run entities because the people in charge don’t know how to do it.

Jesse: Yes and, maybe this is too charitable a stance, I don’t know. A lot of design leadership roles are not set up for success. They’re reporting to the wrong people. They are supported in the wrong ways. They are granted the wrong scope of authority to actually deliver on what they are on the hook for. So I think it is important to separate incompetent managers from poorly constructed management as a system in an organization.

Peter: I have research that would support some of what you’re saying. But, part of me would want to be able to control for those factors with other functions, right? Does, engineering perform better or whatever because it’s in the right place in the organization or given the right mandate? Marketing, sales?

Marketing and sales is actually funny in this report because there’s a section in the report around, different functions in their relationship to whether they are destabilized or diminished, tired, overwhelmed, anxious, worried about losing their job, or would recommend to others. And what I thought was super interesting about that was that sales and marketing folks, would do things like, they would score badly on things like being tired.

They’re more tired than most other functions. Salespeople are more overwhelmed than most other functions. But sales and marketing folks were also the least anxious and the least worried about losing their jobs. Oh, and the least destabilized in their role, they felt like they’re just continuing to do their work.

And so I thought it was super interesting and so it was design, research, engineering, operations, PM, data, sales, marketing, and whether or not you were a founder. Sales and marketing are the two functions that are not specific to tech…

Jesse: mm-hmm.

Peter: That have been in businesses for 180 years or whatever.

Jesse: There are a million, billion businesses out there that do nothing with tech that have still got those functions. Sure.

Peter: Not only that, but 130 years ago when General Motors or whatever, railroad or Procter & Gamble or whatever company is, starting, like they know they need sales and marketing. So there’s a longevity there as well that seems to be allowing these folks to be less anxious and worried regardless of if they feel like they’re tired or overwhelmed.

And so part of it is likely due to the newness, right? Of all the functions, this is something I beat on. Of all the functions, particularly that have gotten some degree of first-level recognition within an organization in design and research it’s spotty, but it’s there. Design is the newest.

Design and Research

Jesse: Yes.

Peter: are the newest.

And so I think part of it is we’re still figuring out where we belong. We’re still figuring out what our mandate is. We’re still figuring out our value proposition, both ourselves and communicating it to others.

Which then leads to another contention that I continue to have, which is that design leadership is the hardest of the leaderships because of this. I occasionally get pushback on that, but there’s mounting evidence to support my contention.

But the design leaders are also just perfectly willing to shoot themselves in the foot and wallow in their ineffectiveness by not shutting up about craft, right? Like, lauded, elevated, vaunted members of our practice, their primary message is the importance of craft when literally no one else in their organization cares about that stuff.

And it’s fine. Craft matters. We all know that it matters. But if you as a design manager are spending most of your effort on ensuring craft within your organization and not effectiveness, right? The word that they used in this research was effectiveness. ” Not effectiveness” as a manager. And effectiveness I would expect it to mean, if you’re asking if a manager’s effective are they able to have an impact and get things done and move things forward or whatever, right?

Jesse: Mm-hmm.

Peter: Craft is interesting only to the degree to which it drives impact. But designers are really bad at caring about impact and caring about being effective, right?

And that’s where I … It doesn’t matter where they are in their organization, who they’re reporting to, or whether or not they’re set up to succeed. There’s still this mentality that many design leaders and design managers have that their job is not one of effectiveness and impact. And then they get dinged in surveys like this.

Jesse: So if I think about where the leverage point is on this topic it seems to me that it has to do with the tone that is set by design leaders, the culture that they create, and honestly what they hire for.

In that if you as a design leader have put in place a bunch of senior practitioners who are all craft-forward ICs, and that’s all you ever hear those guys talk about, you’re creating an environment in which these are the ideas that we care about, these are the ideas that get reinforced, these are the conversations that we have about design on an ongoing basis.

And it seems to me that to break out of the craft trap, the manager has to consciously, deliberately, intentionally drive a different kind of dialogue within the design team itself about what they’re doing and why.

Peter: I think that’s right. Some of this goes back to my mediate the membrane concept, right? Where the work of design is just so different from the work of the rest of the firm that designers are part of, and the role of design leaders is to serve as this interface between the two. And part of that is communicating to the design team the importance of understanding the business context in which they’re operating, ’cause that is how you become effective.

And vice versa, communicating to the rest of the company the distinct practices and value that design can deliver. We talk about not just clarifying a value proposition, but expanding that value proposition.

Jesse: Yes.

Peter: There’s work that the design team could and should be doing that’s likely not happening, that the design leaders need to articulate in some way that it will resonate with those folks outside of that design org.

And, that takes work to figure out how to land those messages. I had an interesting conversation this morning related to this. So I’ve been teaching a masterclass through IF Design Academy, the class wrapped up, so we were having a wrap-up conversation, and then we were talking about the most popular other class in the academy, which is on hold, hold… business and design.

The class that people are most interested in taking is basically an MBA 101 class. And it is far and away the most popular class because all these design leaders are like, “I need to understand business.”

The first thing that Garan does in his class is say, ” We are never going to talk about the business value of design. We are not gonna talk about clarifying the value of design. No one in the business cares. I am going to teach you about business. I’m going to assume that you’re like a, an MBA student, and you’re here to learn how business works, and that is what I’m going to teach you. Afterwards, you can figure out how to take what I have taught you and make it relevant to your world, but we are not here for you to justify or validate or whatever the business value of design because no one cares.”

And as this was being explained to me, I was reflecting on it. I’m like, ” Yeah, like, everyone else in the business understands that calculus…

Jesse: right

Peter: …except for designers.”

Jesse: Yeah

Peter: They all are just running spreadsheets and making, doing math or whatever the thing is to communicate in the language of the business. And designers just can’t get over themselves enough to just do that, to shut up about design for a while and just take part in that conversation.

Jesse: It’s so interesting how this stuff just keeps coming back to fundamentals. The fundamentals of politics and managing those relationships with your executive stakeholders as well as your cross-functional partners. The fundamentals of business and design and spreadsheets and all of that stuff.

Peter: As this was being shared with me, I was reflecting how 25 years ago, almost to the day or something, right, Adaptive Path published a report on ROI and design, right? And we talked about ARR, and we talked about NPV, and we talked about all this shit. And I’m just like,

Jesse: What’s

Peter: why isn’t it sticking, and why do design leaders continue to say that this is the most important thing for them to learn, say that this is the lacuna in their practice?

I heard that on my listening tour as well when I asked folks how they could be a better leader. Almost half of them said basic business acumen.

Jesse: Yeah

Peter: One, it’s not that hard. The heart of business is the simplest, dumbest math.

And it’s not like it’s been a secret for the last 25 years, much less, just, you’re in a business, of course, you should understand how business works.

It’s mystifying how there’s something about this subject that is just…

The image I have in my mind is designers look at this subject, and it’s as if they’re looking through a clear glass window, but then the glass turns opaque, and they’re just like, “Doop.” Just poof. Nope.

Jesse: Yeah, I gotta wonder about, I mean, first of all, I think it’s important to look at Noam’s study with, a bit of a grain of salt in that again, these are people who self-responded, people who were subscribers to Lenny’s newsletter. Design and research together only make up a little over 10% of total respondents to the survey.

Product management nearly closing in on 50%, 46.9. So nearly half the people who responded to this survey are coming from an entirely different perspective. In fact, almost everybody who responded to this survey is coming from a different perspective than the perspective of design and research.

And I would say the other thing is that it skews really senior because of his newsletter and its audience. So he’s got uh, right around 11% are people in design and research functions, and right around 11% are also people who are founders or, senior level executives. So, the founder class is as represented as the designer class in this data and it skews accordingly.

I thought this finding was hilarious that founders are the happiest ones in technology, ’cause I’m like, ” No shit, man. When has that not been the case?”

Peter: Well, yeah and the implication I would argue is that things would skew even more negative if these populations were normalized. And when they do slice it by these populations, you see that negativity shine through. ‘Cause I still think even though it’s only 10%, if you combine design and research, 10% of nearly 6,000 is still 600, right?

So that’s a decent population. I’m– I feel good about the signal he’s getting about design and research more than I would say about data and analytics at 3%,

Jesse: Yeah. Well, all I’m saying is that when he’s not talking about design research specifically, that data we ought to be looking at through more of a product lens, because those are the people who are responding. Yeah.

Peter: So something else I wanted to bring up, which kind of touches back on our podcast miniseries, Liminal, and our friends Jorge Arango and Greg Petroff, who have a business called Unfinishe. Because So I’m helping prepare or program the Design Leadership Summit in November, taking place in Toronto.

And as Preet, who is the primary organizer for the event, and I have been talking about the programming, we were batting around thoughts on theme.

And the theme that we are landing on is this one of unfinished. For me, it all started with our conversation with Roger Martin, and trying to figure out what happened after 2009 when there seemed to be this opportunity for design to be more expansive, to have that broader value proposition.

And then over time, that just narrowed and narrowed until starting around 2015, 2016, and we adopted product designer as our primary mode, and that was seen as someone who produces screens. And the AI moment has really highlighted that limitation, but also an opportunity, to recast our value proposition.

And as I’ve been thinking about that, I’m like, I feel a little bit like Jack from Lost. “We gotta go back.”

Jesse: Spoilers

Peter: Sure, for a 20-year-old television show.

And, go back to that period of fecundity and hope and potential that we were scratching at in 2006, ‘7, ‘8, and ‘9. And embrace that broader mandate.

And I’m hearing and I’m seeing some signals to that. Something I didn’t mention coming out of Config not a big thread, but a persistent thread, and I hadn’t only heard it at Config, is the rise of service design. Is this something that you’re hearing?

Jesse: A bit, yeah. Yeah. I mean, there’s definitely, I think, an increased interest and awareness of the value of it, if not necessarily… You know, the investment is always gonna lag that. But I definitely had more than one conversation with design leaders about service design at Config, and in the last several months it’s been coming up more.

Peter: Yeah, I’ve been surprised by that, and I think there’s just something about the overwhelming complexity that,

Jesse: I think

Peter: everyone is facing.

Jesse: Everybody needs more context in order to make better decisions, and if that context is something that can be incorporated into some of these AI-driven workflows, then that’s an advantage.

You know, my hope is that there’s mountains of good, valid service design work out there that’s currently languishing in PDFs on various shared drives that can be potentially unleashed here.

Peter: Going back to this theme of unfinished. So not just that we need to go back to 2008 and pick up that thread, though that’s part of it.

But this recognition that to a certain degree, design is always unfinished. I’ll read here some language that I came up with.

Design’s work is never done. You wanna treat design not as a fixed function, but ongoing infrastructure. The work of design is, if we get to Herbert Simon-land is to improve conditions. To be a designer is to always improve, and if you’re always improving, you’re never done, right? You’re never finished.

If I don’t wanna be down on things, when I’m trying to pick myself up and look at the potential, there’s potential. There’s some signals, like we just talked about with service design.

There’s some signals like we’re seeing some teams are shifting left as the production function is being…

Jesse: yes

Peter: …consumed by AI.

And I think as there’s an opportunity to reintroduce that broader mandate for design, hopefully, we can take advantage of the things we’ve also learned in the subsequent 20 years about doing a better job communicating, connecting with the people around us.

One of the reasons we struggled back then, or the mandate didn’t stick is, that expansiveness had very little to do with our express effort to make it so, and instead was more a reflection of forces outside of our control. Apple’s success and some other kind of realizations that like, oh, people want good experiences and are willing to pay for it. But not really driven by design.

And now 20 years later, how do we make that better case for ourselves to connect with these things and not wait for,

Jesse: Yeah

Peter: moments outside of our control to give us permission, but instead how do we make our own permission, kind of like making our own luck to do this broader work?

Jesse: Yeah. And I think that’s an example of what I might call out as the general pattern or the general recommendation that I would make here, which is to use your leverage to be the antidote to these negative trends.

If the trend is burnout, create a culture that better supports people. if the trend is disempowerment and commoditization of your team and its value, then fight for and work toward a less commodifiable…

Thinking again about the comparison with sales and marketing. They have skill sets and knowledge and expertise that is not easily replicated by automated processes. That’s why they feel secure. Find that same security for yourself and your team. I think the opportunity for leaders is to take the microphone, is to set a new tone, is to assert what’s true because in this place of chaos right now, going back to liminal, the chaos contains within it the seed of possibility.

It contains within it the opportunity to create a different kind of order out of this chaotic moment.

Peter: And it will require design leaders to lean on the leadership part of that phrase and not the design part of that phrase.

Jesse: Yes, exactly so Peter, thank you so much for the conversation

Peter: This has been great. I’m actually excited by where we landed

Jesse: Cool. All right. Thanks

Peter: Until next time.

Jesse: For more Finding Our Way, visit findingourway.design for past episodes and transcripts, or follow the show on LinkedIn. Visit petermerholz.com to find Peter’s newsletter, The Merholz Agenda, as well as Design Org Dimensions featuring his latest thinking and the actual tools he uses with clients.

If you’re looking for help with AI transformation or you just need a private advisor to help you solve your hardest leadership problems, visit my website at jessejamesgarrett.com to book your free one hour consultation.

If you’ve found value in something you’ve heard today, we hope you’ll pass this episode along to someone else who can use it. Thanks for everything you do for others, and thanks so much for listening.

Dave Gray, author of Liminal Thinking and founder of School of the Possible, joins Peter and Jesse to examine what’s actually getting in leaders’ way right now: not the disruption itself, but the expertise that blinds them to it. The conversation moves from beginner’s mind to the compression of corporate work, landing on a provocative question — what does your value look like when you define it yourself?

Dave Gray’s School of the Possible: https://schoolofthepossible.com/
Dave Gray on The Practice Economy: https://schoolofthepossible.substack.com/p/the-practice-economy
More on Peter Merholz, his consulting, coaching, and training offerings: https://petermerholz.com/
More on Jesse James Garrett, his AI Transformation Consulting and Leadership Coaching practices: https://jessejamesgarrett.com/

Jesse: I’m Jesse James Garrett,

Peter: and I’m Peter Merholz.

Jesse: And we’re finding our way,

Peter: navigating the opportunities

Jesse: and challenges

Peter: of design and design leadership.

Jesse: This is Liminal. On today’s show, Peter and I welcome Dave Gray, veteran design consultant and author of the book Liminal Thinking. We’ll get his perspective on the mindset and skill set that can help leaders navigate this liminal moment. We’ll also examine the blind spots that result from too much expertise, the future of corporate politics in agentic companies, and defining your own value outside the terms of the corporation.

Peter: Dave, welcome to the show. Thank you for joining us.

Dave: Thank you for having me. I’m thrilled to hang out with you both. It’s been a long time, and we’ve had many experiences together. I’m happy to see you again.

Peter: We have. I remember events going back almost 20 years now where we’ve talked together. But the reason we asked you to join our show is, we’ve been doing this series of sessions on this concept of liminal, liminality, the liminal moment we’re in. We remembered early on in that, that you wrote a book… called Liminal Thinking: Create the Change You Want by Changing the Way You Think.

And so we know that you’ve been thinking hard about liminality and the role that it plays. And so, yeah, we wanted to get your thoughts on this matter. But maybe even before we dive into that, what have you been up to? I know what I last recall is you were a consultant at Xplane, and then you’ve been on your own, and you host communities. What do you do?

Dave: Yeah, so before we leave the topic of the book, I don’t know if I ever told either of you the story of the book.

I didn’t start out with some idea that I wanted to write about liminality. It started out as something totally different, and it evolved into that. So maybe we can get into that.

But yeah for 30 years I was a design consultant, an innovation consultant. I did a lot of drawings and mappings for large organizations, helping them think through change programs and complex technologies and making them accessible, to sell them usually.

And I exited that business, and I was faced with the question, what are you gonna do now? I sold my company and I just started thinking “Well, what is Dave as a service? What would that look like? What is it that people come to me for when I’m not selling anything? What is it that I like to do? What is it that people come asking me for?”

Dave: And yeah, so that’s what I’m doing right now. You could call it Dave as a Service. My name for it is The School of the Possible. It’s a company of one. Me doing the stuff that I enjoy doing in service to a community of creative people.

It’s kinda like a Zoom version of a bar.

Peter: Okay.

Dave: I’m like the, you know, the bartender…

Jesse: everybody knows your name.

Dave: Yeah, everybody knows each other’s name. Make sure that everybody has a comfortable seat and it’s like a bar meets an art studio.

Jesse: You know, one of the reasons that we wanted to talk with you is because liminality has been such a focus of our conversations lately, and you literally wrote a whole book about it. It’s not a new book. I was astonished to discover that this book is almost 10 years old now.

But it is a book that has had some resonance over this last decade. It is a book that I continue to see people reference and call back to. And for people who aren’t familiar with the book, I wonder if you can encapsulate a little bit about the origins and the ideas that came out of that, and what were the big themes that you were trying to drive with writing a book on liminal thinking?

Dave: Yeah. The story of the book, it’s not one that I tell very often, but I think it’s a really interesting one, because it started out with mutual friend of ours, Lou Rosenfeld, he’s, very good about remaining connected with his authors and prospective authors.

And I just had been his friend. And he sent out a little note to his email list asking if anybody knew anybody who wanted to write a book about Agile, Agile software development. And I was like, ” I think that’s really interesting.”

I had just finished a book called The Connected Company. A lot of it had to do with Agile kinds of approaches and techniques to organizing business. And I said, “I don’t really know much about it, but I would love to write a book in the kind of journalistic style. I’d love to go out and interview people and learn about it and write a book that way.”

And he said, “Great.” So I started out to write a book about Agile and

Peter: This is, like, 15 years ago or something now?

Dave: Something like that. And so I started interviewing these people. Agile software development, coaches, professionals, experts, and I’d ask them about agile, and they would say “We know what agile is, but we can’t do it.”

And I’m like, “Okay well tell me about that.” And I kept hearing from these people, who all seem to look like me. They’re, like, very homogenous from a diversity perspective. And I kept hearing the companies are structured in such a way that “We can’t do it. We can’t be agile.”

And I thought, “Okay, that’s not agility then,” to me, because agility, to me, is you’re able to do things in spite of the environment, or you’re able to navigate within an environment that you don’t control in such a way that you can maintain some kind of balance or equilibrium.

So I went back to Lou and said, ” I think we gotta think about this book differently.” And I expanded the group of people that I was talking to.

It got much more diverse, much more interesting. Talking to people, soldiers, people who are in environments that they can’t control, literally, someone’s opposing their efforts. Humanitarian aid workers, firefighters.

And I started learning about real, I guess, what I would call real agility. People who are able to operate these very complex, super volatile, rapidly changing environments. They’re able to achieve some kind of results without having control.

And I think that’s very connected to what you guys have been talking about, this idea of, feeling like there’s rapid change going on. You don’t control it. You’re not in control of the situation, and yet you have you have things that you wanna try and achieve.

And that’s where the book ended up going. And what was really interesting to me is a lot of it ended up being about mindset, and a lot of it ended up being about a lot of the stuff that gets in your way in operating in these kind of volatile complex environments is your own way of thinking about them.

A lot of the barriers are inside your own brain, so to speak.

Peter: Before we got on mic, we were talking a little bit about the tenor of the discussion right now in places like LinkedIn. Where there’s a lot of people having a lot of feelings. They might be anxious feelings, they might be positive feelings, excited feelings. We’re in a heightened moment. Feeling like they’re out of control.

And it’s interesting to me that those initial folks that you spoke with for the Agile book felt like they lacked control, because agile was seen as a net good, right? Companies were becoming agile, and, like we’re hearing about AI, there was, like, almost this mandate: We’re going to adopt Agile.

And then people like, I’m assuming the ones that you were interviewing, are brought in to help us become agile. So these folks should have tailwinds, right? They’re the ones who are being seen as the ones who are gonna lead us to the promised land.

But even those folks were feeling stymied, right? They got frustrated. They kind of threw their hands up. Which is a little different than what’s happening right now in a lot of organizations where we’re getting this top-down executive mandate about AI, but no one knows how to do it.

Like, at least there was a group of people who could claim some expertise or some understanding of how to drive agility with some evidence in it. Right now, with rare exceptions, it just feels like we’re all making it up as we go.

In the Agile moment there were these organizational or corporate constructions or strictures that prevented agility from arising.

I’m curious, as I’m sharing, a little compare and contrast, what you make of these different moments. When agile was imposed on us, and we had the right people to help get us there, and we couldn’t figure it out, what hope do we have in this moment?

Dave: Oh, wow. We’re all probably roughly somewhat near the same age, and we’ve probably all lived through a lot of different disruptions over the course of our lifetimes.

I remember before the internet, at least before it was a thing that people used all the time.

And I feel like I have a little bit of an advantage because I have been through so many of these that I’ve start to see a lot of common themes.

And when you think about AI, the one that feels the closest to me as a designer was more like in the ’80s, when PowerPoint and graphical user interface, and suddenly everybody was able to make presentations and, PageMaker and, suddenly, you know, a lot of people who were in the design field were really freaked out because now my boss can make the whole magazine, like whatever.

That was at least what we were afraid of at the time, and it’s like, there’re still designers, but there have been so many times when there’s been a prevailing idea that design is going away or that technology’s gonna take over that job.

I forget who the painter was who’s, when photography came around, said, “This is great ’cause now we know what painting is not.”

And I think it’s like, as we look at AI, one way to look at it is to see all the things that it’s gonna take away from us.

But another way to look at it is to say, think of that as an editing out of the stuff that maybe we didn’t need to be doing anyway.

Jesse: So you talk about identity. You also talk about skills, skills and tools, and the way in which we get attached to those things as a part of who we are. And we’ve talked on the show in the past about this same moment that you’re talking about here, where digitization starts to supplant really well-established practices that have been in place for a really long time.

The example that comes to mind for me is in the field of accounting. Let’s go outside of design altogether. Accounting practices stayed more or less the same for hundreds of years until computerization started to change what your role was, and suddenly your penmanship didn’t matter as much.

Whereas previously, like, this was part of how you got the job in an accounting office, was you could write clear numbers that other people could read, and these kinds of granular skills that then become much more fungible as the tooling evolves.

But I wanna come back to the notion of the liminal mindset and what came up for you in your explorations of how people address these moments of change and what it takes for them to not get left behind, to not get left in that place where they’ve got the paste pot and the X-Acto knife instead of the mouse and the keyboard to be able to do their jobs back in the ’80s and ’90s.

Dave: I have a quote that I love. It’s from Mark Twain. It’s an old one, but he said, “it’s not what you don’t know that gets you into trouble. It’s what you know for sure that just ain’t so.” And for me, that’s such a great quote and so relevant today.

Another way of saying the same thing is, Shunryu Suzuki who said, “In the beginner’s mind, there are many possibilities. In the expert’s mind, there are only a few.”

And I think this is the thing. Over many years, you build up expertise, and the expertise enables you to be very effective and efficient, like ability to use certain tools, your penmanship, to your example, other things. Those skills, you start to think of them as part of your identity, of who you are.

But all that focus, it’s kinda like horse blinders. It eliminates your peripheral vision, and it actually gets in the way of you seeing what’s actually going on if things are changing in a very fundamental way.

And I think that’s what’s happening now. Things are changing in a massively fundamental way. To a beginner, someone new to the workforce coming in, they’re not gonna have all the knowledge that gets in the way of them seeing what’s actually going on. They’re gonna be like, “Oh, I can just get on AI and I can do this, and look at that, I made an app. Whoa.”

And I think this is a common theme of a lot of these tools that come along. They create a new level of abstraction that wasn’t available before to the work. For example, when I started, before the Macintosh, before PageMaker and all this stuff, it was really important that you had to be able to use a ruling pen. Okay, a ruling pen is, you dip it in ink and it would make a very straight black line. With Adobe Illustrator or even MacDraw, that’s not a skill that I need to have with my hands anymore. And the people who are attached to the old craft are like “Yeah, but you don’t know how to draw a straight line. You’re letting the computer do that for you.”

Dave: A good analogy for me is you go from walking, to getting on a skateboard, to riding a bike, to driving a car, to getting on an airplane. At each stage you’re losing some level of contact with the ground and the detail and the granularity. You’re not gonna see the landscape in as rich and detailed a way from a car as you are from a bicycle or from walking. But, you’re increasing your capability.

So, what happens with the tool is they abstract you away from the ground. So now I don’t have to know how to write Python to code an app anymore. So there’s things that are happening that I don’t understand. Like, let’s say riding a bike. If you ride a bike a lot you have the ability to fix it yourself probably. You really understand how the whole machine works. You can look at it and understand it.

When you’re in a car it’s a little more complicated, but actually, a car is probably easier than riding a bike, as you gain more power and control at a more abstracted level, you’re losing power and control at the more detailed level. You’re losing your attachment and your groundedness to the work, but you’re also increasing the scope and scale of what you can accomplish.

And I think AI is just doing this at such a dramatic level. I’m not sure what corporations are gonna look like after AI’s finished, you know, burning its way through all the, all the- the shit, honestly, that we’ve been doing that is not gonna really matter that much when the AI can do it.

It’s like the version of the ruling pen in a corporate world, a lot of it is, oh, just the politics. Think of all the political back rubbing or whatever you wanna call it that goes on in a large organization and the jobs that are honestly, not that hard.

As a consultant going into large organizations, I felt, wow, there’s so much about just people’s egos and just making them feel important and so much political stuff about, oh, I don’t wanna piss anybody off and all this. When all that work is being done by agents, they’re not gonna need to, kiss each other’s asses.

Jesse: So, are you suggesting the rise of ass-kissing robots?

Dave: I’m actually saying I don’t think they’re gonna need it as much. A lot of that effort and energy and cognitive overhead that’s going into just managing the human aspect of bureaucracy is, I just think it’s gonna be dramatically changed, at the very least.

And I think, I have a picture of what work’s gonna look like on the other side of it. I think a rough sketch kind of picture of it. But I think it is gonna be much less of the fake relationship stuff and much more of the real relationship stuff that you don’t see a lot of in the large organizations.

Peter: Before we talked, you shared something you had recently written that I think you’re maybe starting to allude to, that you call the practice economy, and you talk about these waves of work and, agriculture being an early wave, and then you had industry and factory work being this subsequent wave as agriculture declines. And then industry declines as you have essentially corporate work becoming the latest wave.

We’ll link to the article in the show notes. There’s some charts and graphs that are a part of this. And you show the corporate wave actually peaking around 2000. And it’s actually been in decline for a while in terms of, this is the percentage of people doing this type of work.

And you can probably tie it to broad adoption of computers and the internet in the workplace, that initial decline of just what percentage of people are doing corporate work.

‘Cause you can imagine in a pre-internet life, you needed all these manual laborers who were, like, secretaries and assistants and all this kind of moving of information around. But once you had computers and networks, the mail room evaporates, and those types of roles go away.

Dave: Yeah, we used to have typists. That used to be a job,

Jesse: Couriers?

Peter: You think about “Mad Men.” Everybody had a secretary.

So that stuff’s already been going away, and I think what you’re suggesting is that it will go away maybe even more rapidly with some of this new tooling.

And what you have replacing it is the practice economy, and I thought that was interesting.

I’m gonna ask you to define it in a moment. But in our last episode, Jesse and I were talking about, maybe I had some mindset constraints because so much of my thinking as we’ve been talking about liminality is trying to help people survive in their current state, right?Wherever they are at, how can they navigate this uncertain moment and recognize that uncertainty as opportunity and come out the other side with some victory?

But I had, I think, implicitly been imagining people staying at their jobs and trying to make it work. And it was in our last conversation where I’m like, why am I assuming that? Why wouldn’t… if there’s a group of people in a company who recognize an opportunity, a new way of working, instead of trying to win over a bunch of executives or something as to do it, why not the four, five, six of them just leave and do the thing? Especially with the tooling we have now. You can get much closer to the work and just be gone.

I had to free myself of this assumption of working at a co-, context, and that’s the sense I have from what you’ve been writing with Practice Economy. So consider this a little tee up. I’m curious how it aligns with what you’re thinking or where your thinking is going here.

Dave: Oh, yeah. If you think about you think about the tech giants today, right? Mark Zuckerberg, college dropout, started Facebook. Apple, started by, in a garage, pretty much every single one. You know, EBay, a guy programmed it on a weekend.

Peter: Google in a garage by two guys who maybe didn’t finish their PhD. Yeah.

Dave: Yeah, right. And I have friends, and I’m sure you do too, that it is like even with a large organization with tons of money, so Xerox basically created Apple. They built the research center out of which Apple came.

They invested, they put the money in, they had all the creativity. They weren’t able to turn that into a company, turn it into an organization because, again, of that, I don’t have a name for it, but the expert blind spot, whatever you wanna call it.

Peter: They already knew, and they knew that would never work.

Dave: Right. You have an infrastructure in your mind, just like any company has infrastructure, and you have a blind spot that’s associated with what you can’t see because of what you know that just ain’t so, to go back to Mark Twain again.

In a big company, with all the tons of money and resources and capacity that a big organization has, it’s still easier to quit and start it in your garage than it is to innovate within that structure.

It’s mind-boggling ’cause companies pour tons of money into this. And they also buy companies and then destroy them. Like, they buy them without understanding their value.

I saw it at Business 2.0. It was a magazine. It was a very successful magazine in Silicon Valley. You guys might remember it.

It was bought by Time Inc. And they fired the sales force, and the sales force was the engine that ran that whole media business. The salespeople were basically selling into Silicon Valley, into the technology companies, and Time was like, “Oh well, we already have our sales force.”

They had a sales force of people that would go into Ford Motor Company and just basically take orders. They didn’t understand the industry. And so I watched, I had been working for the company as a consultant, like an illustrator, saw the company get bought.

You know, it’s like you buy a car and you take the engine out, and it was like watching it get thinner, and the bureaucracy blaming everything but themselves for the problem that they created.

And I think this happens a lot in business. But again, it’s that expert blind spot that gets in the way of seeing… And I think we each have it ourselves, too. It gets in the way of seeing what’s possible.

Jesse: Yeah. We’ve talked in the past about the work of the philosopher Thomas Kuhn. “The Structure of Scientific Revolutions” is this book where he introduced the concept of the paradigm shift to the popular discourse.

And when I think about what you’re talking about, when I think about these blind spots, I think about the risk of being trapped in an old paradigm, in an outdated paradigm that no longer applies.

And, for our audience, design leaders, I feel like this is a place where they just dwell in this absolute terror field of the Rumsfeldian unknown unknowns, the blind spot that by definition you don’t know is there. You can’t tell that something is being hidden from you by your own perspective because that’s what your perspective does. It filters your reality.

And I wonder what leaders need to do as they are simultaneously dealing with the pressures from executives in their organization, as well as the expectations of the people within their teams to escape that trap of the genuinely invisible blind spot.

How do you see those unknown unknowns?

Dave: I think one of the big unknown unknowns is just assuming that I’m gonna be in a corporation. I’m gonna be in a corporate job. Whether or not it’s the one that you’re in now, I think that those are the things that are most likely to be getting in your way.

Okay, so a design leader in a Fortune 500 company. That’s what I know how to do. Whatever I do, I’m gonna be a design leader in a Fortune 500 company, ’cause that’s how I understand the world. That’s what I know how to do.

What happens if there is not that role, there is no design leader in a Fortune 500 company in your future?

What happens if that role requires a whole different kind of person than you are? In some ways, a corporate job can be like a drug, like an addiction, and if you think about it, okay, addicts are usually not gonna give up voluntarily a drug until they hit some kind of a flat wall that they can’t continue to keep using it.

Jesse: Right. They’ve gotta hit bottom.

Dave: Yeah, so what is that for a lot of corporate leaders? It’s you get laid off at an age where you don’t have a lot of prospects.

And I think one thing, you know, it’s like death. You don’t wanna think about it, but it’s probably good to think about it. Do you have a do not resuscitate order? Have you got your will? You have life insurance? It’s not fun to think about your own death, and I think the same applies to your corporate death. Maybe it’s not fun to think about it but it’s wise to consider what your alternatives might be and to think about that realistically and say, Okay, let’s just say you’re not worried about your job today. That’s great. Maybe if you think about five years from now or 10 years from now, maybe there is something to worry about. What can you do? You could start saving money, number one, right? You could be more thoughtful about your expenses. You can be actually actively cultivating your social network outside of just your immediate colleagues and the people who can do something for you today.

You can start to actually think about your social safety net differently than just thinking about what is available to you inside your company.

Like one of the things I realized after selling my company was that I had a social network that I had invested a lot of time and energy in over many years. Many of those people became my customers when I decided to do Dave as a Service. There was a lot of people out there who had read my books or had been interested in something I had done and, when I was a corporate consultant, If you didn’t have at least $25,000, there was no point in us having a conversation ’cause there was nothing I could sell you, but there’s a lot of people who don’t have $25,000 to spend on a project who maybe I could provide some value to.

The corporate world is all about division of labor. And so we’ve become divided in some ways. The value proposition has gotten so splintered and divided that our value proposition is this tiny little role in this big machine. And, think about the user experience designer, the information architect trying to explain to the taxi driver what you do, right?

“Well, I design experience.” What does that mean? You know, and I think this is the case of a lot of corporate jobs. You can’t explain it to an average person in a restaurant or on the street. And the thing is, if you can’t explain it, that should be a big warning sign in the world that we’re in today.

Because what the jobs, I believe, of the future are gonna be, you have a role in a community, and you know your role.

It’s almost like going back to hunter-gatherer times. Everybody knew their role in their community. Everybody knew why they were useful, how they were useful or not. Everybody understood. If someone runs a Thai restaurant in your neighborhood, you don’t have to ask them to explain what they do. You know exactly what they do, and what they provide. It’s not something that is hard to understand or hard to explain, and I think a big part of what’s happening is all this kind of divided labor is stuff that can be more easily done by agents.

It’s the stuff that’s more tightly bundled, where the value proposition is not so easily automated, that is, about a role that you’re serving in a community, a usefulness.

In the article, I mentioned this friend of mine who runs a newspaper here. It’s a one-man newspaper. He’s been doing it for 40 years. AI’s not gonna take his job away. No way. He shows up at the community meetings. He knows people. They come to him with stories. He’s got advertisers. People write stories for him. He’s deeply interconnected with the community. Everybody understands the role that he plays in the community, and he understands the community.

So I feel like part of what’s gonna happen is, as we get more abstracted and we have more capabilities and powers, you’ll be able to do a lot of things without having to hire employees. And if you are in that corporate job, one thing I’d be thinking about is how do I think about this job not as something that I need to hang onto like a life raft, but something that can actually help be a vehicle for whatever I might wanna do next? And then take a more expansive perspective on what’s out there.

Dave: Like when I sat down to say, “What is Dave as a service?” There are a lot of things that did come up. People come to me when they lose their job. They come to me for advice on their career. People come to me asking for advice about writing books and publishing books and doing creative.

So there’s a lot of things that were happening that were not part of my corporate career, but they were in my life. They were in the background, and foregrounding those created a whole different kind of way of thinking about what I actually look like.

This is a question I think any corporate employee should be thinking about. If I were to be a service, you as a service, Peter as a service, Jesse as a service, and I had to do it all by myself without a team, what would that look like? What might that look like? What could I do that I could show up with, joyfully every day, even if it’s something simple as making sandwiches? What could I do that I could really enjoy that would connect me with a community?

Like my newspaper friend, it’s a local thing, but I don’t think a community has to be local in this day and age. And I think that’s what practice work, the shape of practice work is, and it’s older than history.

But whether you run a restaurant or whether you’re a tailor, you know your customers personally. And I think, how many people in a design leadership job in a Fortune 500 company can say they know their customers personally? It just would not be possible.

But I think we’re moving towards a future where you are gonna be required to articulate your value to the people who are actually paying your bills, the people who pay you. And they might not be your boss.

So I feel like the big skill that is gonna be required of all of us is learning how to create a customer. Both of you, I think, are very aware of that is a skill. That is a skill you can develop and that requires a way of thinking about how you show up in the world that’s very different from pleasing a boss to get a paycheck.

Jesse: It’s interesting to think about the implications of this for leaders of design teams inside organizations. So let’s say I don’t want to quit my job. Let’s say I love the leverage that comes with being able to make design decisions that touch literally millions of people every time we deploy.

If that is what’s exciting to me as a leader, then I am there to advocate for something else, which has to do with what design as a function contributes toward the value that we collectively create. And I’m there to stand for that contribution on my part and on the part of my team.

And, as you were talking, I find myself wondering about, how we define community, how we define the value that we create within community, and the shape of these evolving organizations, if it really does become, almost this gravitational pull away from hyper-specialization back toward a little bit more of a generalist kind of a value prop for people in these organizations.

But that generalist value prop is then built upon, as I hear you describe it, personal trust and a certain track record of value delivery. And that’s the means by which you get things done rather than rigidly defined areas of authority and hierarchical structures and things like that.

So then the challenge for the leader is not just to advocate for themselves, but also to advocate for the thing that they are there to spearhead and champion. Which, for us, for many years, it was human-centered design. All of us came into this work during a time when there was no voice of design anywhere in any kind of software development, and the software that we had was painful and difficult for people.

Dave: Yeah.

Jesse: And that gap presented a market opportunity, basically, that created this field.

And now I think there’s a new potential value proposition that design leaders have to advocate for, that doesn’t look like that anymore because it’s no longer about those things. And in fact, as you describe it, the organizational context itself is potentially shifting. Where your title on your business card doesn’t mean you get to make or influence certain decisions, right?

Dave: Yeah. So I was just reading about the guy who made the movie “El Mariachi,”

Jesse: Hmm. The great Robert Rodriguez.

Dave: Is that his name? Okay.

He went to Mexico and made a whole movie for $7,000, like a feature length film.

So this is the kind of thing that people in the film industry are like you can’t even make a trailer for less than $20,000.

And he had a film teacher who said, “No, you’re gonna need a, you need a…” He said, “I’m just gonna hold the camera myself,” you know? “And well, you need a director of photography. You need a…” And you learn the film industry by going and working on a film, and you see all different jobs, and you learn one or two jobs, and you grow in the industry that way.

Whereas he just said, “I’m gonna take a camera. I’m gonna tell a story. I’m gonna go take a camera to Mexico, and I’m gonna do this.” That was a successful movie, and he’s gone on to make other movies.

So that kind of mindset is, I think, what we’re gonna need more of in this AI age. Like, my brother worked at the FDA, and they’re a bottleneck because the people coming to propose different kinds of medical equipment and drugs and different things, they have such a long wait time because of the way they do it.

And I suggested like platform-type things like Kickstarter and other, kinda crowdsourcing, some of that. Because he worked for the government, he was so embedded in a way of thinking. The only way that he could think of to scale the pipeline was hire a lot more people, like triple in size.

Whereas now if you’re making movies the traditional way, you’re never gonna try and do something for $7,000. You wouldn’t even think to try that.

Whereas the potential of AI is that there are things that we just can’t even imagine are possible because of the way that we’ve done them before that are going to be possible. So the way you describe that design leader, “I’m someone who… I care about, I make the decisions, and we push a button and it impacts millions of people.”

Are you gonna need the corporation for that? Or could you do that? Jesse, you’ll be happy to know that the working title for that whole practice economy thing was “The Structure of Economic Revolutions,” which, ’cause it is kinda based on that whole Kuhn thing.

And we’ve had three of them in, the course of human history. One was agriculture, the second was manufacturing, and the one that’s happening now, that’s compressing now, is corporate work. When things get compressed, they don’t go away. We still have farming. We still have manufacturing. And we’re still gonna have corporations.

But the number of people required to run a farm, like one farmer, one person used to generate about five people’s food, like a family. Now one farmer generates about 100, 200 people’s worth of food. So it’s one person. They’re just like 50 times more effective.

And I think the same’s gonna be the case with a corporation. To be making the design decisions that you push the button and you affect the lives of thousands or millions of people, you may not need that corporate infrastructure to do that anymore.

You might be better off thinking like the El Mariachi guy. I’m sure there’s a lot he didn’t know that worked in his benefit, work to his favor. And so that’s where the beginner’s mind comes in, I think, is, what you don’t know that you don’t know, that can actually be your best friend, ’cause you don’t know that it’s not possible. You don’t know that it can’t be done. And so you have the temerity to go out and say maybe I can just do this.

Peter: I’m curious, as you were, years ago, researching liminal thinking, if the beginner’s mind thing came up then and what you saw. ‘ Cause, as you explained it earlier, the people you interviewed were under even greater constraint than anything we’re talking about here, right?

And so you were trying to figure out how do people who are under great constraint still do good work, work they’re proud of, make their way there? Was beginner’s mind part of it? And how do you tap into beginner’s mind when you’re already an expert, right?

Is there a way, like, my desire is, I want both. I want to be able to leverage my expertise, right? 30 years of hard-earned awareness. It’s not for nothin’. So, I, also am a service. I sometimes refer to myself as Peter as a service. And people come to Peter as a service for 30 years of expertise. That’s what they’re buying.

But in moments this, where assumptions probably are worth at least calling into question, I wouldn’t say dismiss them all, they’re all useless. In fact, I think some of that thinking is problematic. There’s plenty that we can take from prior experience into today that, if applied well, I think would make things easier.

But that aside, like, how to balance beginner’s mind, expert mind, and succeeding or, getting traction when you’re not in control of the situation, and it feels like you’re operating within someone else’s imposed structures?

Dave: It is a great question, and I believe I have a great answer. We’ll see what you think.

So when you hear new ideas, right? And you hear them all the time, right? Crazy ideas.

Generally speaking, the first evaluation criteria you have for a new idea is does it fit within what I already know? Does it make sense with what I already know? If it doesn’t make sense within what you already know, the tendency is to reject it and say, ” Okay that’s just an anomaly. That person was just lucky that happened.” And just basically find ways to reject it.

But the thing is, the new ideas that fit within what you already know, you’re not actually gonna learn anything dramatically new by accepting the stuff you already know. It’s the stuff that looks really strange, doesn’t make sense, I think you have to open up your aperture to be able to become aware of those.

So you’re gonna hear things that, you wanna reject it, because it actually challenges something you already know. That’s the stuff where you actually have the greatest potential to learn something new.

There was one that I just saw where it was like some guy started a whole AI company, I forget the name of the company, but he started it all by himself. He’s already making multiple, I think, millions of dollars on this company. He’s only one running it, and what it will do is you go there and it’ll make an AI company for you.

It’s like an AI company that makes AI companies.

That to me is mind-bogglingly weird. I think part of it is just learning to cultivate your curiosity about things that just either grate on you or just things that create that disconnect in your brain, that’s the stuff that’s actually most likely to generate some kind of new insight or learning, the stuff that you most automatically reject.

The story from “The Connected Company” book is the story of the American auto industry. They were like, “The Japanese are making these cars, and they’re so cheap.” And the first thing was the cars aren’t that great. And then they look at the cars. It takes them 10 years to figure out, oh, the cars are actually pretty good.

Then they go to Japan and they actually see the way that they’re making the cars, and people come back and they’re like, “Maybe that works in Japan, but it’ll never work here.”

And there’s all this stuff that they already knew about how to make cars that they couldn’t learn because they already knew.

And so even though they were getting all these signals for 20, 30, 40 years, it took them that long to actually recognize that there’s something happening there that, somehow people in Japan are able to make factories that make cars better and at half the price that we pay to do it, and it’s about the method and, like, lean manufacturing we call it now.

It’s like those expert blind spots. One way to start to mitigate for your expert blind spots is to start paying attention to stuff that you think that can’t be true. That’s the stuff that is most likely to generate some new insight for you, right? Because what if it is true?

Dave: There’s a thing that I talk about in my book called “acting as if,” which is, you don’t actually have to believe something, an idea is true or valid in order to test it. All you have to do is act as if it were true.

Let’s just say, take the example, Jesse, that you gave of the design leader who assumes that they have to be in the company to do the work that they wanna do.

You could also ask the question: What if I didn’t have the company behind me, and I wanted to do the same thing? What would that look like?

And you can act as if it were true, so act as if you didn’t even have the company or act as if you could do it for pennies on the dollar and see what happens.

The nice thing about acting as if is you can suspend your own disbelief about your own behavior. You can suspend your disbelief about anything long enough to try the experiment. You don’t even have to believe that it’s gonna work.

Jesse: Yeah.

Dave: You can act as if it were true. What if I only had $7,000 and had to make a movie and I wanted to do it, and I basically said, “It’s going to be a feature length film”?

Jesse: So I think part of what I hear you suggesting within all of this, and you’ve maybe touched on this a couple of times in this conversation, is the idea that really the whole software industry might look really different a few years from now than what we’ve become accustomed to up to this point.

Dave: I think it’s not just the software industry. The only thing in our world that doesn’t have a lot of competitive pressure on it is government, maybe healthcare, certain industries that are highly regulated, so they literally can’t innovate because there’s laws that keep them from innovating.

But everything else, AI is a really interesting to me technology.

I work with people on it, there’s people in my school who are working with AI, and I am too, and one thing that I’m noticing is that it’s the first tool that I’m aware of that actually can teach you how to use it.

And that’s incredibly interesting. And I’ve seen people go in a week or a month to where they’re talking about concepts that would not even have been intelligible to them a week ago.

The learning curve is rapid. People are making such rapid progress that I can’t even get them in a room to be able to even communicate with each other. They’re so widely distributed on this learning slope that once you get start on that journey, to find someone else who’s at your level is not that easy because people are progressing so rapidly.

I don’t think we can even try to make predictions, but I think what we can predict is it’s just not gonna look like what it looks like today. When the smartphone came along, I don’t think any of us really predicted the way that it was gonna change society.

Peter: Well,yeah, especially if you look at movies from pre-smartphone that, were trying to be future forward, they didn’t take it into account at all.

Dave: Yeah. We thought we were getting connected and we’re really getting more isolated. It’s almost like the opposite of what we thought.

Peter: But on that point actually, ’cause you were talking about Dave as a service. I’m Peter as a service. Jesse’s kind of Jesse as a service.

Jesse: I’m serviceable.

Peter: And while I appreciate the freedom that my independence affords me I have to admit that, I am seduced by the stability of that drug of corporatism that you were referring to before, right? To be independent, to be on your own, is a lot of hustle, a lot of uncertainty, a lot of trying to figure out what the market wants from you and when you do, the market changes and now you’re having to change, right? It’s not easy.

And we touched on this, Jesse and I did, in our last Liminal conversation, which is around kind of collective action, ’cause you’ve also talked about community. And I’m trying to understand how we operate as individuals, but not to be alone, right? ‘Cause I can feel quite lonely in my work, writing or whatever I’m doing.

And it’s nice I have clients, but I meet with them an hour here, an hour there. I don’t have a team that I’m doing stuff with, right? We’ve all been in environments where there was a team and we did stuff with the team and that was powerful, and we’ve all lost that.

I guess I’m just curious, Dave, how you’re dialing that size of productive unit. It doesn’t have to be a massive 300,000 person scaled organization, but is it really just gonna be a bunch of individuals, or, what are you foreseeing there?

Dave: This is just all speculation and intuition, but I find a lot of interest in the film and music industries. The music industry is a great one because you got a lot of solo artists who are also in bands or you got The Beatles, they started as a band and then they became independent artists.

You’ve got people like Willie Nelson, spent a lot of time with other bands, And I think there’s something about maybe thinking in terms of projects like that.

I’d like to believe that we’re moving towards a society where you could think of things in terms of projects and collaborations and have some kind of fluid movement between, being a solo artist and in a band.

What is a great band? They get together. They know each other. They have that chemistry. They can perform really. They know each other’s strengths and weaknesses. They balance each other really well. There’s something great about that.

And then there’s, we’ve all been in the team that’s dysfunctional, right? That’s like, “This is not a band that I wanna be in again.” So the project to me is a nice way to say, “Okay, if we really do a great album, and we really enjoyed the whole process, then we’ll stay together. We’ll do another one. We’ll do another one.” But for me if I start to think about looking towards the future, what does that look like, I think maybe projects, as opposed to companies.

And even if you look at the way that most companies operate they are projects even for serial entrepreneurs. There’s people who they’ll start a company. They grow it. They sell it. Maybe it was a company for the investors, but for them it was a project.

Jesse: So with all of this change and all of this transition and potential, what are you most looking forward to seeing unfold in the days to come?

Dave: We’re learning what the robots can do and what the computers can do, the computer can now kinda turn itself on, it can run itself, it can operate itself, we don’t have to be computer operators anymore.

And I think there’s something really liberating about that. I don’t think it’s gonna happen without pain and distress.

Not that we shouldn’t have been thinking about this for a long time, but we really ought to be thinking about universal healthcare. Because a lot of people are trapped in these organizations because our healthcare system is forcing that on them. And a lot of people, that’s a big barrier to them going off on their own, and that’s just a failure of our system. So there are some things that we can do to kinda ease the suffering, I think.

But what’s happening in the corporate world today is very similar to what happened in the factory and steel working and the mills and so forth. It’s undergoing a compression, I believe, and there’s gonna be displacement.

And I think as a society, we need to be thinking about how we make that transition easier for people. I think universal healthcare is kind of like a no-brainer. So many other countries have actually done it. But I look forward to what happens when people get on the other side of it.

Dave: We’re in this turbulence mode. It’s like we’re in the middle of a storm, and the storm’s gonna pass, and the waters are gonna get calm again, and we’re gonna see what’s on the other side of it.

Doesn’t mean there won’t be a lot of destruction, like Katrina kinda level destruction of our economy. I think that’s likely. And we’re in the middle of that storm right now, trying to cling to the rafters or, bailing water or just trying to do what we can do. We have this sense of this storm raging around us. We don’t know what is actually gonna be left or what’s gonna be destroyed or what buildings are gonna still be standing.

It makes sense to be in that mode, but I feel like there is gonna be another side, a calm after the storm, and I think it’s gonna be beautiful.

Peter: Wow.

Jesse: Dave Gray, thank you so much for being with us.

Dave: Thank you. Thanks for having me.

Peter: Yes. Thank you so much.

Jesse: Dave, if people wanna find you and your work on the internet, where can they do that?

Dave: schoolofthepossible.com.

Jesse: All right. Thanks again.

For more Finding Our Way, visit findingourway.design for past episodes and transcripts, or follow the show on LinkedIn. Visit petermerholz.com to find Peter’s newsletter, The Merholz Agenda, as well as Design Org Dimensions featuring his latest thinking and the actual tools he uses with clients.

If you’re looking for help with AI transformation or you just need a private advisor to help you solve your hardest leadership problems, visit my website at jessejamesgarrett.com to book your free one hour consultation.

If you’ve found value in something you’ve heard today, we hope you’ll pass this episode along to someone else who can use it. Thanks for everything you do for others, and thanks so much for listening.

In this episode, Peter and Jesse compare notes from on how AI is reshaping design teams. The conversation moves through the operational chaos of proliferating tools, the urgent need to articulate a value proposition, why design operations got cut right before they were needed most, and the window of expertise power that won’t stay open.
For more about Peter Merholz, his consulting, thought partnership, and teaching offerings: https://petermerholz.com/
For more about Jesse James Garrett, and his AI transformation and leadership coaching offerings: https://jessejamesgarrett.com/

Jesse: I’m Jesse James Garrett,

Peter: and I’m Peter Merholz.

Jesse: And we’re finding our way,

Peter: navigating the opportunities

Jesse: and challenges

Peter: of design and design leadership.

Jesse: On today’s show, Peter and I explore the emergent challenges of AI transformation for digital design teams. I’ll share insights from my seminar of the same name and compare notes with Peter on the larger trends we’re seeing. We’ll get into issues like renegotiating your cross-functional relationships and your value proposition, the cultural implications of running a team where everyone has their own custom tools, and just how long to hang on to people on your team who don’t want things to change.

Peter: Hello, Jesse.

Jesse: Hello, Peter.

Peter: What’s up?

Jesse: I thought it would be useful for us to get together and reflect a little bit on this last series of conversations that we’ve been having because for better or worse, there is one topic that is front and center in the minds of design leaders these days, and that is AI. How AI plays out in their products, how AI plays out on their teams, and how it impacts how design interfaces with the entire larger organization that it’s a part of.

Jesse: On this show, it has now been the better part of a year since this started dominating our conversations, going back to our conversation with Andrew Hogan back last August, talking about what he was finding out about AI adoption through his work leading research for Figma. Since then, we’ve talked with bunch of folks that are people who have been well-known to you and I for a long time.

People like Christian Crumlish, Christina Wodtke, Jorge Arango, Paul Ford, Dan Saffer. People who’ve been really immersed in this work for a while and who have seen this cycle turn a few times. And we have been talking with them about the ways in which this current cycle evokes and reminds them of the cycles of change that we’ve seen in the last 30 years or so.

And we’re also talking about how this time is different. And I’m curious where your thoughts have landed about those questions and what really genuinely is different this time? You know, Jorge brought up the idea that a lot of people are looking at this and questioning whether there’s a there there, you know.

And it has been reinforced through the conversations we’ve been having that, as Jorge put it, this is not a nothingburger. This is a burger.

Peter: Aha!

Jesse: And that has implications. And I’m wondering, reflecting on the last several months of these conversations for you what are the patterns that you think leaders need to be paying attention to as they are trying to guide their teams through this change?

Peter: You and I were part of a conversation last week that Jeffrey Veen instituted called the Design Futures Assembly, a half-day set of conversations and presentations on the intersection of AI and design, with some very heavy hitters in the room: OpenAI, Anthropic, Google, Microsoft, Figma, Adobe.

Also, I’m doing what I’m calling a listening tour of design executives trying to get a pulse check of what they’re thinking and feeling in this moment. And so I’m bringing that to bear. And it’s not a nothingburger. Definitely a burger.

And even if it was a nothingburger, the way people are acting, you can’t ignore it, right?

There’s something there. You have to, engage the…

Jesse: perception, if not the reality, right?

Peter: The perception and just the overwhelm or something, right? There’s just so much about it. You can’t ignore it. The thing is, what is it? I think it’s an interesting question.

And what I’m making of it, what we’re gonna definitely see, is how design operates will change. That is becoming truer, at least. That is changing.

I just had a conversation with a VP, we’ve heard variants of this story recently, where they have their own Git repo’s. They’re committing to prod, right? We’re collapsing the distance between the work of design and the work of development.

But there’s a potential risk when this happens, where when design gets associated with production, which has been the overwhelming mode for the last 15 years, the next step is to think you can automate design away because it’s more straightforward to automate production.

Peter: The conversation I had with this particular design leader was interesting to me because she has, well, three types of designers in her team.

Design strategists who were loving this. They’re able to imagine futures, visiontype, but do it in ways that feel more real. Quickly build things that you can put in front of users, get that user input, iterate. It’s just this unlock for these more strategic designers who are quite generalist in terms of strategy, research, content, design, to, with just one, maybe two of them, just do a lot more than they could have ever done before. So that’s at one end of the spectrum.

On the other end of the spectrum were designers on her team that also wanted to play with code, but maybe in the past couldn’t quite get there. They probably built their own prototypes and stuff in code. But now, with these tools and technology, they’re in code, they’re partnering directly with engineers. They’re able to kind of bleed into that realm. So it’s a different kind of generalism, right?

You have design strategy as more of this, let’s call it first diamond generalism, and I don’t know if she had a term for it, but let’s say the kind of design technologist as the second diamond design generalism.

And what she pointed out is, there is a population in the middle that’s getting lost. Like she wanted to make it clear that it’s not all wine and roses, that there is a population getting lost.

But something else that she did, actually, that I think you would appreciate based on the talk you gave last week about AI transformation. As it was becoming clear that AI was going to be important, she took two people on her team and turned them into a AI enablement squad. They got removed from their product work and their job was to figure out how this team was going to embrace AI, figure out the tooling, figure out matters of process, figure out how do you get repos, be the bridge to engineering, talk to them, understand what all those things are.

And that ended up spurring the creation, essentially, of this platform design team that’s dedicated to UX excellence. So if it’s not AI, it’s design systems. If it’s not design systems, it’s defining quality, right? She’s realized there’s a role there for this team, even beyond AI, to help set standards for how the team operates.

And I say that as a story. You know, it’s clear that the edges of design practice are blurring, and there’s a lot of opportunity for design to evolve and blur into those edges. And that is the part that, I think, is the burger, is navigating these adjacencies.

At least– It’s a big part of the burger for me.

Jesse: Yeah, I would say there are two things that stood out in what you talked about. Last week I did this online seminar that I called AI Transformation for Digital Design Teams, where I talk about the patterns and the strategies that I’ve been employing in my work as I’ve been helping teams and supporting leaders in developing strategies for tackling all of this stuff.

And you touched on a couple of things that I think are really key from what I’ve seen. First of all is, like you gotta clear the decks for somebody, whether that is leadership within your team, whether those are, again, like maybe the principal IC level might actually be a sweet spot where you can really offer an opportunity to people in the organization to leverage their hands-on skills in ways that can benefit a larger organization.

But if you don’t have the ability to clear the decks for people and get them engaged with a team like you’re describing, then to bring in a fractional leader from the outside, somebody like me, who can take a view of all of it and get it all organized for you, can really help to accelerate things.

The second piece of it, though, which I think is really key, is that the opportunity is not just to do what you’re already doing better. The opportunity is to take a step back and look at what design is and means for an organization and how this tooling can support that.

Jesse: And I think that the challenge and the opportunity for leaders is to apply a bit of a quality filter to all of this technology that’s being thrown at them and to ask themselves, “How is this supporting the value proposition that my team already has in place and/or How does this support the extension of my team’s value proposition towards something new, towards something bigger, and towards something that is maybe having more impact than we’ve ever had before?

Peter: You said the words value proposition. You said the phrase, “How do I use this to act upon the value proposition I already have in place?” It turns out, I would argue, most design teams haven’t articulated their value proposition…

Jesse: oh, sure. right?

Peter: I suspect it’s those teams that are having some of the biggest struggles right now, ’cause they don’t know to what end they would be adopting this.

It’s just whatever they’re doing, keep doing more of that faster, as opposed to this one leader that I was talking to, you know, there had been some strategic mandate, there had been desires for vision, there had been a recognition of how this group can be maybe more horizontal, looking across an end-to-end experience, while, you know, product and engineering is more vertical, focused on specific applications.

I was surprised how energized this leader was when I was talking to them about AI, but I think it was because they had conditions, right? They had the conditions in place to enable flourishing with these new tools and approaches.

Whereas I suspect most design organizations lack those conditions to enable that flourishing.

Jesse: Yeah. So one of the things that I called out in the talk that I did was just the fact that every company is gonna have its own unique path toward how this new tooling gets implemented, because every company is bringing its own legacy into it. The ways that things have been done in the past, the expectations have been placed on design teams in the past, the data structures, the decision-making structures, the organizational structures that constrain what’s possible within any given context.

And I think that’s a big piece of the task for leaders, is to figure out what’s actually gonna work here, as opposed to what works at the big companies in Silicon Valley or what works at the little startups in Silicon Valley or, you know, what’s working for our competitors or what is the standard that’s been set within our particular product category or industry segment.

But to ask ourselves based on what we have in place, because I think your point is right on. If you don’t know what your processes are It’s gonna be really hard to upgrade those processes in any kind of consistent way to incorporate this tooling. If you don’t know what your value proposition is, if you don’t know what the expectations are that your cross-functional partners are bringing to the table, you might be investing a whole bunch of energy in AI initiatives that have nothing to do with what is actually being asked of your teams.

And so for the leaders, the responsibility then becomes, again, to be this filter, to be the evaluator of where these investments make the most sense and deliver the most value and deliver the most impact both within the teams and cross-functionally.

Peter: You said something along the lines of every team charting their own unique path. You might call it an adaptive path.

Jesse: You might call it that, yes.

Peter: But, one of the risks, I think, of the direction that you’re suggesting, is that every organization starts building digital product differently.

In some ways, it sounds great. Purpose-built, totally bespoke, this process for this context, this company, this time, dial it right in and boom, they can just flow.

And that sounds good in some theory, but it doesn’t allow for mobility, interoperability, translation. And so if I’m a designer who’s working in a team that’s operating in its own unique way, and then I get reorged, and we know this happens all the time, and I’m now reorged into a team that operates totally differently, they charted their own unique path, now I have to spend a lot of time figuring out how I work there.

Whereas a year ago, by and large, design worked the same in most contexts. Used the same tools in roughly the same order.

One of the things we’re hearing now is not just the proliferation of AI-empowered tools that are out in the world, Figma with Figma Make, or Lovables and Cursors and Replits and v0s and Claudes and all that kind of stuff.

But I’m talking to design leaders who are like, “Oh, yeah, and we’re building tons of custom internal tools to solve problems that we have.” Which sure, ’cause of Claude, it’s relatively cheap and easy to build internal tools. But then you leave your company and you go to work for someone else, and they have a totally different internal tool suite that has nothing to do with the kind of internal tool suite you learned…

Jesse: right.

Peter: are you spending three months before you’re useful in this new context?

That doesn’t make sense to me, right?

And so I foresee some shaking out of some patterns, some stable patterns of ways of working, and input and output of tooling.

Jesse: I can see that. At the very least, I think that you have to have two things. You have to have consistent internal expectations just to be able to compare the work of different designers across the team and be able to evaluate who’s actually delivering and who is bringing a sophistication of craft to their work.

And then secondarily, there are those external expectations, your cross-functional expectations, your expectations at the executive and leadership levels, your expectations with your business owners that also have to be managed in here.

And you’ve touched on one of the big open questions, which is, like, how standard can it get while still embracing the inherent flexibility of the new tooling itself, which is literally a world where software costs nothing, a world where you don’t need to figure out how to build the custom tool.

You don’t have to get a developer’s time to build the custom tool. All you have to do is describe the outcome that you want, and a robot will make it for you. I think that fundamentally changes the role that software itself plays in people’s workflow.

Peter: We are in a very active period of discovery about exactly this, right? The more I think about it, the more I talk to folks about it, it’s not just about design when we’re talking about digital product.

It’s design connecting with product, connecting with engineering, possibly other teams, right? The workflow is not just one function, it’s a cross-functional workflow. And if, the design team has some combination of seven to 10 externally created tools plus 10 to 20 internally created tools that they’ve got going on, you could multiply that by all the other teams, and it starts getting out of hand.

But it’s a bit like that university landscape that was part of the inspiration for the name Adaptive Path, where, like, we’re seeing the paths people are laying down, and the ones that work are the ones that people continue to lay down, work on, and then we’re gonna pave those, right?

Those are probably the, some of the next big product opportunities.

Jesse: Mm-hmm.

Peter: There will probably be some shakeout where it’s not as rigid or as constrained as it had been a couple years ago where workflow processes were broadly assumed.

But I don’t foresee a chaotic future of ways of working ’cause that… I think there’ll just be too much organizational resistance to allow that to happen.

Jesse: Yeah. It’s not scalable in a couple of ways. It’s not scalable from an orchestration perspective, and it’s not scalable from an operational perspective. You know, this was the big question that I brought to the floor at the Design Futures Assembly last week. I was asking, what are the operational implications when every designer is creating their own flavor of prompt chain that helps them to get to a particular result?

How do you operationally assume or assure any kind of consistency across, especially across a very large team, where you’re potentially looking at, you know, there are teams out there of more than 1,000 people now, right? Design teams.

Peter: Yeah and for me, this is something I literally just wrote about earlier this week in a newsletter titled “The Overlooked Solution to AI Confusion.” That overlooked solution is design operations, right?

Jesse: Yeah.

Peter: I think a lot of teams wound down design operations,. I mean, I’ve literally had a conversation with a different company where I was talking to the lone remaining design operations person, whereas a few years ago there were four, now there’s one.

And I think that’s a pattern that happens in a lot of places, because starting in 2023, belt-tightening, do more with less, layoffs, whatever, it’s easy to let go of your operations people because they’re not builders. They’re not delivering direct value.

It turns out, though, that they are exactly… You know, your whole talk on AI transformation, which suggests in part a transformation team that sees the organization through, that transformation team is, you could call it an operational team. It’s not 100% operational, but 50% to 75% operational.

Jesse: It has a significant operational function, for sure. Yeah.

Peter: Yeah, when you talk about communication, coordination, planning, ways of working, those are all operational matters. Process improvement, tooling, those are all operational matters.

And it’s like we got rid of operations right before we needed them most.

Good work, everybody.

But, you never want operations to run things, and my ops friends might object to me saying that, but I believe it to be true.

And that becomes a problem, right? In agile transformations, you know, you bring in all the agile coaches, you bring on scrum masters, you bring on some flavor of program manager or whatever that assists with agile.

And now all of a sudden, no team can do anything until those operations folks have allowed it to happen, right?

That’s not what I’m talking about here, and I think that’s where a lot of antipathy towards operations comes, is what sometimes happens is operations shifts from being an enablement to a…

Jesse: compliance.

Peter: It becomes governance in and of itself, right? It’s not enabling governance across, it’s “We are the government.” Yeah, and that’s no go.

But any organization that’s going to effectively embrace these ways of working is either going to have to bring on operations folks or, to your point, retask individuals and give them an operations mandate for some period of time.

We were talking about prior models and there was this whole industry set up to support agile transformations, with, again, agile coaches and scrum masters and all this kind of stuff.

Which was good for a while, but then we kind of lost the plot, which was that those jobs were always meant to be temporary, until the teams could do it themselves. But, “temporary,” like, that’s just not a word that lands in most organizational contexts. And so you had these folks sticking around long past their due date.

And so, my thought here is, like, you need to set an expiration date.

Jesse: Yeah, I can’t remember which organizational thinker said that bureaucracies exist to sustain themselves, but that is basically the idea. That once you have roles in place they’re gonna seek ways to continue to make themselves relevant or prove that they should be relevant regardless of as you put it, their expiration date.

I think the challenge with that when it comes to AI is nobody can see the top of the mountain yet, you know? Nobody can actually see at what point we get to the other side. It is just climbing and climbing. And as the mandate for this foreseeable future is climbing, you’ve got to optimize for climbing the hill, moving into the unknown collectively as an organization, as a skill set for yourself as a leader and for your team as a collective.

Peter: So do we need AI sherpas?

Jesse: There is an element of that, for sure.

Peter: You were, you know, talking about one of the challenges with AI is we don’t know how high the mountain is. You could imagine there was a similar challenge… Like with agile transformation pretty soon we knew how high that mountain was. Turns out it was pretty fucking low.

But I could imagine, you know, if we had applied our way of thinking in the mid-’90s, we wouldn’t have known how high that original UX design mountain was, right? It took actually a number of years. In fact, we helped start a company in part to do the survey of the mountain, right? To figure out the shape of that.

And when we started Adaptive Path in 2001, user experience was already a thing for about five or six years, not broadly, but it existed. Now clearly AI has spread like wildfire in a way that UX did not back then. It can take a while to understand the shape of something.

Peter: I’m finding metaphors interesting right now, more interesting than I have in a while because I think they can give us some frames of reference, the blind men and the elephant, what is the shape of this thing, right? We’re all kind of picking at our part, but we’re having trouble seeing the whole.

I’m preparing a talk for an internal session right now, thinking about leadership in this moment. And I’ve got two metaphors that I’m currently playing with and both of which are about the act of setting conditions, right?

So I said earlier that setting conditions is kind of my frame of mode, right? I think we, when we think of design leadership, we tend to think of it as an active role of setting direction. This is what good looks like. This is quality. This is the vision. Let’s move toward that.

I’ve always believed design leadership has been more about setting conditions than delivering direction. I think that’s become irrefutable right now.

And I think what we’re seeing with AI is there’s just too much going on for any individual to set direction of.

So then if the challenge is to set conditions, create conditions, I’ve got two metaphors I’m working with.

One is that of a gardener, right? As a gardener, you are understanding your soil, understanding your sunlight, understanding your climate, so that’s the context setting. You are planting seeds. You have a vision for what you want in your garden. Is it gonna be a pretty flower garden? Is it gonna be a vegetable garden? Is it gonna be a bit of both? Is it gonna be landscape? So you have some vision of what you want.

You plant the seeds. You water or pray for rain. As things grow you encourage, you clip here, and you prune there, and you put up a trellis to get it to grow in that way, right?

But you’re never telling that one flower, “Be like this.” The flower knows what it’s going to be, but you’re creating the conditions to enable that garden to emerge in some way that you imagine… though possibly not, right? You know, there’s, I’m sure some improvisation in gardening. So that’s one metaphor.

The other is being an NBA head coach. And I think about this because it’s an analogy I used in the org design book, ’cause we talked about Steve Kerr. So before Steve Kerr joined the Warriors, good team, playoff team, but they never got past the second round. Steve Kerr joins the Warriors, pretty much the exact same players, and his first year, they win the championship.

He set a different set of conditions than the prior coach. He created a different operating model in terms of literally how they played on the court, but also how they worked behind the scenes. He brought joy. This is one of his kind of prevailing values, is joyfulness in work. And, you know, by changing the conditions for the same set of people, got a different and better outcome.

And the reason I think about head coaches, though, is, like, they’re not players. They’re not on the court. They’re not doing the thing. They’re trying to set it up, but then at some point you kind of have to step back and let the team make its way there.

The other reason I like the head coach analogy, is that we often tend to think that our design leaders have to be the best designer in the room. The head coach, Steve Kerr, was never better than the eighth or ninth best player on any team he ever played on. He was never the best player. He had played with Michael Jordan. He was far from being the best player, right?

And I think there’s something to remember that leaders don’t have to be the best practitioners. They have to be the best at getting the most out of those practitioners, and we lose sight of that, particularly in design.

Jesse: I think one thing that you touched on within this that I think is really important, and I think honestly cascades from the highest level decision-making all the way down to individual designers trying to deliver against individual requirements, which is that the introduction of this technology introduces an essential role of probability management on everybody involved.

That it’s no longer about perfect replicability and getting your systems so dialed in that you are getting exactly the same product off the assembly line every time, because that doesn’t play to the strengths of the technology. Playing to the strengths of the technology means creating space for variation.

It means creating the opportunity to pursue directions that might not actually ultimately work out. Which means that in a lot of cases, folks who came out of general assembly 10 years ago who were like, “Okay, here’s your tech stack and here’s your process, and now you can go get a job, and you can have this same set of expectations no matter where you land.” That stuff just straight up doesn’t apply anymore.

And the varying levels of maturity that you’re gonna see across these organizations are, in a lot of ways, going to be driven by the maturity of their leaders and the maturity of their expert-level practitioners who are going to provide that perspective that the leaders can’t get on their own.

Because to your point, they shouldn’t be knee-deep in the tools because they’ve got to be going to bat for the teams and what the teams need.

Peter: It’s funny though because… when you said that leaders shouldn’t be knee-deep in the tools, something I’m hearing from these design executives, not uniformly but mostly, is all of them feel like they do need to get into the tools in a way that they haven’t for the last, even, 10 years.

I talked to one leader who’s “Yeah, I never used Figma. I, you know, would go in there and make comments, but I couldn’t auto layout my way out of a paper bag. The last tool I used was Sketch or even Photoshop in terms of making designs, right?”

VPs who’ve had that mentality now are like, ” Oh, I gotta open up Claude Code. I gotta play with Lovable. I gotta build now in a way that I haven’t.” Which I find interesting, and I’m actually still coming to terms with that as someone who hasn’t been in the tools for a very long time.

Jesse: I think it’s necessary to be conversant with the technology in order to make informed judgments about how to deploy it. So as I talked about in the AI transformation talk, as I talk about with my clients, I think it is important for leaders to come to the table with a point of view on how this technology is best applied, where it really makes an impact, where it really makes a difference, and what we want to preserve of the human influence within these processes.

But I don’t think you can get there if you haven’t been at least a bit hands-on with it.

I guess that the thing is that I wouldn’t want leaders to think that their role is now kind of orchestrating this multi-variant operational condition-setting machine, because you can’t direct the design to the same degree that you used to be able to.

But you still have to provide for some variation and some context specificity within these design processes to enable designers to go their own way here and there, you know?

And that becomes a part of the organizational culture, that becomes a part of how people think about design.

Peter: Some of the people who are navigating this best are folks who’ve been around a while and who came up in early web, 1.0 in the mid to late ’90s. And I think it’s in part because that was also a bit of a Wild West. There was no, I heard the phrase for the first time last week, “go-to tech stack.”

There was no go-to tech stack. We didn’t really have a process. We were making it up as we went along. The technologies were variable. There was an explosion of tools. There was something similar in terms of that environment, but also from specifically a design standpoint, what’s interesting to me about this is there were those of us who were web native who recognized you could not lock down the presentation layer in a web browser.

But then I worked with many trained designers who all they wanted to do were put up giant GIFs because they wanted to maintain the typography and the color scheme and the brand and all that. And that’s not this medium. That’s a different medium, right?

And we got away from that, right? You know, by the early 2000s, those designers with their giant GIFs let go a bit. There were things like Flash that allowed maybe some tighter controls, but we were in a fluid area for a while.

And then I think essentially with probably these frameworks, your React- type frameworks, as well as just mobile design and development, for the last 15 or so years, we’ve gone back to, you know what, I, as the designer, can actually specify the pixel perfect experience that every customer is going to have in an identical fashion. I can lock that down.

And now to your point with AI, all that’s taken away if you wanna lean into this material, right?

One of the talks at the Design Futures Assembly was from Josh Clark and Veronica Kindred. They have a book called “Sentient Design,” and the mindset behind it is what does it mean when AI is the material?

And to your point, when AI is the material, it’s not something you lock down, right, going back to the gardening metaphor. It’s this thing that you’re like shaping some conditions and seeing what happens, and what happens might be better than what you could have predicted.

The last 10 to 15 years where as you said, you know, you could learn in a boot camp how to do this work. That was for a material and a mindset that we’re not in any more. in

Jesse: Doesn’t exist anymore. Yeah.

Peter: But the other thing that you said, you used the word orchestration, and that’s a word that I’ve been coming back to.

You gave a talk at an UX Week or something in 2008 or ’09, where you defined UX design as orchestration, right? Not detailed delivery, but how do I bring together all this stuff?

And I think design leadership is once again going to have to adopt an orchestrative mindset, not like a conductor necessarily, “You, that violin need to play that note in exactly that way,” but that there is this altitude that we’re operating at, a higher altitude of coordination of elements that are meant to work together, and the job of the designer is to influence that, shape it.

Not shape it like a sculptor, but nudge it. And also this is where the gardening metaphor comes back. There’s feedback loops, right? And you see something, and then you do a thing. You prune it here, you nudge it there, you do a thing. So it’s not always on shaping, it’s responding to the system as it evolves.

Jesse: You know, I have to say I am hearing the voice of one of our listeners, I don’t know who, but somebody out there who is thinking right now all of that is well and good, but I have no authority. The shape of my team’s work is basically constrained by the expectations of our cross-functional partners.

And all anybody is asking me about or looking for or talking about with regard to my team is delivery. And I think the question for somebody like that in that position is: How do you start to evolve both your team and the expectations around your team toward a different value proposition?

‘Cause it seems to me that’s what you’re suggesting, right? That a delivery-oriented team is going to have to find new ways to deliver value. Is that– Do I have that right?

Peter: Yes, either a delivery-oriented team is going to have to articulate a new value proposition or maybe, as we said earlier, articulate a value proposition. I think…

Jesse: to begin with, yeah.

Peter: many delivery-oriented teams have inherited their value proposition from their product leader or engineering leader or whomever they report to, as that’s the value they are delivering.

They’re gonna have to get out in front of and be intentional and mindful in the creation of a new value proposition.

You were asking earlier what’s new, what’s not. This is one of those what’s not, right? Like basics of leadership, and one of the basics of leadership is having a vision, having an agenda, having an idea of what is the change that you seek and articulating that, right?

And that doesn’t change just because it’s AI. You just need to apply that leadership practice to this moment.

What is the change you seek? If you’re a delivery-oriented org and you realize that you have two paths ahead of you.

Getting much smaller because much of that delivery can be handled by the robots. I was talking to someone who, their design systems team is turning into a UI infrastructure team, which is just gonna be in engineering. That’s just an engineering function now. It’s not even a design function. Maybe there’s some designers on the team, but they’re approaching it with an engineering mindset.

So that’s one path, and if you’re fine with that path, great. But if you’re not, then you need to articulate what change you seek, what potential you believe that you have in terms of positive impact within the organization you’re in that aligns with desired value as articulated by your leadership, and start doing the work of your team is delivering on that desired value.

Jesse: You know, one thing that has come up in my AI transformation work that I have heard from other folks as well that I think is a really important theme to consider in here is that everything that you’re describing assumes that the team is ready and willing to come right along with you and support that vision, you know?

And for a lot of designers, and honestly, I think it in some ways this afflicts the more junior designers more than the senior designers, although there are maybe different flavors of it, they don’t want this change. They don’t want different tools. They don’t want different processes. They don’t want to rethink their value proposition. They have the job that they wanted, you know?

And now you’re telling them that they don’t get to have it anymore. And so another thing that I think we’re gonna see, especially within design organizations, although we might see this more broadly beyond design, is a bit of a cultural schism between the people who are ready to embrace new tooling and the people who are pretty comfortable where they are and feel like they’re delivering plenty of value doing exactly what they’ve been doing.

And for leaders both from an operational as well as from a cultural perspective, they have to set a tone that is inclusive enough to cover that whole spectrum.

Peter: It has to be inclusive enough to cover the whole spectrum, but do you believe it is acceptable for some designers to remain intransigent?

Jesse: I think every organization is gonna reach that point by its own path. In some organizations, there’s gonna be a lot of tolerance for continuing to do things in old ways, you know? And it’s like that print shop that has that one computer back in the corner that still has the CRT because it’s the one that the guy who runs the shop trusts and knows how to use and doesn’t need anything different. And maybe everybody else around him is using some other kind of tooling to do their jobs.

But, I think you’re gonna see… kind of a long tail to this, where you’ll have a few organizations that are at the very front of the pack that are very aggressively in with the new, out with the old, churning their processes to arrive at some new patterns and some new paradigms and some new form of consistency.

Because I agree with you, It feels like we’ve gained too much, in the last 25 years, operational wisdom to just throw it all out because we’ve got new tools now.

But then I think, further down the tail, you’re gonna have a lot of organizations that are gonna live in this kind of hybrid space for a while, where there’ll be a few people who are embracing certain kinds of processes, and maybe other people in other parts of the organization for whom, you know, we only see an incremental gain from you taking up new tooling, and you’re doing perfectly fine as you are, and so we don’t need a new anything here.

And there are a lot of organizations that’ll be making that call probably for years to come, you know?

Peter: I find myself wondering about that if only because the conversations I’m having. So with this listening tour, when I talk to these VPs or chief design officers, if they’ve got, let’s say, 100 or fewer designers, all of them are expecting their entire teams to become IA-enabled. AI-enabled.

And in fact, one of the conversations I had today was with a design leader who’s like, “Yeah when it became clear that there were some folks who weren’t on the bus, they were shown the door.” Yep.

Jesse: I’m not saying that won’t happen and isn’t already happening, but based on the conversations I’ve been having, I’m not aware of a lot of organizations that have seen enough gain from new tooling, new processes to actually justify those kinds of cuts.

Usually, those kinds of cuts are coming about because they had other reasons. They had already overreached in their hiring in some meaningful way, and people are looking to this as almost like a preemptive strike to cut the team before it gets to a place where you’ve got a lot of extra people hanging around that you’re trying to figure out what to do with.

Peter: Yeah and as I say that, I’m not saying it because it’s what I want or necessarily what I think is right.

I’m just, thinking about these conversations, and I’m realizing that most of the design leaders I’m talking to are like, “Yeah, not only should my teams be AI-enabled, resistance to AI enablement is an indication that that person is probably not right for my org.”

Not even because they won’t use AI, but because it’s suggesting some incuriosity or intransigence or just some other kind of personality characteristic.

Jesse: Attachment to an identity, attachment to a kind of a craft.

Peter: Whereas I do think what you were talking about will likely persist in some organizations, but I suspect that in much the same way that every design team adopted Figma, were more than happy to get the hell out, first out of Photoshop and then out of Sketch, and they adopted Figma because they saw the value in it.

It probably them a little while. I’m sure there were teams that were like, “Wait, I don’t want PMs all up in my business.” In fact, I actually, as I’m saying that, I remember hearing designers saying, “I don’t want PMs all up in my business” right?

And that was the risk of Figma. “They’re gonna comment on my files.” But now it’s just an assumption and it’s fine. It’s fine.

And in fact, design was the entity that drove that adoption. Even now in organizations, you know, we have a shared friend, Z, the design ops leader, who’s like, “Yeah, my design team uses Figma less than product and marketing.” We drove the adoption, but now other teams actually see more value out of it.

I suspect that AI enablement will eventually be adopted in a similar way by design orgs. I don’t know exactly of what, but it will be seen as an absolute good. I’m sure there’ll be benefits and drawbacks, but in the calculus more benefits to drawbacks, and that any resistance to AI will be organizational, right?

So at the Design Futures Assembly, we had an old friend there who works at a giant bank, and he’s like, “In no way on planet Earth or throughout the galaxy will they ever let designers commit to prod at this bank. That is just not a thing that’s gonna happen.” Cybersecurity, info security, compliance, regulatory issues, et cetera, et cetera. The amount of effort it would take to get designers up to snuff for code- committing like that’s not worthwhile, right? That’s where it’s more likely for the constraints and barriers to be, than inborn of design practice.

Jesse: Yeah. And I think that’s part of the long tail effect that I was talking about. You know, each organization’s legacy and constraints are going to dictate where you fall on that tail in terms of how far toward new tooling you have permission to move, how much latitude you have cross-functionally as well as with your business stakeholders and people like policy and compliance and regulatory and all those kinds of things.

Different organizations are gonna find themselves in different places, and that’s why I think that this adaptivity ultimately ends up being not just a core skill for leaders to thrive, but a core skill for their entire teams to thrive as well.

And I can see, to your point about if they’re not curious about how to evolve their practices, let them go, right? This suggests that the culture of design teams going forward has to be one that is more experimental, that is more driven by individual inspiration and vision, that is more exploratory in finding new tooling, finding new techniques, finding their way to do this work.

Peter: It’s funny as you say that ’cause again, this feels like a throwback to me. I’m like, “Oh, 2003 called and wants its design profile back.” And I don’t disagree. The responsibility of the leader is to then make the space to allow that to happen, right?

‘Cause right now, I think a big reason for burnout and for anxiety and for whatever problems you see bleeding through spaces like LinkedIn or various design meetups is, even before AI, designers were overtaxed, spread too thin, supporting too many PMs, given too much to do, and as a result of a lot of that, found their value narrowed to a production or delivery mode, ’cause that’s the one kind of touchpoint between their work and the rest of the organization that people recognized as worthwhile.

And now, all of that is still true, and we’ve just layered on, “By the way, figure out this AI stuff. Peace be with you.” And they’re overwhelmed with which of these 15 tools do I use and in what combination? And this is your argument for AI transformation teams and practices and processes.

But like even when we get kind of over that hump, you know, this is a drum I’ve been beating for probably 25 years, which is how do we make work sane? When I was young and I worked in what I would now probably think of as moderately insane organizations, I was young and so I didn’t know any better, and I was willing to be insane.

And then, I was 28 when we started Adaptive Path, and one of the core operating principles of Adaptive Path was a sane working environment, right? That’s not necessarily what people outside the company understood. They thought it was about great user experience and…

Jesse: I’m not sure that’s what all our, people would agree that we created.

It was definitely an ambition.

Peter: You posted about the 25th anniversary. There were comments from Adaptive Pathers of days of yore who were like, “That was the best work environment I was ever in.” And that was something we were very explicit about creating, which was you can do great work without running yourself ragged, right?

And that, for some reason, is some revelation. It shouldn’t be. There’s no reason for most of these organizations that they operate the way they do, except that they don’t know any better or they just think in order to work, people have to be working 50, 60-hour weeks now.

They have to be always on. They have to be willing to respond to emails you know, nights and weekends and all this kind of stuff. And it’s like that doesn’t…

Jesse: 9-9-6, baby.

There’s

Peter: no evidence that 996 delivers better work, and in fact there’s evidence that it doesn’t. Evidence that, like, 35 to 40 hours a week turns out to be an optimal amount of effort. And when you ask people to work more than that, the quality of the work beyond that suffers such that then they have to work more to undo the bad work they did when they were overtaxed, right?

And so when you talk about experimentation and exploration, that requires leadership to fight for a sane working context that enables folks to do that kind of exploratory and experimental work.

Jesse: Yes. Yeah, I completely agree with you. In the talk, I refer to this as air cover.

Basically, this is the leader setting the context, both within their teams and again, cross-functionally and with the leadership about the ways in which their processes might not look like what they used to look like, and letting everybody know that you’re embracing a culture of adaptivity, and that’s gonna have consequences for how the team shows up.

One of the main reasons that I am advocating for design leaders to spin up these transformation teams and transformation initiatives is that by giving it this dedicated focus, by clearing the decks for a few people to really focus on driving these things, you can give it that extra level of attention that is not just about technology policy and not just about process, but about culture, about how the humans in the organization engage with the work, and what keeps those people engaged with the value that is actually being delivered by the larger team.

And in a lot of ways, what this is, is it’s not just about a culture of experimentation. It’s not just about a culture of exploration. It’s also about a culture of reflection and prioritization and a kind of ruthless evaluation of what’s working and what isn’t, so that you can scale those methods in meaningful ways.

And I don’t see how you can do that given the mandate of the leaders that most organizations already have in play, right? There’s just not enough space if you don’t dedicate somebody to it.

Peter: I was thinking about something Marty Cagan said at an internal presentation he gave at a company that was one of my clients. And this is a company that was trying to embrace a kind of product transformation, agile transformation. Not scrum transformation, but, let’s embrace dual track agile, let’s embrace product discovery, let’s build product the right way. What has kind of been conceived as the right way.

And the thing that Marty pointed out is that the single biggest constraint to that transformation does not come from product, design, and engineering. They do have to change how they work and there’s gonna be some resistance ’cause there’s always resistance to change.

But by and large, those teams get it. They’re like, “Yeah, we want to work this way ’cause we know what it unlocks.”

The biggest constraint to their ability to succeed is everyone else. And it’s how does finance think about funding models for teams? How does HR think about career pathing and performance evaluation and compensation for teams? How does sales and marketing engage with those teams from a, say, a requirements perspective? It’s all the other functions.

And what Marty pointed out is he had never seen a truly successful agile transformation or product transformation that didn’t involve the CEO. It needed the toppest down mandate of the CEO because the CEO could tell the non-product functions, ” Hey, you’re gonna have to change.”

But if the agile transformation was only being done from the CPO down, they’re gonna continue to behave as they have, and what’s gonna happen is kinda like a kudzu. You’re gonna clear the field briefly, and then over time, the practices of those other functions are gonna push back on product development.

And it might look agile. They’ll adopt agile rituals, but they’re gonna be behaving as they always have because of the larger forces at play. And so that’s to the point we were just making about experimentation and exploration. That’s the risk for AI transformations, is how are the rest of the organization reshaping their ways of working to enable that productively?

Jesse: And the leader’s gotta be managing those expectations, right? The leader has got to be the bridge between functions that helps those on both sides understand what each is bringing to the table, and what each can reasonably expect of the other so the politics doesn’t go away, you know?

Peter: No, the politics are as, if not more, politicky.

Though, it was funny, I had a conversation again today with a leader whose team is embracing AI and has AI enablement and there had been a top-down mandate. It wasn’t like metrics-driven. Like it wasn’t every team needs to use 20% AI or somewhat… You know, you hear about some of these arbitrary numbers in terms of AI application.

But there was a top-down mandate from the C-suite that teams need to be AI-enabled. And this leader’s like, “Okay, let’s figure that out,” and tasked folks to make that happen. One of the things that ended up happening is, because the way this leader approached it within their organization, they got out ahead of product. Design and engineering both took a similar approach in their realms and then partnered with one another.

And design got out ahead of product such that he who controls the prompt controls the product. Yeah, where design is starting to lead product strategy because they had demonstrated expertise in this area that was considered important right now and were able to leverage that for a kind of political gain.

That wasn’t the motivation, but that ended up being the byproduct. And as part of that, at least in my conversation with this leader, this is someone who used to have a seat at the table, and then that seat was taken away because of layering that occurred a year or two ago. And now they’re slowly creeping back to the table because of the team’s ability to do good work.

Jesse: Yes.

Peter: It’s delicate because you and I encourage leaders to recognize the politics in the organization they’re in. But the reason for this person’s success is they doubled down on, “My team is gonna work really well.” So it wasn’t political. It’s “How do I set them up to, make the most of this moment?”

And it turned out others recognized that and saw the value in it, and they didn’t have to manage up. They could just do the work really well. And I wonder if there’s something about this moment right now that you might not have to be as political if you can demonstrate capability. It’s a thought.

Jesse: Yeah, I think there’s potentially a lot less political legwork involved. But I will say that the political calculus for the leader is exactly the same, which is to understand the needs and the perspective of your various cross-functional partners as well as your business stakeholders and influencers, and make sure that stuff is represented in the choices that you’re making.

But yes, what you’re describing is exactly as it was foretold in days of yore. When I gave that talk last year, it was the pattern that I was seeing, if you got there first, you were gonna get that seat at the table.

Peter: I think about power dynamics and usually what’s considered the most powerful type of power within an organization is relational power, and that’s still largely true. But there are times where expertise power matters and we’re at one of those times. That if you can demonstrate expertise, people will listen to you.

That was not true three or four years ago. If your expertise was better Figma-ing or better knowledge of your users or whatever you were an expert in, that wasn’t interesting to the people around you, and so having that expertise did not really grant you influence. But…

Jesse: right.

Yeah.

Peter: If your expertise now is AI enablement and AI ability, people will lean in and go, “Oh, really? How are you doing it? How did you do that? Let’s talk. That’s interesting.” But this will be a window. At some point, it won’t be interesting that you’re an AI expert anymore.

Jesse: That’s true. Right.

Peter: Right?

But there’s an opportunity for design leaders to leverage this moment to get a bit ahead.

Jesse: Yeah. Time to take action.

Honestly, just in the six, eight months since we started having these conversations about this topic on this show in earnest, I think the conversation has significantly shifted and it’s time to go.

It’s time for leaders to really start to figure this out because they’re gonna get lapped if they don’t.

Peter: Yeah, and as I say that, I fear for further burnout on the part of our design leaders. Take care of yourselves too.

Jesse: Yeah, absolutely. Peter, thank you so much.

Peter: My pleasure, Jesse. Thank you for spurring this discussion.

Jesse: All right, see you soon.

For more Finding Our Way, visit findingourway.design for past episodes and transcripts, or follow the show on LinkedIn. Visit petermerholz.com to find Peter’s newsletter, The Merholz Agenda, as well as Design Org Dimensions featuring his latest thinking and the actual tools he uses with clients.

If you’re looking for help with AI transformation or you just need a private advisor to help you solve your hardest leadership problems, visit my website at jessejamesgarrett.com to book your free one hour consultation.

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Jesse: On today’s show, Peter and I explore the emergent challenges of AI transformation for digital design teams. I’ll share insights from my seminar of the same name and compare notes with Peter on the larger trends we’re seeing. We’ll get into issues like renegotiating your cross-functional relationships and your value proposition, the cultural implications of running a team where everyone has their own custom tools, and just how long to hang on to people on your team who don’t want things to change.

Peter: Hello, Jesse.

Jesse: Hello, Peter.

Peter: What’s up?

Jesse: I thought it would be useful for us to get together and reflect a little bit on this last series of conversations that we’ve been having because for better or worse, there is one topic that is front and center in the minds of design leaders these days, and that is AI. How AI plays out in their products, how AI plays out on their teams, and how it impacts how design interfaces with the entire larger organization that it’s a part of.

On this show, it has now been the better part of a year since this started dominating our conversations, going back to our conversation with Andrew Hogan back last August, talking about what he was finding out about AI adoption through his work leading research for Figma. Since then, we’ve talked with bunch of folks that are people who have been well-known to you and I for a long time.

People like Christian Crumlish, Christina Wodtke, Jorge Arango, Paul Ford, Dan Saffer. People who’ve been really immersed in this work for a while and who have seen this cycle turn a few times. And we have been talking with them about the ways in which this current cycle evokes and reminds them of the cycles of change that we’ve seen in the last 30 years or so.

And we’re also talking about how this time is different. And I’m curious where your thoughts have landed about those questions and what really genuinely is different this time? You know, Jorge brought up the idea that a lot of people are looking at this and questioning whether there’s a there there, you know.

And it has been reinforced through the conversations we’ve been having that, as Jorge put it, this is not a nothingburger. This is a burger.

Peter: Aha!

Jesse: And that has implications. And I’m wondering, reflecting on the last several months of these conversations for you what are the patterns that you think leaders need to be paying attention to as they are trying to guide their teams through this change?

Peter: You and I were part of a conversation last week that Jeffrey Veen instituted called the Design Futures Assembly, a half-day set of conversations and presentations on the intersection of AI and design, with some very heavy hitters in the room: OpenAI, Anthropic, Google, Microsoft, Figma, Adobe.

Also, I’m doing what I’m calling a listening tour of design executives trying to get a pulse check of what they’re thinking and feeling in this moment. And so I’m bringing that to bear. And it’s not a nothingburger. Definitely a burger.

And even if it was a nothingburger, the way people are acting, you can’t ignore it, right?

There’s something there. You have to, engage the…

Jesse: perception, if not the reality, right?

Peter: The perception and just the overwhelm or something, right? There’s just so much about it. You can’t ignore it. The thing is, what is it? I think it’s an interesting question.

And what I’m making of it, what we’re gonna definitely see, is how design operates will change. That is becoming truer, at least. That is changing.

I just had a conversation with a VP, we’ve heard variants of this story recently, where they have their own Git repo’s. They’re committing to prod, right? We’re collapsing the distance between the work of design and the work of development.

But there’s a potential risk when this happens, where when design gets associated with production, which has been the overwhelming mode for the last 15 years, the next step is to think you can automate design away because it’s more straightforward to automate production.

The conversation I had with this particular design leader was interesting to me because she has, well, three types of designers in her team.

Design strategists who were loving this. They’re able to imagine futures, visiontype, but do it in ways that feel more real. Quickly build things that you can put in front of users, get that user input, iterate. It’s just this unlock for these more strategic designers who are quite generalist in terms of strategy, research, content, design, to, with just one, maybe two of them, just do a lot more than they could have ever done before. So that’s at one end of the spectrum.

On the other end of the spectrum were designers on her team that also wanted to play with code, but maybe in the past couldn’t quite get there. They probably built their own prototypes and stuff in code. But now, with these tools and technology, they’re in code, they’re partnering directly with engineers. They’re able to kind of bleed into that realm. So it’s a different kind of generalism, right?

You have design strategy as more of this, let’s call it first diamond generalism, and I don’t know if she had a term for it, but let’s say the kind of design technologist as the second diamond design generalism.

And what she pointed out is, there is a population in the middle that’s getting lost. Like she wanted to make it clear that it’s not all wine and roses, that there is a population getting lost.

But something else that she did, actually, that I think you would appreciate based on the talk you gave last week about AI transformation. As it was becoming clear that AI was going to be important, she took two people on her team and turned them into a AI enablement squad. They got removed from their product work and their job was to figure out how this team was going to embrace AI, figure out the tooling, figure out matters of process, figure out how do you get repos, be the bridge to engineering, talk to them, understand what all those things are.

And that ended up spurring the creation, essentially, of this platform design team that’s dedicated to UX excellence. So if it’s not AI, it’s design systems. If it’s not design systems, it’s defining quality, right? She’s realized there’s a role there for this team, even beyond AI, to help set standards for how the team operates.

And I say that as a story. You know, it’s clear that the edges of design practice are blurring, and there’s a lot of opportunity for design to evolve and blur into those edges. And that is the part that, I think, is the burger, is navigating these adjacencies.

At least– It’s a big part of the burger for me.

Jesse: Yeah, I would say there are two things that stood out in what you talked about. Last week I did this online seminar that I called AI Transformation for Digital Design Teams, where I talk about the patterns and the strategies that I’ve been employing in my work as I’ve been helping teams and supporting leaders in developing strategies for tackling all of this stuff.

And you touched on a couple of things that I think are really key from what I’ve seen. First of all is, like you gotta clear the decks for somebody, whether that is leadership within your team, whether those are, again, like maybe the principal IC level might actually be a sweet spot where you can really offer an opportunity to people in the organization to leverage their hands-on skills in ways that can benefit a larger organization.

But if you don’t have the ability to clear the decks for people and get them engaged with a team like you’re describing, then to bring in a fractional leader from the outside, somebody like me, who can take a view of all of it and get it all organized for you, can really help to accelerate things.

The second piece of it, though, which I think is really key, is that the opportunity is not just to do what you’re already doing better. The opportunity is to take a step back and look at what design is and means for an organization and how this tooling can support that.

And I think that the challenge and the opportunity for leaders is to apply a bit of a quality filter to all of this technology that’s being thrown at them and to ask themselves, “How is this supporting the value proposition that my team already has in place and/or How does this support the extension of my team’s value proposition towards something new, towards something bigger, and towards something that is maybe having more impact than we’ve ever had before?

Peter: You said the words value proposition. You said the phrase, “How do I use this to act upon the value proposition I already have in place?” It turns out, I would argue, most design teams haven’t articulated their value proposition…

Jesse: oh, sure. right?

Peter: I suspect it’s those teams that are having some of the biggest struggles right now, ’cause they don’t know to what end they would be adopting this.

It’s just whatever they’re doing, keep doing more of that faster, as opposed to this one leader that I was talking to, you know, there had been some strategic mandate, there had been desires for vision, there had been a recognition of how this group can be maybe more horizontal, looking across an end-to-end experience, while, you know, product and engineering is more vertical, focused on specific applications.

I was surprised how energized this leader was when I was talking to them about AI, but I think it was because they had conditions, right? They had the conditions in place to enable flourishing with these new tools and approaches.

Whereas I suspect most design organizations lack those conditions to enable that flourishing.

Jesse: Yeah. So one of the things that I called out in the talk that I did was just the fact that every company is gonna have its own unique path toward how this new tooling gets implemented, because every company is bringing its own legacy into it. The ways that things have been done in the past, the expectations have been placed on design teams in the past, the data structures, the decision-making structures, the organizational structures that constrain what’s possible within any given context.

And I think that’s a big piece of the task for leaders, is to figure out what’s actually gonna work here, as opposed to what works at the big companies in Silicon Valley or what works at the little startups in Silicon Valley or, you know, what’s working for our competitors or what is the standard that’s been set within our particular product category or industry segment.

But to ask ourselves based on what we have in place, because I think your point is right on. If you don’t know what your processes are It’s gonna be really hard to upgrade those processes in any kind of consistent way to incorporate this tooling. If you don’t know what your value proposition is, if you don’t know what the expectations are that your cross-functional partners are bringing to the table, you might be investing a whole bunch of energy in AI initiatives that have nothing to do with what is actually being asked of your teams.

And so for the leaders, the responsibility then becomes, again, to be this filter, to be the evaluator of where these investments make the most sense and deliver the most value and deliver the most impact both within the teams and cross-functionally.

Peter: You said something along the lines of every team charting their own unique path. You might call it an adaptive path.

Jesse: You might call it that, yes.

Peter: But, one of the risks, I think, of the direction that you’re suggesting, is that every organization starts building digital product differently.

In some ways, it sounds great. Purpose-built, totally bespoke, this process for this context, this company, this time, dial it right in and boom, they can just flow.

And that sounds good in some theory, but it doesn’t allow for mobility, interoperability, translation. And so if I’m a designer who’s working in a team that’s operating in its own unique way, and then I get reorged, and we know this happens all the time, and I’m now reorged into a team that operates totally differently, they charted their own unique path, now I have to spend a lot of time figuring out how I work there.

Whereas a year ago, by and large, design worked the same in most contexts. Used the same tools in roughly the same order.

One of the things we’re hearing now is not just the proliferation of AI-empowered tools that are out in the world, Figma with Figma Make, or Lovables and Cursors and Replits and v0s and Claudes and all that kind of stuff.

But I’m talking to design leaders who are like, “Oh, yeah, and we’re building tons of custom internal tools to solve problems that we have.” Which sure, ’cause of Claude, it’s relatively cheap and easy to build internal tools. But then you leave your company and you go to work for someone else, and they have a totally different internal tool suite that has nothing to do with the kind of internal tool suite you learned…

Jesse: right.

Peter: are you spending three months before you’re useful in this new context?

That doesn’t make sense to me, right?

And so I foresee some shaking out of some patterns, some stable patterns of ways of working, and input and output of tooling.

Jesse: I can see that. At the very least, I think that you have to have two things. You have to have consistent internal expectations just to be able to compare the work of different designers across the team and be able to evaluate who’s actually delivering and who is bringing a sophistication of craft to their work.

And then secondarily, there are those external expectations, your cross-functional expectations, your expectations at the executive and leadership levels, your expectations with your business owners that also have to be managed in here.

And you’ve touched on one of the big open questions, which is, like, how standard can it get while still embracing the inherent flexibility of the new tooling itself, which is literally a world where software costs nothing, a world where you don’t need to figure out how to build the custom tool.

You don’t have to get a developer’s time to build the custom tool. All you have to do is describe the outcome that you want, and a robot will make it for you. I think that fundamentally changes the role that software itself plays in people’s workflow.

Peter: We are in a very active period of discovery about exactly this, right? The more I think about it, the more I talk to folks about it, it’s not just about design when we’re talking about digital product.

It’s design connecting with product, connecting with engineering, possibly other teams, right? The workflow is not just one function, it’s a cross-functional workflow. And if, the design team has some combination of seven to 10 externally created tools plus 10 to 20 internally created tools that they’ve got going on, you could multiply that by all the other teams, and it starts getting out of hand.

But it’s a bit like that university landscape that was part of the inspiration for the name Adaptive Path, where, like, we’re seeing the paths people are laying down, and the ones that work are the ones that people continue to lay down, work on, and then we’re gonna pave those, right?

Those are probably the, some of the next big product opportunities.

Jesse: Mm-hmm.

Peter: There will probably be some shakeout where it’s not as rigid or as constrained as it had been a couple years ago where workflow processes were broadly assumed.

But I don’t foresee a chaotic future of ways of working ’cause that… I think there’ll just be too much organizational resistance to allow that to happen.

Jesse: Yeah. It’s not scalable in a couple of ways. It’s not scalable from an orchestration perspective, and it’s not scalable from an operational perspective. You know, this was the big question that I brought to the floor at the Design Futures Assembly last week. I was asking, what are the operational implications when every designer is creating their own flavor of prompt chain that helps them to get to a particular result?

How do you operationally assume or assure any kind of consistency across, especially across a very large team, where you’re potentially looking at, you know, there are teams out there of more than 1,000 people now, right? Design teams.

Peter: Yeah and for me, this is something I literally just wrote about earlier this week in a newsletter titled “The Overlooked Solution to AI Confusion.” That overlooked solution is design operations, right?

Jesse: Yeah.

Peter: I think a lot of teams wound down design operations,. I mean, I’ve literally had a conversation with a different company where I was talking to the lone remaining design operations person, whereas a few years ago there were four, now there’s one.

And I think that’s a pattern that happens in a lot of places, because starting in 2023, belt-tightening, do more with less, layoffs, whatever, it’s easy to let go of your operations people because they’re not builders. They’re not delivering direct value.

It turns out, though, that they are exactly… You know, your whole talk on AI transformation, which suggests in part a transformation team that sees the organization through, that transformation team is, you could call it an operational team. It’s not 100% operational, but 50% to 75% operational.

Jesse: It has a significant operational function, for sure. Yeah.

Peter: Yeah, when you talk about communication, coordination, planning, ways of working, those are all operational matters. Process improvement, tooling, those are all operational matters.

And it’s like we got rid of operations right before we needed them most.

Good work, everybody.

But, you never want operations to run things, and my ops friends might object to me saying that, but I believe it to be true.

And that becomes a problem, right? In agile transformations, you know, you bring in all the agile coaches, you bring on scrum masters, you bring on some flavor of program manager or whatever that assists with agile.

And now all of a sudden, no team can do anything until those operations folks have allowed it to happen, right?

That’s not what I’m talking about here, and I think that’s where a lot of antipathy towards operations comes, is what sometimes happens is operations shifts from being an enablement to a…

Jesse: compliance.

Peter: It becomes governance in and of itself, right? It’s not enabling governance across, it’s “We are the government.” Yeah, and that’s no go.

But any organization that’s going to effectively embrace these ways of working is either going to have to bring on operations folks or, to your point, retask individuals and give them an operations mandate for some period of time.

We were talking about prior models and there was this whole industry set up to support agile transformations, with, again, agile coaches and scrum masters and all this kind of stuff.

Which was good for a while, but then we kind of lost the plot, which was that those jobs were always meant to be temporary, until the teams could do it themselves. But, “temporary,” like, that’s just not a word that lands in most organizational contexts. And so you had these folks sticking around long past their due date.

And so, my thought here is, like, you need to set an expiration date.

Jesse: Yeah, I can’t remember which organizational thinker said that bureaucracies exist to sustain themselves, but that is basically the idea. That once you have roles in place they’re gonna seek ways to continue to make themselves relevant or prove that they should be relevant regardless of as you put it, their expiration date.

I think the challenge with that when it comes to AI is nobody can see the top of the mountain yet, you know? Nobody can actually see at what point we get to the other side. It is just climbing and climbing. And as the mandate for this foreseeable future is climbing, you’ve got to optimize for climbing the hill, moving into the unknown collectively as an organization, as a skill set for yourself as a leader and for your team as a collective.

Peter: So do we need AI sherpas?

Jesse: There is an element of that, for sure.

Peter: You were, you know, talking about one of the challenges with AI is we don’t know how high the mountain is. You could imagine there was a similar challenge… Like with agile transformation pretty soon we knew how high that mountain was. Turns out it was pretty fucking low.

But I could imagine, you know, if we had applied our way of thinking in the mid-’90s, we wouldn’t have known how high that original UX design mountain was, right? It took actually a number of years. In fact, we helped start a company in part to do the survey of the mountain, right? To figure out the shape of that.

And when we started Adaptive Path in 2001, user experience was already a thing for about five or six years, not broadly, but it existed. Now clearly AI has spread like wildfire in a way that UX did not back then. It can take a while to understand the shape of something.

I’m finding metaphors interesting right now, more interesting than I have in a while because I think they can give us some frames of reference, the blind men and the elephant, what is the shape of this thing, right? We’re all kind of picking at our part, but we’re having trouble seeing the whole.

I’m preparing a talk for an internal session right now, thinking about leadership in this moment. And I’ve got two metaphors that I’m currently playing with and both of which are about the act of setting conditions, right?

So I said earlier that setting conditions is kind of my frame of mode, right? I think we, when we think of design leadership, we tend to think of it as an active role of setting direction. This is what good looks like. This is quality. This is the vision. Let’s move toward that.

I’ve always believed design leadership has been more about setting conditions than delivering direction. I think that’s become irrefutable right now.

And I think what we’re seeing with AI is there’s just too much going on for any individual to set direction of.

So then if the challenge is to set conditions, create conditions, I’ve got two metaphors I’m working with.

One is that of a gardener, right? As a gardener, you are understanding your soil, understanding your sunlight, understanding your climate, so that’s the context setting. You are planting seeds. You have a vision for what you want in your garden. Is it gonna be a pretty flower garden? Is it gonna be a vegetable garden? Is it gonna be a bit of both? Is it gonna be landscape? So you have some vision of what you want.

You plant the seeds. You water or pray for rain. As things grow you encourage, you clip here, and you prune there, and you put up a trellis to get it to grow in that way, right?

But you’re never telling that one flower, “Be like this.” The flower knows what it’s going to be, but you’re creating the conditions to enable that garden to emerge in some way that you imagine… though possibly not, right? You know, there’s, I’m sure some improvisation in gardening. So that’s one metaphor.

The other is being an NBA head coach. And I think about this because it’s an analogy I used in the org design book, ’cause we talked about Steve Kerr. So before Steve Kerr joined the Warriors, good team, playoff team, but they never got past the second round. Steve Kerr joins the Warriors, pretty much the exact same players, and his first year, they win the championship.

He set a different set of conditions than the prior coach. He created a different operating model in terms of literally how they played on the court, but also how they worked behind the scenes. He brought joy. This is one of his kind of prevailing values, is joyfulness in work. And, you know, by changing the conditions for the same set of people, got a different and better outcome.

And the reason I think about head coaches, though, is, like, they’re not players. They’re not on the court. They’re not doing the thing. They’re trying to set it up, but then at some point you kind of have to step back and let the team make its way there.

The other reason I like the head coach analogy, is that we often tend to think that our design leaders have to be the best designer in the room. The head coach, Steve Kerr, was never better than the eighth or ninth best player on any team he ever played on. He was never the best player. He had played with Michael Jordan. He was far from being the best player, right?

And I think there’s something to remember that leaders don’t have to be the best practitioners. They have to be the best at getting the most out of those practitioners, and we lose sight of that, particularly in design.

Jesse: I think one thing that you touched on within this that I think is really important, and I think honestly cascades from the highest level decision-making all the way down to individual designers trying to deliver against individual requirements, which is that the introduction of this technology introduces an essential role of probability management on everybody involved.

That it’s no longer about perfect replicability and getting your systems so dialed in that you are getting exactly the same product off the assembly line every time, because that doesn’t play to the strengths of the technology. Playing to the strengths of the technology means creating space for variation.

It means creating the opportunity to pursue directions that might not actually ultimately work out. Which means that in a lot of cases, folks who came out of general assembly 10 years ago who were like, “Okay, here’s your tech stack and here’s your process, and now you can go get a job, and you can have this same set of expectations no matter where you land.” That stuff just straight up doesn’t apply anymore.

And the varying levels of maturity that you’re gonna see across these organizations are, in a lot of ways, going to be driven by the maturity of their leaders and the maturity of their expert-level practitioners who are going to provide that perspective that the leaders can’t get on their own.

Because to your point, they shouldn’t be knee-deep in the tools because they’ve got to be going to bat for the teams and what the teams need.

Peter: It’s funny though because… when you said that leaders shouldn’t be knee-deep in the tools, something I’m hearing from these design executives, not uniformly but mostly, is all of them feel like they do need to get into the tools in a way that they haven’t for the last, even, 10 years.

I talked to one leader who’s “Yeah, I never used Figma. I, you know, would go in there and make comments, but I couldn’t auto layout my way out of a paper bag. The last tool I used was Sketch or even Photoshop in terms of making designs, right?”

VPs who’ve had that mentality now are like, ” Oh, I gotta open up Claude Code. I gotta play with Lovable. I gotta build now in a way that I haven’t.” Which I find interesting, and I’m actually still coming to terms with that as someone who hasn’t been in the tools for a very long time.

Jesse: I think it’s necessary to be conversant with the technology in order to make informed judgments about how to deploy it. So as I talked about in the AI transformation talk, as I talk about with my clients, I think it is important for leaders to come to the table with a point of view on how this technology is best applied, where it really makes an impact, where it really makes a difference, and what we want to preserve of the human influence within these processes.

But I don’t think you can get there if you haven’t been at least a bit hands-on with it.

I guess that the thing is that I wouldn’t want leaders to think that their role is now kind of orchestrating this multi-variant operational condition-setting machine, because you can’t direct the design to the same degree that you used to be able to.

But you still have to provide for some variation and some context specificity within these design processes to enable designers to go their own way here and there, you know?

And that becomes a part of the organizational culture, that becomes a part of how people think about design.

Peter: Some of the people who are navigating this best are folks who’ve been around a while and who came up in early web, 1.0 in the mid to late ’90s. And I think it’s in part because that was also a bit of a Wild West. There was no, I heard the phrase for the first time last week, “go-to tech stack.”

There was no go-to tech stack. We didn’t really have a process. We were making it up as we went along. The technologies were variable. There was an explosion of tools. There was something similar in terms of that environment, but also from specifically a design standpoint, what’s interesting to me about this is there were those of us who were web native who recognized you could not lock down the presentation layer in a web browser.

But then I worked with many trained designers who all they wanted to do were put up giant GIFs because they wanted to maintain the typography and the color scheme and the brand and all that. And that’s not this medium. That’s a different medium, right?

And we got away from that, right? You know, by the early 2000s, those designers with their giant GIFs let go a bit. There were things like Flash that allowed maybe some tighter controls, but we were in a fluid area for a while.

And then I think essentially with probably these frameworks, your React- type frameworks, as well as just mobile design and development, for the last 15 or so years, we’ve gone back to, you know what, I, as the designer, can actually specify the pixel perfect experience that every customer is going to have in an identical fashion. I can lock that down.

And now to your point with AI, all that’s taken away if you wanna lean into this material, right?

One of the talks at the Design Futures Assembly was from Josh Clark and Veronica Kindred. They have a book called “Sentient Design,” and the mindset behind it is what does it mean when AI is the material?

And to your point, when AI is the material, it’s not something you lock down, right, going back to the gardening metaphor. It’s this thing that you’re like shaping some conditions and seeing what happens, and what happens might be better than what you could have predicted.

The last 10 to 15 years where as you said, you know, you could learn in a boot camp how to do this work. That was for a material and a mindset that we’re not in any more. in

Jesse: Doesn’t exist anymore. Yeah.

Peter: But the other thing that you said, you used the word orchestration, and that’s a word that I’ve been coming back to.

You gave a talk at an UX Week or something in 2008 or ’09, where you defined UX design as orchestration, right? Not detailed delivery, but how do I bring together all this stuff?

And I think design leadership is once again going to have to adopt an orchestrative mindset, not like a conductor necessarily, “You, that violin need to play that note in exactly that way,” but that there is this altitude that we’re operating at, a higher altitude of coordination of elements that are meant to work together, and the job of the designer is to influence that, shape it.

Not shape it like a sculptor, but nudge it. And also this is where the gardening metaphor comes back. There’s feedback loops, right? And you see something, and then you do a thing. You prune it here, you nudge it there, you do a thing. So it’s not always on shaping, it’s responding to the system as it evolves.

Jesse: You know, I have to say I am hearing the voice of one of our listeners, I don’t know who, but somebody out there who is thinking right now all of that is well and good, but I have no authority. The shape of my team’s work is basically constrained by the expectations of our cross-functional partners.

And all anybody is asking me about or looking for or talking about with regard to my team is delivery. And I think the question for somebody like that in that position is: How do you start to evolve both your team and the expectations around your team toward a different value proposition?

‘Cause it seems to me that’s what you’re suggesting, right? That a delivery-oriented team is going to have to find new ways to deliver value. Is that– Do I have that right?

Peter: Yes, either a delivery-oriented team is going to have to articulate a new value proposition or maybe, as we said earlier, articulate a value proposition. I think…

Jesse: to begin with, yeah.

Peter: many delivery-oriented teams have inherited their value proposition from their product leader or engineering leader or whomever they report to, as that’s the value they are delivering.

They’re gonna have to get out in front of and be intentional and mindful in the creation of a new value proposition.

You were asking earlier what’s new, what’s not. This is one of those what’s not, right? Like basics of leadership, and one of the basics of leadership is having a vision, having an agenda, having an idea of what is the change that you seek and articulating that, right?

And that doesn’t change just because it’s AI. You just need to apply that leadership practice to this moment.

What is the change you seek? If you’re a delivery-oriented org and you realize that you have two paths ahead of you.

Getting much smaller because much of that delivery can be handled by the robots. I was talking to someone who, their design systems team is turning into a UI infrastructure team, which is just gonna be in engineering. That’s just an engineering function now. It’s not even a design function. Maybe there’s some designers on the team, but they’re approaching it with an engineering mindset.

So that’s one path, and if you’re fine with that path, great. But if you’re not, then you need to articulate what change you seek, what potential you believe that you have in terms of positive impact within the organization you’re in that aligns with desired value as articulated by your leadership, and start doing the work of your team is delivering on that desired value.

Jesse: You know, one thing that has come up in my AI transformation work that I have heard from other folks as well that I think is a really important theme to consider in here is that everything that you’re describing assumes that the team is ready and willing to come right along with you and support that vision, you know?

And for a lot of designers, and honestly, I think it in some ways this afflicts the more junior designers more than the senior designers, although there are maybe different flavors of it, they don’t want this change. They don’t want different tools. They don’t want different processes. They don’t want to rethink their value proposition. They have the job that they wanted, you know?

And now you’re telling them that they don’t get to have it anymore. And so another thing that I think we’re gonna see, especially within design organizations, although we might see this more broadly beyond design, is a bit of a cultural schism between the people who are ready to embrace new tooling and the people who are pretty comfortable where they are and feel like they’re delivering plenty of value doing exactly what they’ve been doing.

And for leaders both from an operational as well as from a cultural perspective, they have to set a tone that is inclusive enough to cover that whole spectrum.

Peter: It has to be inclusive enough to cover the whole spectrum, but do you believe it is acceptable for some designers to remain intransigent?

Jesse: I think every organization is gonna reach that point by its own path. In some organizations, there’s gonna be a lot of tolerance for continuing to do things in old ways, you know? And it’s like that print shop that has that one computer back in the corner that still has the CRT because it’s the one that the guy who runs the shop trusts and knows how to use and doesn’t need anything different. And maybe everybody else around him is using some other kind of tooling to do their jobs.

But, I think you’re gonna see… kind of a long tail to this, where you’ll have a few organizations that are at the very front of the pack that are very aggressively in with the new, out with the old, churning their processes to arrive at some new patterns and some new paradigms and some new form of consistency.

Because I agree with you, It feels like we’ve gained too much, in the last 25 years, operational wisdom to just throw it all out because we’ve got new tools now.

But then I think, further down the tail, you’re gonna have a lot of organizations that are gonna live in this kind of hybrid space for a while, where there’ll be a few people who are embracing certain kinds of processes, and maybe other people in other parts of the organization for whom, you know, we only see an incremental gain from you taking up new tooling, and you’re doing perfectly fine as you are, and so we don’t need a new anything here.

And there are a lot of organizations that’ll be making that call probably for years to come, you know?

Peter: I find myself wondering about that if only because the conversations I’m having. So with this listening tour, when I talk to these VPs or chief design officers, if they’ve got, let’s say, 100 or fewer designers, all of them are expecting their entire teams to become IA-enabled. AI-enabled.

And in fact, one of the conversations I had today was with a design leader who’s like, “Yeah when it became clear that there were some folks who weren’t on the bus, they were shown the door.” Yep.

Jesse: I’m not saying that won’t happen and isn’t already happening, but based on the conversations I’ve been having, I’m not aware of a lot of organizations that have seen enough gain from new tooling, new processes to actually justify those kinds of cuts.

Usually, those kinds of cuts are coming about because they had other reasons. They had already overreached in their hiring in some meaningful way, and people are looking to this as almost like a preemptive strike to cut the team before it gets to a place where you’ve got a lot of extra people hanging around that you’re trying to figure out what to do with.

Peter: Yeah and as I say that, I’m not saying it because it’s what I want or necessarily what I think is right.

I’m just, thinking about these conversations, and I’m realizing that most of the design leaders I’m talking to are like, “Yeah, not only should my teams be AI-enabled, resistance to AI enablement is an indication that that person is probably not right for my org.”

Not even because they won’t use AI, but because it’s suggesting some incuriosity or intransigence or just some other kind of personality characteristic.

Jesse: Attachment to an identity, attachment to a kind of a craft.

Peter: Whereas I do think what you were talking about will likely persist in some organizations, but I suspect that in much the same way that every design team adopted Figma, were more than happy to get the hell out, first out of Photoshop and then out of Sketch, and they adopted Figma because they saw the value in it.

It probably them a little while. I’m sure there were teams that were like, “Wait, I don’t want PMs all up in my business.” In fact, I actually, as I’m saying that, I remember hearing designers saying, “I don’t want PMs all up in my business” right?

And that was the risk of Figma. “They’re gonna comment on my files.” But now it’s just an assumption and it’s fine. It’s fine.

And in fact, design was the entity that drove that adoption. Even now in organizations, you know, we have a shared friend, Z, the design ops leader, who’s like, “Yeah, my design team uses Figma less than product and marketing.” We drove the adoption, but now other teams actually see more value out of it.

I suspect that AI enablement will eventually be adopted in a similar way by design orgs. I don’t know exactly of what, but it will be seen as an absolute good. I’m sure there’ll be benefits and drawbacks, but in the calculus more benefits to drawbacks, and that any resistance to AI will be organizational, right?

So at the Design Futures Assembly, we had an old friend there who works at a giant bank, and he’s like, “In no way on planet Earth or throughout the galaxy will they ever let designers commit to prod at this bank. That is just not a thing that’s gonna happen.” Cybersecurity, info security, compliance, regulatory issues, et cetera, et cetera. The amount of effort it would take to get designers up to snuff for code- committing like that’s not worthwhile, right? That’s where it’s more likely for the constraints and barriers to be, than inborn of design practice.

Jesse: Yeah. And I think that’s part of the long tail effect that I was talking about. You know, each organization’s legacy and constraints are going to dictate where you fall on that tail in terms of how far toward new tooling you have permission to move, how much latitude you have cross-functionally as well as with your business stakeholders and people like policy and compliance and regulatory and all those kinds of things.

Different organizations are gonna find themselves in different places, and that’s why I think that this adaptivity ultimately ends up being not just a core skill for leaders to thrive, but a core skill for their entire teams to thrive as well.

And I can see, to your point about if they’re not curious about how to evolve their practices, let them go, right? This suggests that the culture of design teams going forward has to be one that is more experimental, that is more driven by individual inspiration and vision, that is more exploratory in finding new tooling, finding new techniques, finding their way to do this work.

Peter: It’s funny as you say that ’cause again, this feels like a throwback to me. I’m like, “Oh, 2003 called and wants its design profile back.” And I don’t disagree. The responsibility of the leader is to then make the space to allow that to happen, right?

‘Cause right now, I think a big reason for burnout and for anxiety and for whatever problems you see bleeding through spaces like LinkedIn or various design meetups is, even before AI, designers were overtaxed, spread too thin, supporting too many PMs, given too much to do, and as a result of a lot of that, found their value narrowed to a production or delivery mode, ’cause that’s the one kind of touchpoint between their work and the rest of the organization that people recognized as worthwhile.

And now, all of that is still true, and we’ve just layered on, “By the way, figure out this AI stuff. Peace be with you.” And they’re overwhelmed with which of these 15 tools do I use and in what combination? And this is your argument for AI transformation teams and practices and processes.

But like even when we get kind of over that hump, you know, this is a drum I’ve been beating for probably 25 years, which is how do we make work sane? When I was young and I worked in what I would now probably think of as moderately insane organizations, I was young and so I didn’t know any better, and I was willing to be insane.

And then, I was 28 when we started Adaptive Path, and one of the core operating principles of Adaptive Path was a sane working environment, right? That’s not necessarily what people outside the company understood. They thought it was about great user experience and…

Jesse: I’m not sure that’s what all our, people would agree that we created.

It was definitely an ambition.

Peter: You posted about the 25th anniversary. There were comments from Adaptive Pathers of days of yore who were like, “That was the best work environment I was ever in.” And that was something we were very explicit about creating, which was you can do great work without running yourself ragged, right?

And that, for some reason, is some revelation. It shouldn’t be. There’s no reason for most of these organizations that they operate the way they do, except that they don’t know any better or they just think in order to work, people have to be working 50, 60-hour weeks now.

They have to be always on. They have to be willing to respond to emails you know, nights and weekends and all this kind of stuff. And it’s like that doesn’t…

Jesse: 9-9-6, baby.

There’s

Peter: no evidence that 996 delivers better work, and in fact there’s evidence that it doesn’t. Evidence that, like, 35 to 40 hours a week turns out to be an optimal amount of effort. And when you ask people to work more than that, the quality of the work beyond that suffers such that then they have to work more to undo the bad work they did when they were overtaxed, right?

And so when you talk about experimentation and exploration, that requires leadership to fight for a sane working context that enables folks to do that kind of exploratory and experimental work.

Jesse: Yes. Yeah, I completely agree with you. In the talk, I refer to this as air cover.

Basically, this is the leader setting the context, both within their teams and again, cross-functionally and with the leadership about the ways in which their processes might not look like what they used to look like, and letting everybody know that you’re embracing a culture of adaptivity, and that’s gonna have consequences for how the team shows up.

One of the main reasons that I am advocating for design leaders to spin up these transformation teams and transformation initiatives is that by giving it this dedicated focus, by clearing the decks for a few people to really focus on driving these things, you can give it that extra level of attention that is not just about technology policy and not just about process, but about culture, about how the humans in the organization engage with the work, and what keeps those people engaged with the value that is actually being delivered by the larger team.

And in a lot of ways, what this is, is it’s not just about a culture of experimentation. It’s not just about a culture of exploration. It’s also about a culture of reflection and prioritization and a kind of ruthless evaluation of what’s working and what isn’t, so that you can scale those methods in meaningful ways.

And I don’t see how you can do that given the mandate of the leaders that most organizations already have in play, right? There’s just not enough space if you don’t dedicate somebody to it.

Peter: I was thinking about something Marty Cagan said at an internal presentation he gave at a company that was one of my clients. And this is a company that was trying to embrace a kind of product transformation, agile transformation. Not scrum transformation, but, let’s embrace dual track agile, let’s embrace product discovery, let’s build product the right way. What has kind of been conceived as the right way.

And the thing that Marty pointed out is that the single biggest constraint to that transformation does not come from product, design, and engineering. They do have to change how they work and there’s gonna be some resistance ’cause there’s always resistance to change.

But by and large, those teams get it. They’re like, “Yeah, we want to work this way ’cause we know what it unlocks.”

The biggest constraint to their ability to succeed is everyone else. And it’s how does finance think about funding models for teams? How does HR think about career pathing and performance evaluation and compensation for teams? How does sales and marketing engage with those teams from a, say, a requirements perspective? It’s all the other functions.

And what Marty pointed out is he had never seen a truly successful agile transformation or product transformation that didn’t involve the CEO. It needed the toppest down mandate of the CEO because the CEO could tell the non-product functions, ” Hey, you’re gonna have to change.”

But if the agile transformation was only being done from the CPO down, they’re gonna continue to behave as they have, and what’s gonna happen is kinda like a kudzu. You’re gonna clear the field briefly, and then over time, the practices of those other functions are gonna push back on product development.

And it might look agile. They’ll adopt agile rituals, but they’re gonna be behaving as they always have because of the larger forces at play. And so that’s to the point we were just making about experimentation and exploration. That’s the risk for AI transformations, is how are the rest of the organization reshaping their ways of working to enable that productively?

Jesse: And the leader’s gotta be managing those expectations, right? The leader has got to be the bridge between functions that helps those on both sides understand what each is bringing to the table, and what each can reasonably expect of the other so the politics doesn’t go away, you know?

Peter: No, the politics are as, if not more, politicky.

Though, it was funny, I had a conversation again today with a leader whose team is embracing AI and has AI enablement and there had been a top-down mandate. It wasn’t like metrics-driven. Like it wasn’t every team needs to use 20% AI or somewhat… You know, you hear about some of these arbitrary numbers in terms of AI application.

But there was a top-down mandate from the C-suite that teams need to be AI-enabled. And this leader’s like, “Okay, let’s figure that out,” and tasked folks to make that happen. One of the things that ended up happening is, because the way this leader approached it within their organization, they got out ahead of product. Design and engineering both took a similar approach in their realms and then partnered with one another.

And design got out ahead of product such that he who controls the prompt controls the product. Yeah, where design is starting to lead product strategy because they had demonstrated expertise in this area that was considered important right now and were able to leverage that for a kind of political gain.

That wasn’t the motivation, but that ended up being the byproduct. And as part of that, at least in my conversation with this leader, this is someone who used to have a seat at the table, and then that seat was taken away because of layering that occurred a year or two ago. And now they’re slowly creeping back to the table because of the team’s ability to do good work.

Jesse: Yes.

Peter: It’s delicate because you and I encourage leaders to recognize the politics in the organization they’re in. But the reason for this person’s success is they doubled down on, “My team is gonna work really well.” So it wasn’t political. It’s “How do I set them up to, make the most of this moment?”

And it turned out others recognized that and saw the value in it, and they didn’t have to manage up. They could just do the work really well. And I wonder if there’s something about this moment right now that you might not have to be as political if you can demonstrate capability. It’s a thought.

Jesse: Yeah, I think there’s potentially a lot less political legwork involved. But I will say that the political calculus for the leader is exactly the same, which is to understand the needs and the perspective of your various cross-functional partners as well as your business stakeholders and influencers, and make sure that stuff is represented in the choices that you’re making.

But yes, what you’re describing is exactly as it was foretold in days of yore. When I gave that talk last year, it was the pattern that I was seeing, if you got there first, you were gonna get that seat at the table.

Peter: I think about power dynamics and usually what’s considered the most powerful type of power within an organization is relational power, and that’s still largely true. But there are times where expertise power matters and we’re at one of those times. That if you can demonstrate expertise, people will listen to you.

That was not true three or four years ago. If your expertise was better Figma-ing or better knowledge of your users or whatever you were an expert in, that wasn’t interesting to the people around you, and so having that expertise did not really grant you influence. But…

Jesse: right.

Yeah.

Peter: If your expertise now is AI enablement and AI ability, people will lean in and go, “Oh, really? How are you doing it? How did you do that? Let’s talk. That’s interesting.” But this will be a window. At some point, it won’t be interesting that you’re an AI expert anymore.

Jesse: That’s true. Right.

Peter: Right?

But there’s an opportunity for design leaders to leverage this moment to get a bit ahead.

Jesse: Yeah. Time to take action.

Honestly, just in the six, eight months since we started having these conversations about this topic on this show in earnest, I think the conversation has significantly shifted and it’s time to go.

It’s time for leaders to really start to figure this out because they’re gonna get lapped if they don’t.

Peter: Yeah, and as I say that, I fear for further burnout on the part of our design leaders. Take care of yourselves too.

Jesse: Yeah, absolutely. Peter, thank you so much.

Peter: My pleasure, Jesse. Thank you for spurring this discussion.

Jesse: All right, see you soon.

For more Finding Our Way, visit findingourway.design for past episodes and transcripts, or follow the show on LinkedIn. Visit petermerholz.com to find Peter’s newsletter, The Merholz Agenda, as well as Design Org Dimensions featuring his latest thinking and the actual tools he uses with clients.

If you’re looking for help with AI transformation or you just need a private advisor to help you solve your hardest leadership problems, visit my website at jessejamesgarrett.com to book your free one hour consultation.

If you’ve found value in something you’ve heard today, we hope you’ll pass this episode along to someone else who can use it. Thanks for everything you do for others, and thanks so much for listening.

Journalist, technologist, and Aboard co-founder Paul Ford joins Peter and Jesse with the perspective of someone running a services firm in the middle of being remade by AI. The conversation covers the collapsing cost of software, blurring roles, what machines do well and badly, what design’s value proposition becomes, and Paul’s practical advice for staying upright through indefinite change.
Paul’s company: https://aboard.com/; Paul’s LinkedIn: https://www.linkedin.com/in/ftrain/
Peter’s website: https://petermerholz.com/
Jesse’s website: https://jessejamesgarrett.com/

Jesse: I’m Jesse James Garrett,

Peter: and I’m Peter Merholz.

Jesse: And we’re finding our way,

Peter: navigating the opportunities

Jesse: and challenges

Peter: of design and design leadership.

Jesse: On today’s show, journalist, technologist, and agency founder Paul Ford joins us to share his perspective from all of those perspectives on the tidal wave of change from AI. We’ll talk about shifting expectations, shifting identities, holding onto the human in the face of rapid change, and a whole lot more.

From the pages of Wired and The New York Times to your ears, here’s our conversation with Paul Ford.

Peter: Paul, thanks for joining us.

Paul: Oh my goodness. Hello friends. It’s good to see you.

Peter: It’s good to see you. I’ve been following your work on the internet for probably 20, 25 years.

Paul: This is it’s just ridiculous at this point. Like it just… the three of us, anyway, it’s great to see everyone. I don’t even know if we’ve even met half the time. Peter, I think maybe you and I have been in a room a few times, but

Peter: yeah.

Paul: It’s lovely to see everyone just getting our career started, getting stuff moving.

Peter: Career. I think we’re getting our career restarted.

And maybe that’s a place to begin. It appears you’ve been going through it the past few years, and I’m curious how you introduce yourself, how you talk about what it is you’re up to now.

Paul: It’s changed from time to time, but essentially I am the president of a services company. It works like a services company. People come to us and they say, I want you to build my thing, just like the industry I’ve been in forever, except the nature of building a thing has changed really fundamentally.

You can spin up software very quickly and, I’m the president of Aboard. We are a AI, sort of, delivery org. We help you get your head wrapped around a lot of these changes. And we help you ship software very quickly. Sometimes with our custom tooling, sometimes just using Claude Code or whatever.

And so I come from that background. You’ve all been in and out of services, like I have throughout your career, and actually it’s, kind of relaxing for a minute because a lot of times I’m talking as someone who is also a former journalist and I have to be on and know everything.

In this case, you understand where I’m coming from. I don’t know what the hell’s going on. Like I used to charge a certain amount of money. I used to, I used to be like, Hey, I’m gonna do this and I’m gonna get a product manager. I’m gonna get a designer. Maybe a junior designer too, and a couple of engineers. One for back end and one for front end. And then I’m gonna give you a thing and it’s gonna break, and then we’re gonna figure out how it needs to work. And then about six months later, you’re gonna gimme a lot of money, like hundreds of thousands of dollars, and you will have your thing and it will be good.

And that was 20 years of my life. And that is not the case anymore. And I think you guys are probably dealing with this just in the exact same way. I’m curious what, where you’re at.

Peter: Before we answer that, I have one specific question. No. ’cause you had an agency, you had Postlight, Jesse and I also had an agency in ye olden times

Paul: What was it? No, you gotta, you gotta name it’s for the people.

Jesse: Name it for the people,

Peter: Oh, they know Adaptive Path.

Paul: There we go.

Peter: And the sense I got, and correct me if I’m wrong, ’cause I’m witnessing this from afar, you left Postlight, you started Aboard, which I got the sense was started as a product company, you had an idea for a thing, you were gonna build a piece of software to put into the world.

And that was my operating assumption until literally three days ago when I went to your website and I was like, wait a minute. They’re an agency. Why? What happened? And I’m curious what that story is, ’cause based on what you were just saying, I think it’s probably illustrative of something going on right now.

Paul: Yeah, no, fair enough. So I was the CEO with my co-founder, Rich Ziade, who was the president of Postlight, which was a product focused software development firm in New York City, very New York based. We did a lot of work for big banks. We did a lot of work for the MTA.

And so everything that you would expect about boutique and it scaled, it grew pretty quickly. And it got to about a hundred plus employees many in the US, a few globally. Especially in Beirut, which is where Rich is from. He’s from Lebanon.

And all those things selling all day long, so on and so forth. We, during the pandemic, stepped back, new leadership took over and it felt like time to move on.

The company was purchased by NTT Data Americas and became part of a big product group. And I was contractually obligated not to sell services because my power as a salesperson is so incredible.

Jesse: Yeah.

Paul: Just, Just, if you’re not careful, I will sell you a six month product engagement while you’re not even looking.

Peter: Alec Baldwin has nothing on you.

Paul: No, exactly. I’m just ready. I’m ready at all times. I love to close. A, B, C.

Jesse: A, B, C.

Paul: Exactly. But Richard and I really like working together and we didn’t go with the acquisition.

It was one of those where they were just like, cool, we’ll take it from here. And so what we sat down to do was to build, and it’s now been through many iterations, a kinda white label….

We were like, let’s take the advice everybody always gives you. Let’s build a version of what we used to do at the agency that we could license. So every project you sit down and you build Kanban and you do user authentication and integration with Microsoft a lot of just the basic data and scaffolding stuff.

And so we built that. That was version one.

And then we were thinking, there’s just a series of decisions that you make when you’re building something, some of which are good and some of which are bad. So we made a version that was a little more open to the world where people could manage data, but the theme has always been from day one that we would take this to organizations, and organizations would use it to accelerate software development.

And so that felt good. And we had leads and we had clients customers really, because you’re selling a product and they were using it internally and all those things were happening.

And then ChatGPT showed up and started writing code. And I was like, whoa, this is gonna change everything.

And we all kind of agreed. And so then the last couple years have been about iterating in reaction to the fact that the cost of software is going down. And the need for acceleration, even as a concept, is becoming commoditized because you can just deliver stuff all day long.

And so a lot of the things that I thought I was way in the future on, I’m not anymore. Nobody is.

Because what the hell is a Kanban board? Or like sales or a CRM if you can build a credible one in two hours?

And so we’ve been riding that wave and what’s happened is that you react to your inbound. And our inbound has been orgs saying, help us get organized around this. That’s great that you have some custom things that you’ve built that help us build. We love that. That’s really nice. Good for you. But we’re just trying to get this going here. Can you help us solve this? Can you help us integrate these three things? And by the way, could we also make sense of AI while we’re doing it?

So we’ve backed into kind of consulting plus custom tooling as opposed to custom tool with consulting around it.

Jesse: I think that one of the challenges that’s going on for enterprises right now is that they don’t know what they do know, and they don’t know what they don’t know.

Paul: There is a great Reddit thread now, where I think it’s in just like the Claude Reddit where an engineer is just like, CEOs keep giving us code in engineering, and I’m losing my mind.

right?

Jesse: terrible. It’s like the worst case scenario. And so it is this interesting sort of tension that teams find themselves in where the walls are collapsing. And the gap between thought and reality is shorter than ever.

Paul: Which we should be excited by, given our careers.

Jesse: We should be. Yeah. exactly.

And then I wonder about these teams, your clients, our clients, the people who are inside these organizations who are trying to get things done inside these much slower moving cultural environments,

Paul: I gotta tell you, I don’t know if you have this experience, but you’re dabblers, we’re all dabblers because we were early in this technology and that was what kind of got us into it.

And I just wrote a post about this for our newsletter. I feel like Patrick Swayze in Ghost: I’m telling everybody what’s happening. Like, You’re in trouble. There’s danger. And everybody’s like, wow, it’s cold in here.

I keep having that experience and what I realized is that what has happened is so weird. It’s so weird. And we’re used to weird things, but most of the world is organized….

i don’t know if you guys had this experience, I’m gonna be another web old timer, but like, there’s a lovely program. I taught it for a while and it was with people like Jeffrey Zeldman at the School of Visual Arts, the MFA in Interaction Design.

And there was a point where I went in, and it’s like me and Jeffrey and Karen McGrane and I’m like, oh, we’re the older weirdos here. We’re, like, the early ones because there were these just very put together graduate students who were like, I’m gonna learn interaction design, I’m gonna build a really good career.

And then they would go to FAANG companies like right away. They were good product people. And there’s that moment when you realize oh, this is becoming professionalized. That’s really good. That’s actually healthy. People are seeing this as a stable thing, as opposed to a wild wave to ride and figure out.

And I feel that that gulf has never been more profound in my life. Like, it’s very hard to see something so transformative. And then you take it to people and they’re like, yeah, but what about those Mets?

Like they’re just kind of like, they just would like, please, can we not discuss this anymore?

Peter: in my experience, it’s one of two things. Either, this is the only thing people want to discuss or this is the thing everyone’s trying to avoid. It’s hard to have just a casual conversation that might touch on it and then discuss other things.

Jesse: It’s got a gravity well, right.

Paul: Yes.

Peter: It is the gravity well. It reminds me Paul, I don’t know if you know Matt Jones, from the UK, one of the people behind BERG. I remember his frustration in 2004 or five, where all anyone wanted to talk about was the web. And he is like, there’s more to the world than the web.

And he was right. And I’m sure there’s more to the world than AI, but right now, like this is the actually intellectually interesting thing as well.

There’s something here that’s forcing us to reconsider stuff that we felt was maybe assumed. You outlined it.

And that’s been a theme that Jesse and I have been pursuing how for 20 years, from about 2000 to 2020, 2022, there was just this nice, steady kind of pace of growth and development and reliability.

Jesse: It felt like we were building a stable new thing

Paul: That’s right.

Jesse: For about 20 years, right. And then suddenly it wasn’t stable at all anymore.

Peter: Right and something’s happened. Even pre-AI with the layoffs and stuff in 23. But it’s definitely kind of timed to the AI moment.

You were talking about professionalism and you were talking about how we started as tinkerers. And I wrote on the whiteboard behind me the word humanities because the three of us went to school at around the same time, and all studied, I studied anthropology. Jesse was a journalist, and you studied English, the famous degree of futility.

But with our generic humanities backgrounds and not being afraid of technology, we were able strike out on these emergent technology of the web and the internet.

And now there’s a group of folks who… It got professionalized at places like SVA or bootcamps and other things in the last 15 or so years. And the thing I’m seeing, and I’m wondering what you’re witnessing, Paul, is that folks of our vintage are in some ways less rattled by what’s happening now because we came up in a discombobulated moment and in fact many of them are excited because it’s like, Hey, this feels like the late nineties again.

Whereas folks who arrived when it professionalized are the ones who are maybe the most off kilter because their assumptions are now shattered.

Paul: I think that there’s a few ways to hit at that.

I’ll take two angles. So angle one is, there was a great quote. They asked Linus Torvalds, who created Linux, who’s a little bit older than us, but not much. And they’re like, what do you think about AI? He is like, oh, it’s wild. All the vibe coding, it’s really interesting and it’s gonna really, it’s a real accelerator. Like he’s just vaguely into it as a technologist. He’s not shocked, he’s not an open source purist about it. He is just oh, there’s gonna be vibe coding. It is what it is.

But he is, like, but let’s be clear, nothing was as transformative as compilers, which was a really funny thing to say.

But then when you think about it, until compilers, you had to literally put in the code that the CPU runs in like hexadecimal numbers and, like, you were flipping switches and then one day you could issue a list of English-like instructions.

And that’s like at a thousand times cognitive speed up. Like, so many people, we just take it for granted. We take it for granted that you can have something that looks like Python or JavaScript and that will run, or even HTML and it will do something on the computer and you can learn that and you can teach it and so on.

And that, that actually wasn’t there for a really long time in the history of computing for all sorts of reasons. And so I really liked that framing because I was like this is another transformative thing. It is accelerated, it is different.

But we’ve been through major transformations before. That said, what’s different is it was not a, multi-trillion dollar, 30-million-person industry as it is today. And so the change is being felt really radically.

And so, we are very interdisciplinary by nature. It’s what attracted us to the medium because it was the first time that you could smosh the humanities degree with the technology, with the visual, with the written.

Like, It all started to congeal and you could kind of mess with all of it. And nobody could tell you no, you know, nobody could be like, you’re not allowed to do that. ‘Cause there’s the web, you can do whatever the hell you wanted. And so I think that is always very attractive to us.

But most people really want a little stability in their lives, like they really do. And we’re the freaks here, right? Like, we’re like, ah, well more chaos. Let me just huff it up.

Boy, that’s some good disaster. Get me more.

Peter: I dunno, I think I’ve reached a certain age where I’m fine with stability.

Paul: This is the thing…

Peter: Maybe when I was younger, chaos I could thrive on.

Paul: But think about actually, Adaptive Path is a good example. It was a transitional moment where you guys went, okay, wait a minute. We actually have to make this boring. And I don’t mean that in a bad way ’cause I’ve done it many, many times.

Like, I need to go to a bank like the one that eventually acquires you and I need to help them make sense of this because their world is interacting with this, but their systems can’t tolerate so much change.

And that’s you as little babies, you’re little babies going okay, we gotta figure this out because rhis change is so difficult for relatively nice people who I have meetings with. So we gotta actually systematize and structure this. We’re gonna make lots of diagrams with boxes in them, and it’s gonna be okay.

And we’re just not there yet with this stuff because every fricking week Claude is oh, by the way, it can make shoes now.

Jesse: You’re right. Yeah.

Paul: What would Adaptive Path be for the vibe coding era? Jesse?

Jesse: I, well, yeah. Okay. What would it, all right. Hang on. It’s such an interesting question because I think that a lot of what we did was about deliberately diving into unexplored territory. We were continually inventing methods and developing techniques around things that we had no idea what to do because no one had ever done them.

And so we had to improvise and adapt from a methodological perspective around the work, and what was actually to be delivered.

So we just recently celebrated the 25th anniversary of the company. And one of the things that I pointed out to folks is we did not even call this work design when we started doing it because we felt like we were after something bigger than what people thought design was.

And in this moment, in this time, people think they know what design is.

Paul: No, I mean, let me make an observation about what I think you actually sold. I think you sold empathy. You said you had a lot of skills, but I think you actually sold empathy for large systems. It was like we’re a big system and we don’t really know what to do next. And you were like, I have the skills that you need.

But more than that, ’cause that’s tactical, I actually have empathy for the fact that you’re doing the thing you’re doing and I would like to understand it. I’m curious about it, and I would like to bring my skills to it. And I think that was very comforting to people with the change, right?

And so when I think about the organization I’m building today. Everyone is a solution engineer. That’s like a mix of product manager, design, engineer, ’cause if you can ship anything, right? So let’s call everyone a solution engineer.

But our job is to be empathetic to people who are driving through this change who want to be able to access the system without destroying everything on day one. And I think that’s what you guys were too. I think it like that’s what everybody’s really hungry for as far as I can tell. They don’t wanna just build, they want to understand.

Peter: I’ve got two questions about your business. The first is, is there a type of client or type of project that is pretty typical that is coming to you and what are those?

Paul: So there’s what’s in-house and then there’s what’s inbound, right? And I can describe both in broad terms.

So in-house is like helping a big insurance company doing things to help them manage policies in new ways and analyze data.

So it’s a portfolio of, like, projects, like classic projects with a little bit of AI and a little bit of acceleration and a little bit of strategy and kind of putting that together.

The larger orgs are like that. They’re like, let’s just try to get this in. Let’s see what we can get. We like the advantages of it, but we’re gonna take it step by step. Security is very important. Auditing is very important.

The other in-house is, it’s a giant medical informatics play from a big not-for-profit. They want to aggregate lots of data around children’s health, and they need to do it in a HIPAA compliant way that’s very secure and safe. And then they want to be able to almost talk to the dashboards, right? Like they wanna be able to ask natural language questions about how services are being delivered across a large number of clinics. And so, that’s another one.

Those are kind of like almost classic big project engagements that are enabled and interesting because they’re AI. You know, there’s a team on them and so on.

What I’m finding more and more is that if there’s a theme, it’s that, wow, computers made a mess of everything, and if we don’t have to live with it anymore, that would be really awesome. Can the new computer clean up the old computer’s mess? And the answer is yes.

Like the huge pile of documents that was OCR’d can now be really rendered way more useful. The invoice system can be better.

The number one question that everyone asks on Earth, as far as I can tell, including babies, is what would it take to get me off of Salesforce?

That is like the absolute, like, literally people who are dying, their last words are, I wish I could have gotten off of Salesforce.

That’s, please don’t let me go…

Peter: They don’t want to have spent more time with their family. It was just off Salesforce.

just get me off Salesforce.

Paul: Why couldn’t we ever get off Salesforce?

I hear a lot from people who either tried to build up from SaaS products into a kind of a working system and then just find endless friction every day. I hear a lot from people with legacy systems who would just like to move a little bit faster. And then I hear a lot from people who are just like, I gotta get this into the org, but I don’t know how. And so those are the shapes.

And then at the same time, a lot of the things I’m seeing and living, delivering the services are really confusing because the design phase is different and the engineering phase is different.

Paul: And sometimes, and I have had experiences, a lot of times I’m building the product during the pitch, right? Because it’s just so fast.

And so then do I show that to them? When do I show them the value that they can have access to? Not because I want to get them… but literally ’cause it’s so overwhelming.

I don’t know if you’ve had this, but you create these artifacts and people don’t write back for two weeks because

Jesse: it’s

Paul: so hard to metabolize like what they just saw.

Jesse: This gets back to a very old tension between Peter and myself in our consulting practice, where I was always reaching for the farthest frontier that the client could possibly see, and then complaining that they didn’t sign on to my ideas.

And Peter’s like, well just, you know, don’t give them the 10 mile view. Give them the one mile view and get ’em to sign on to that.

Peter: Yeah. Give them the thing they can actually do.

Paul: No. We’re gonna just, I just want to pick at this scab. This is exciting.

I think, look, I’m with both of you, right? I like to see where the future’s going. And actually if there’s anything, my dynamic with my co-founder, I’m probably more the Jesse and my co-founder is more the Peter in this, but it’s always that collaboration, right?

Because I’m the guy who’s wow, whoa. I literally, I hit Claude Code in November when it got really good and I walked in the next day and I just turned to Rich and I went, death is coming.

That, those were my words. And he is like, slow down. The insurance industry doesn’t move that fast. And actually the insurance industry, if death is coming, they’re like, cool. We priced that in. It’s all great.

Jesse: Yeah.

Paul: So no, I think, it’s very tricky. Organizations cannot metabolize change.

I will say, I think there is a thing coming for all of us that no one has fully factored in yet, which is the security profile of the entire industry has to change because it’s much easier to hack systems than it used to be.

So I think if you were to really think about the right way to walk this into an org and just be like, let’s do some automated auditing and figure out where some of this stuff could be like made a little more firm and stable using AI, like let’s clean up some mess. Let’s think about security. Let’s audit your open source. Let’s make a good auditing trail.

Like, there’s a lot of system stuff that’s gonna have to happen because you can hack all day now at a nation-state level for $200 a month.

And so those changes are coming and they have really high costs. And I think probably we do have to react to them as an industry way faster than we were even expecting.

Or not. Or not maybe, hey, things work out. Security is one of those things.

Jesse: be fine.

Jesse: You touched earlier on the blurring of lines as you’re defining this role of solution engineer for yourself within your organization, and for a lot of the folks that we hear from who listen to this podcast, they are in-house design leaders.

They have got teams of 20, 50, a hundred, 500 people who are dedicated to design, whatever that means, as a value prop inside their organizations.

And now they’re looking at engineers doing what they used to call design and product managers doing what they used to call design. And their designers are looking for purchase within this landscape. They’re looking for a place where they can get some really meaningful traction. And so it comes back around to this question of what even is the value proposition of design as a function anymore in this blurrier environment? What do these leaders and these teams have to look forward to in terms of what they bring to the table and what they can potentially offer?

Paul: I think this one is thorny and it’s not thorny in a like, oh my God, time to start that bakery kind of way. I think it’s more complicated than that.

Let’s take this step by step. I’ve been doing a lot of thinking about this, I think there’s a few realities. One is an average human being in a technical context, an engineer or product manager can do far, many more design tasks without asking a designer than they used to be able to.

And I think one of the ways we get in really big trouble is we go, well, that’s not really design. But if it has a function for the audience and the audience doesn’t really feel that they’re being duped, then you’re at a loss now.

It might be disrespectful of the discipline, it might be not at a level of quality that you would ever put out for yourself, but the reality is you are at a loss because the audience has gone, oh, cool, that’s there. And it’s there in 10 minutes. So that’s, I like that. It feels good. It looks like an app to me.

And then there’s the secondary thing, which is that some of the models are good at certain kinds of design. I’ve absolutely had moments where I was like, that would’ve been a junior designer. I’ve never seen anything that come out where I’m like, that’s a senior designer level artifact. But, absolutely things that are, like, wireframe-plus or relatively light, type heavy, here’s how the onboarding would work, right? I, I’ve seen good product.

So I think you have to get close to that and you have to know it, and I think you have to know how to steer it and understand it so that you’re delivering it with the information that you have in your discipline as opposed to getting frustrated with other people for doing it.

You have to enable them. Now if you’re in a hostile environment, there’s a lot of bad blood in our industry, right? There’s a lot of like, oh, design always takes forever. And then like product is snooty, but also can’t do anything. And engineer….

And the reality is everybody thinks they can do everybody else’s job. And then it always blows up. And this has been going on way before AI, so product is so excited that they don’t need engineers, ’cause engineers are exhausting.

But I keep seeing product managers ship the same fricking thing that just looks like a spackled together database that they’re like, I’m vibe coding, aren’t I amazing?

And I’m like, yeah, but honestly that’s like, you could have done that in Airtable. Like, I get it, I get that. It’s cool, but it’s not really a product even though you’re the product manager. Like you forgot that part. Everybody keeps forgetting their actual thing, right?

But I gotta say our design team, we’re relaunching our marketing website because of course the company changes. And we were trying to use… Figma has this product that lets you actually publish straight to the web. Now I would not recommend that but we’re doing a lot of Claude Code based automatic translation, like out of Figma straight to the site.

It is good, it’s a little too much tailwind for my liking. Like it’s a little too garbled, but it’s good, it’s credible, it’s a first pass. We’re gonna need to turn it into a proper CMS template and that’s gonna require human intervention and engineering.

But those are designers. And at one point I said to one of our designers who’s like, look, I really wanna learn this stuff. I was like, okay, I’m only gonna talk to you for 10 minutes. I won’t give you any more advice. You have to go do this and then report back. Go create a component system to solve, I might have said video or like some sort of problem related to one of our clients. And I was like, make a component system and then I want you to ship it as a React storybook, complete, and figure out a way to host it.

And two hours later he came back. He’s like, wow, I, that’s okay. I can do that. It wasn’t the greatest React storybook, it was missing, there weren’t a lot of animations. There weren’t a lot of variations, but it was pretty good product, right? It was okay.

And so designers are not out in the cold, except in that way that designers always put themselves in the cold.

You’re like, I’m a small bean, and I cannot think technical thoughts, only art thoughts. And like we all have to get over that.

Peter: So I wanna unpack a little bit of what you were just saying.

You mentioned earlier how everybody in your organization’s a solution engineer, but when you were just telling that story, you were referring to designers. So you still have a mental model of people maybe in the roles that they had been in.

Paul: Oh yeah. Let’s not, yes, I’m the president of the company, but I’m also a solution engineer who uses the tools that we’ve created that are sitting in our GitHub repository and lots of Claude Code in order to prototype.

However, I really don’t push things to production in the org. I’m mostly here to explain where I think things are going work with my partner, et cetera.

Our engineers are absolutely able to think in architectural ways that our designers probably won’t, and our designers are able to think in terms of visual systems. What I’m finding, and I think we’ll see it, the novelty of it is so wild, right? Where it’s like, Hey, use giant component system X.

If you tell it, if you say, Claude, man, I just want you to use IBM Carbon, good system, go to town. It will make you something that looks very component-y and good and solid, and then it all starts to look the same. I don’t know, is design in the future just skinning component systems? I don’t know.

An enormous amount of our work still ends up going through classic design processes. But if a designer can solve a problem by typing words into a box, they should be able to do that. They shouldn’t necessarily have to wait. It should be auditable, somebody, a product manager.

So there’s different kinds of ownership, right? Like a designer should be able to do stuff if we’re really just changing a component and I can see a future state where that could ship to production without a lot of other people involved. We’d be willing to take that risk.

Someone whose background is design probably shouldn’t establish an authentication system, and push that to production.

But they could say, it’d be cool if login worked like this. And I actually prefer email based login. That’s better for this than trying to do OAuth. And somebody might be like, yeah, that makes sense. And then everybody types like three sentences into the box. Somebody goes, Hey, it looks pretty good.

Jesse: Yeah.

Peter: It’s a canard now around roles blurring. And, your adoption of solution engineers struck me as a recognition that whatever we might have been once, we’re all doing something similar.

Paul: Now that we have returned to our services roots, what is a solution engineer? It’s somebody you can talk to who has an understanding of technology and platform who can help you figure out. What the next step is, and often that is before a contract is signed. And so a big part of this is just when an organization comes in or a person comes in and they want some help, you’re like, all right, talk to a solution engineer.

A solution engineer might be coming out of design, product management, engineering, front and backend might be an organizational leader or just a pure manager, but they’re able to do something. They can make you an artifact that looks and feels like code, and so I think that it’s working backwards from that change as opposed to like this very prescriptive role.

It’s just like when someone walks in, I want to introduce ’em to someone who can solve their problem. Hence that title.

Peter: And this touches on something I’ve been thinking about. So I do a lot of thinking on organization design, and I’m wondering how you think about shaping teams as roles blur. What is your organizing principle to say this collection of people, anywhere from two to five or however many, are the right collection of people to solve this client problem that’s coming in? Like how does that calculus operate?

Paul: It’s still pretty classic, right? First of all, I don’t believe, in general, people should not go alone in any client engagement. It’s dangerous.

Jesse: It is dangerous to go alone.

Paul: it is, yes, exactly. Take this and I hand you, Claude Code.

Like I don’t like to sell alone. I don’t like alone in a services org because you should always have a couple people thinking thoughts. But when I think of currently org structure, what I’m finding is that product manager as solution engineer kind of depends on the profile.

If they’re more technical, they can really get through to the very advanced demo, they have access to, like a good platform, they know how to get things into production. They can do an awful lot.

Paul: It’s really almost, and I feel sad about this. I’m not really ready to commit to it, but I feel that the roles become more about validation than about production, right? So it’s like a product manager validates that this is a real product. It’s not just like pixels slapped on top of a database, but that it really actually understands the flow of the business or the organization and their needs.

A designer thinks about experience and they think about components and they think, honestly, a lot of times designers are thinking about scalability of a design experience. They are willing to use all the tools necessary to make sure that people can have consistent, reliable experiences when they come and sit down. That is a validation pass, if you are not the one who is moving the pixels around.

Now they might mock something up in Figma, but then a robot might build that rather than sending it to an engineer. But an engineer should review that robot’s output to make sure that it is valid, good, stable output. And I’m not imagining a world actually where all we do is say the robot did a good job. Because I think there’s lots of stuff that needs to come from people, and I think there’s a lot of stuff we need to do.

But that said. I’ll give you an example. I have an automatically generated newsletter every day, but I built a lot of tooling around it. It reads five or 600 sources. It keeps sources connected to summaries and so on. I never share the output of it. It’s just there for me and a couple people, and it’s my AI coordination newsletter, and I use it to know what to post on LinkedIn and so on.

I have to go read the articles, I have to do lots of stuff. It extracts numbers, so on and so forth. I am the validation before any of that content can reach an audience on LinkedIn or in a newsletter. It has to be there because otherwise it’s really meaningless. The Pure newsletter experience, I think is interesting, but unless somebody’s using it that way, it’s not that great of a product.

It’s a very good product to feed what I’m doing, but it’s not a good product unto itself.

Jesse: So it’s interesting to think about what all of this means for the leaders of design teams inside organizations as they are trying to reshape, resculpt their teams and honestly their value propositions, right?

Paul: What are you guys hearing? Like you know, more designers than I do.

Jesse: Yeah. So in the conversations I’m having with design leaders all the time, they’re terrified.

Paul: Yeah, that’s fair.

Jesse: The thing about it is that what the machine is best at is mediocrity. Which is the thing that designers have been fighting against this entire time, right? Like designers really see themselves as holding the levees against the incoming flood of mediocrity that executives are so desperate to unleash upon customers.

And then as you point out, then the question becomes what are you bringing to the process anymore? It’s not execution against base level design standards, best practices, value propositions. It’s gotta be an elevation. Right?

Paul: Yeah, it’s not like you’re like, Hey, here’s the branding guide. Like the fantasy now is I gave you the branding guide and the robot will do all the design for you based on the branding guide. It is, it’s very scary.

Let me describe a future state, but I, here’s what I’m gonna describe a future state, but I don’t really have a way to get us to the future state.

So right now you have these big

Peter: So you’re an underpants gnome.

Paul: Yeah, exactly right. No I, the problem is I think that the bullet point two or three, I can’t remember what the underpants …

Peter: Steal underpants. Two, question mark. Three: profit.

Paul: Yeah, bullet point two I think might be like a lot of chaos in reorganization.

We have a podcast at work. You can find it on our website, aboard.com. I just interviewed a really wonderful writer and thinker. His name is Andrew Leland, and he has a degenerative eye condition, so he is losing more vision every year. And so he’s become, even though he used to edit the Believer, he is become a really good…

Peter: Oh, I’ve read his work about that. Okay.

Paul: He’s wonderful. He’s wonderful and the reason I wanted to talk to him is he’s become a big sort of nerd, right? Because he is in text editing and using Claude Code and he started to talk about how blind users and low vision users are hacking their own tools and building their own systems.

You know, like Wikipedia is very accessible, but it’s not always really scannable to someone who doesn’t have vision. And so people are making ways to read and find Wikipedia for themselves, right?

So I want you to think about a future in which those needs, which could be the needs of a disabled person or the needs of a corporate leader, it’s like they have really specific things that it could actually help them do their jobs. But literally somebody who’s good with this stuff could sit with somebody who realizes, who’s starting to lose their vision, but has other particular needs or websites they really must visit for their job or things like that, and build a solution just for them.

And a designer would be incredibly useful there. They would be thinking about things that aren’t visual actually. And at the same time, I don’t wanna be too utopian here. You need to fix the real problems first.

But what really stuck with me is that, if you think about a future where everything is commoditizable and moves fast, and people can have very customized stuff, then individual needs can be addressed in ways that they couldn’t before and maybe they’ll scale out to other people.

But how do you get there from a 400 person team inside of like a giant electrical utility company? I don’t know if there’s an organic step-by-step path where everybody gets to keep doing what they’re doing.

Jesse: It’s interesting to see where the personal meets the professional within this, because the web, as you pointed out, kind of made its way in enterprises because people inside realize the value of these tools and they advocated for them and they set up web servers under their desks and all of that stuff.

And in this age that you describe, which I imagine as an age of infinitely disposable software, that you can create something incredibly complex, incredibly bespoke, that would’ve cost you $500,000 for a team to build for you, that is just for you to plan your vacation and you’re gonna use it for just that purpose, and then you’re never gonna look at it again.

But the cost of it is almost nothing to actually create. So with that in mind, then, what you see inside enterprises is every team has its own tooling. Every lead designer has their own way of orchestrating and architecting the solutions that enable them to deliver what they deliver.

Paul: Yeah. So now we have to build unified systems for bringing all of those systems together. And then everybody’s gonna hate the unified system and go and vibe code their own solutions. Except it’ll be for Claude Opus 35. And it’ll do it just ’cause they whistle at it.

And that’ll generate a whole lot of data and be insecure, like the cycles of disaster that define our ridiculous industry are also getting accelerated.

I can tell you from history, right? Like I’m in New York, I’m very publishing adjacent. I worked on a lot of big content platforms and so what happens is everybody has one unified content platform for the entire magazine conglomerate, right?

And everybody hates it. And then they fire the CTO and the new CTO comes in and is it’s cool, you can use WordPress. And then five years goes by and they fire that CTO and the new one comes in and goes, how the hell can everybody be running their own WordPress? This is a disaster. We’re gonna bring everything, we’re gonna build our own custom CMS, we’re gonna bring everybody into it.

And it is a beautiful cycle. It’s like a, it’s like a, it’s almost mythic, right? And I think you’ll just get that, except it’ll be like literally on a four-month interval, which will be tough for the CTOs ’cause it’s hard to source that many.

But here we are.

Peter: Jesse mentioned design leaders being terrified. I think I’m seeing a broader swath in the conversations I’m having.

I have one design leader, I mentioned this person in one of my newsletters, who’s actually primarily frustrated because he is so far ahead of the rest of his own organization that he doesn’t know how to bring them along with using this tooling.

Paul: It is the ghost problem. He can’t, yeah, I get it.

Peter: Well, yeah. he’s seeing opportunities for this tooling to improve how the business operates, and he can’t get anyone else to care about it. They just are like, no, I’m just gonna keep doing what I’ve always been doing. So there’s frustration.

I’m seeing empowerment from some leaders. Jesse, you and I have been talking about Z from CloudFlare, and she’s an atypical design leader, but she’s a design operations leader at CloudFlare, and she’s been writing on her Substack, and I’ve had some conversations with her about it, about how she’s gotten the 30 some designers at CloudFlare outta Figma and just into an LLM that has the design system, and they’re just like making live prototypes that they hand over to engineering to be wired in and shipped.

And she’s like, this is awesome. We’re designing faster, better, closer. There’s fewer levels, fewer stages of interpretation where things can go wrong.

You hear this from some other design leaders where now they can have their own repos and clean up three years of design debt that was never gonna be prioritized by engineering. Engineering’s like, please have at it. Stop bugging us. We are more than happy to let you just solve those problems.

Paul: Yeah, right now, but like a year from now, they’ll be like hold on a minute. Wait a minute. I’ll take it. I’ll take it. It’s okay.

Peter: Well maybe.

And then, I just had an email from a head of design at a large bank, and he was somewhere in the middle, which is just like uncertainty. What do, he was asking me, what are you seeing? We don’t know what’s going on.

And so it wasn’t fear so much as just ah…? And then yes, there are the anxious and fearful folks.

And so I’m seeing a spectrum and I keep drawing normal curves because the normal curve is helping me categorize what I’m seeing, which is that, the farther you are along on your AI maturity, right? There’s folks who are here and they’re on the more confident end of the spectrum and they’re doing fine.

And then there’s people in the middle who are like, I don’t know what, and then there’s people on the kind of the other side. We just had Jorge Arango on, and he had this line: don’t think that this is a nothing burger. This is a burger, right?

He, we might not know what kind of burger it is, but it’s a burger.

But there’s folks back here are the, either the nothing burger, or, to overextend the metaphor, they’re looking at the menu and they’re just like, all the burgers are like about to fall upon them. They just can’t make sense of the variety of burgers that are out there.

And so there’s this spectrum and I don’t quite know what to make of it. Except that it feels like the folks who are feeling best are those who aren’t afraid. They’re approaching it with curiosity as opposed to anxiety.

Paul: I will tell you how I approach this.

So first of all, I think that, as a technology landing, this is the worst rollout in history, right? It never made sense. It shows up out of nowhere. The leaders of the companies are, they have many qualities, but they’re not great communicators about what’s coming. They don’t know the capabilities of their own platforms.

And it comes on a level of hype that is essentially trying to match Bitcoin hype, but with a weird database that talks to you.

Like, a lot of folk narratives have emerged, you know, it uses more water than anything. And then people come out and they’re like no, it doesn’t use that much water. But I’m like, let ’em have it. Let ’em just have the fear. Let ’em have the sense that it is ecologically bad. Let ’em have it. Don’t fight everybody tooth and nail on the fact that some of these things are very destructive and they’re very confusing and they’re not good for society and they’re messing stuff up.

So that’s a, just go in with empathy and know, and I felt this, I’ve been writing about it in public and my God, you take some heat when you say, I think this is real, because people are very committed to a narrative of the nothingburger.

Peter: Well, in particular, people with background similar to ours, but who are not as technical, who stayed in humanities practices and who have seen more directly, I think their livelihood threatened by these tools. And so they’ve just been like, they’ve noped all the way out.

Paul: That’s right. I gotta tell you though, I just had a class come in, it was a journalism class from the New School. It’s a very progressive school in New York City, and they came in, and I actually thought they were gonna be grad students.

They’re all undergrad and they were, they’re babies. They’re just lit–, they’re so young and they’re just full of ideas. And I didn’t have to say much. They just asked questions.

And at one point I was like, look, what do you guys do with this stuff? And almost universally, I would say, they’re all, yeah, average age is like 19, 20. And they were like, oh, I don’t use it. I’m in college for my brain. And it was just this very weird moment where you realize this has been there since high school for them. It’s very normal.

Some of them said they use it for work. One person was a vibe coder and so they were using it those ways, but their relationship to it, and I think what happens is, everything gets to such a fever pitch so quickly that we forget that humans are higher primates capable of reasoning and organizing their lives, even with new technologies.

And I’m looking at them and I’m like, ’cause you go online and it’s just like, it’s either people saying like, everyone who even thinks the letters AI should be shot and thrown in a river. And then other people who are like, the Lord came to me last night in the form of a prompt.

And you’re just sort of like, you’re caught between it and you just get this assumption, especially ’cause the news is so bad and like…

Peter: Yeah, this couldn’t have happened at a worse time, at least in the United States from a geopolitical standpoint.

Paul: And also from a climate change point of view, like the timing’s terrible and everyone who is in the news running the shop is an absolute reprobate right now.

And so you assume that that is the world. Most humans really just want to have a nice dinner with their friends on Friday and actually don’t want to talk to the robot all day.

And, but then the thing is also we are talking to the robot all day, I think we get very skewed. I think a lot of people don’t take this anywhere near as seriously as we do.

Now that said, you go back to that design team of 500 people. Is this existential? It could be, and we have to be honest about that.

I don’t know, but when I talk about a future state where everybody can get their thing, and that’s very utopian and positive, but if we talk about what would happen to go from step to step, it’s a lot of pain.

So I think there’s probably balance in here. I don’t think we get to this moment where we’re like, ah, that was fun, but it’s over now. Let’s get back. Let’s open up Aldus Freehand,

Jesse: Right.

Paul: and get back to work.

Jesse: I think that touches on an interesting thing in here. You and I both come out of a writing tradition, a journalistic tradition. And for me that writerly approach has always been a part of the way that I’ve approached design in terms of thinking of it, in terms of storytelling and so forth.

But what I’ve found in decades now working with other designers, is that most of them don’t think that way. Most of them are, they’re much more nonlinear, they’re much more visual, they’re much more abstract, honestly, in the way that they think about things. And they are now being asked to turn their ideas into words in a way that they haven’t had to before.

And I find myself wondering what that means for the skillset. So let’s leave aside the blurring of the roles between design, product and engineering, but just simply the skillset of describing what you intend to create in language. And what does that mean for the shape of teams, the way that people’s value is even judged, you know?

Paul: There’s a couple different ways to look at it though. This is a very assistive technology in this way. I have a friend who, he is a developer and he is, he’s a black guy.

He works for Microsoft. And he’s like, oh man, this really helps me. I actually can make my prose sound a lot more white with these tools. It’s really useful for me when I’m like, doing a brief. And I was like, oh yeah, that actually the logic of it was impeccable.

He’s a very good, very clear writer. He writes a newsletter. But I got it. He was just like, this is, it’s a safety net for him, right? He was just like, I’m in this corporate environment. It’s a way for me to be in charge. And I really respected that. I respected that use of it and it is often in my head.

And so I think we’re just kinda, everybody is, am I gonna be marooned because no one will help me? Am I going to have to figure all of this out myself?

And I think the way these technologies have landed, like I was just saying, right? Like they, came down from nowhere with no instruction manual and the sort of eager beaver types like us are like, okay, I know what to do.

There’s no big O’Reilly manual yet. I’m in paradise. But now build a system for them, right?

It’s really cheap to build a system now. So if we want to help designers, what are designers good at? They’re good at thinking in terms of visual or, but also just systems. Systems and ways that data interacts and usability and how to represent data and ideas in ways that are tractable and sometimes touchable.

And so what tooling could we be building for them? Given that everyone can build a lot more tooling than they used to be able to, to help them express themselves. Could we give them a nice interface with some guidance so that they could do more of this? Because the cost of that is really low.

And so there’s this assumption that’s driving me a little bit bananas. It’s not you, it’s me too. Like everybody’s caught in this, which is just, no, it didn’t pass the test.

So you’re going to the island and then you’re gonna have to fight for beans, right? It’s just everybody is, oh my God, yeah. I just need a can opener so I can survive. And it’s just yeah. You may not be in Figma all day, which I mean, God, I don’t even know what Figma is anymore. Have you looked at that thing lately? It’s like an operating system. It has a CMS built in. I don’t know.

But, we could be building tools for designers to explore and figure out where their talents are gonna go inside of these orgs. And I bet you’d see value in a week, ’cause it’s so fast to build the tools, but we’re not there yet.

Like I say that in a very abstract way. I’d love to work on that. I think it’s a really interesting puzzle, but it’s like nobody’s quite buying that yet. Like nobody at the big bank wants to build a custom design exploration LLM tool in order to maybe help designers contextualize themselves in the world of AI that’s like $200,000. They would really not want to spend, they’d rather buy a product or hire a vendor, right?

Unless you’re just going to do the Oracle thing and fire 20,000 people, which I don’t think is the right move at this time. You might want to think about that. You could build frameworks here and we can get ’em done real fast.

Throw ’em away if we don’t like ’em.

Peter: So, a separate thread that Jesse and I have been pursuing on our podcast is something we call Liminal, and it’s addressing… what we were talking about is now is this liminal moment, between a way the world worked that we all understood, and a new way the world is about to work that is very fuzzy and unclear, and that we’re caught in this.

And, something that I’m witnessing in your life, career, whatever, is that you’re navigating liminality quite actively, and I’m wondering what you found that helps you through that. Like how are you staying somewhat true and upright when you’re probably being buffeted by these winds of change constantly.

What’s worked for you?

Paul: Well, I mean, I think it’s very real, right? The way I describe Anthropic and OpenAI is, I’m looking right now in our office, we have a view and I can see the Hudson River, and I’m like, it’s just like two aircraft carriers just came up the Hudson one day, and it’s like, what am I gonna do?

I can’t, what am I gonna yell at them? It is a very different industry than it was a year ago. So I think acknowledge that you are in a liminal state, acknowledge the frustration and the change, but I think you also just have to acknowledge that this new power exists and you don’t control it.

Social media gives you an illusion of control. You can yell really loud. So that was the last, big web revolution with social media. And it let you feel that you had a voice and it made you feel that if you didn’t use that voice in a very specific way, you would be betraying something, right?

So we’ve been going on like 10, 15 years of, you gotta do something, you gotta be in there, and now this thing has happened and it keeps happening, and you’re not gonna put it back in the box. You can’t yell it away. It won’t behave, it won’t do what you want.

And I think just accepting that, and, you say that and people are like no, it won’t. And I’m like, okay then it’s down to like government regulation, terrorism. What are you gonna do? And they’re like it just has to stop. And I’m like, I can’t do that for you.

And so just like accepting that we’re in this moment where we’re a little bit powerless because the next reaction people have is no, you’re not, you need to do something. And it’s no, I am powerless to go back to the way that the technology industry used to be. I cannot go back. It won’t work.

So that’s A.

So then B is, what are your limits here, right? My limit is, it never is gonna write a word for me. I don’t want it to. If AI’s gonna write a word, it can say at the top, this was written by AI, but it’s never gonna be me, so I’m not gonna let it. That’s just, sort of like, the writing.

But the coding, I don’t feel as strongly about the code. And so figuring out what the parameters are and so on. And then acknowledging that this is equivalent to sitting down to a Thanksgiving dinner mentally, where you sit down to dinner and it turns out that you’re actually having Thanksgiving every day, which is a lot.

It’s nice once or twice, but then you’re like, I’m good. And then the turkey is made out of nougat, like, it’s so much coming into your brain. You just, you’re like, ah, oh, you know, you thought you just want a sandwich sometimes and you can’t even get it because Claude, Anthropic just released 25 new products in the last 40 minutes.

And it just keeps accelerating. It keeps accelerating. Everybody’s in it and everybody feels like they’re on an island.

And the design team feels abandoned because everybody’s so excited. And the CEO is vibe coding and the engineering team is like, what the hell am I gonna do with all this mess? I don’t know.

It’s like the classic thing. You gotta talk to your neighbor, you literally, you have to go and talk. Nobody will do it. Nobody will be like, Hey, how you doing? Nice to see you. That’s too much for us right now. Cognitively, we just can’t and can’t handle it. But that’s it.

So I, I talk to everybody about it. We host events. When people hate it, I listen. And I’m trying to make this a part of my social reality as opposed to just this thing that’s being thrust upon me. And that helps me.

Mostly I love it. You know, Simon Willison, the developer, he’s as far into this as you can go.

They talk about the idea of Deep Blue, which is a funny pun if you’re a big nerd, but like the idea that, you get this sort of sense of sadness watching your career get devalued.

And I think that’s fair. You should acknowledge it.

But also and this is the last bit I’ll say on this, but like what the hell was our goal? Our goal was to give this to everybody.

This is why the web was cool. Everybody could publish, everybody gets to participate. And it is weird and upsetting that we built this enormous multi-trillion dollar mega thing that has made a lot of people able to have private jets and gotten a lot of other people good jobs in houses.

That part, a lot of that’s really good. But the flip side is that everybody’s gonna get to make a thing. It’s like back to Xerox PARC ideas from the seventies and in all the anxiety, we keep slipping away from that. I want to give everybody all the software they ever could want and see what happens.

I think that’s amazing.

Jesse: Fantastic. Paul Ford, thank you so much for being with us.

Paul: Anytime my friends.

Jesse: If people wanna catch up with you on the internet, how can they do that?

Paul: Oh God. The worst thing is, it’s just LinkedIn these days. But go to Aboard.com our website. You can easily find me [email protected]. Paul dot [email protected]. I’m on Bluesky, but not as much as I used to be. Anyway, let’s not even do that right now. Let’s, anyway, I’d love to hear from everybody. Everybody love it. I love it. All the thoughts.

Peter: All the thoughts to Paul. Thank you so much.

Paul: Blessings, my friends. Thank you.

Jesse: For more Finding Our Way, visit findingourway.design for past episodes and transcripts, or follow the show on LinkedIn. Visit petermerholz.com to find Peter’s newsletter, The Merholz Agenda, as well as Design Org Dimensions featuring his latest thinking and the actual tools he uses with clients.

If you’re looking for help with AI transformation or you just need a private advisor to help you solve your hardest leadership problems, visit my website at jessejamesgarrett.com to book your free one hour consultation.

If you’ve found value in something you’ve heard today, we hope you’ll pass this episode along to someone else who can use it. Thanks for everything you do for others, and thanks so much for listening.

For more about The Future Of… Design conference: https://www.thefutureof-conference.com/.
Use code FINDINGOURWAY for 26% off the registration price.
Find out more about Jesse James Garrett and his upcoming live session on AI Transformation at https://jessejamesgarrett.com/
Find out more about Peter Merholz at https://petermerholz.com/

Jesse: I’m Jesse James Garrett,

Peter: and I’m Peter Merholz.

Jesse: And we’re finding our way,

Peter: navigating the opportunities

Jesse: and challenges

Peter: of design and design leadership.

Jesse: On today’s show, it’s our first ever live broadcast on YouTube. Recorded April 3rd, 2026, design consultant and industry analyst John Gleason returns to the show to explore the ideas behind his forthcoming design leadership event: Are you ready to lead? We’ll talk about the role of boldness and vulnerability in design leadership, how leaders can position their teams for greater strategic impact, and how to advocate for a larger value proposition for design. Now here’s our unedited live conversation with John Gleason.

Peter: Hi everybody. Welcome to an experiment in, for us, at least in podcasting, not that others don’t do this already, and, that’s what we’re doing right now.

Jesse: We are finding our way in more

Peter: We are finding our way with live streaming and get, kick us off here. Just a quick, introductions. Most of you will know Jesse and myself as the hosts of your podcast, finding Our Way, and we have with us our returning guest, John Gleason.

John is a, I think of you as a, you can change this, if you choose, but I think of you as a design and business consultant. You have a background, primarily in business, but you were at Proctor and Gamble during their design revolution. And we got to know you because about a year ago this time, you hosted an event called, the Future of Design, where you posed the provocative question is design dead?

Jesse and I didn’t attend that event, but we heard the things that came out of it, were intrigued, and we had you on our podcast last June to talk about it further.

And we know that you are planning a new forthcoming event, for the future of design in, mid-May, but now you’ve got this subject, are you ready to lead?

And so we thought this would be a good opportunity to dig into what’s going on with design leadership, what you are seeing with your background in packaging and brand design and industrial design, what we’re seeing in the worlds of UX and digital product design, and see where this conversation takes us.

We are live. I will be checking the chats because, you know, at some point we would love to engage some audience involvement. John, anything else you want to say, before we dive into the conversational part of our discussion?

John: Part of the context that I wanna offer I’ve known about the two of you for a long time and then became a long time listener, first time caller when you invited me to join the podcast last June.

Peter, if recall, part of it started with, oh, I’m glad those things don’t happen in our world. This idea that design’s dead and declining, a decoration station, and then you and I talked and chatted and we both had some revelations and realizations that maybe there’s more commonality across the types of design activity, than differences, because the activity is different or the outcome or the artifact or the thing being created.

So I’m delighted to be here in part, to open up some dialogue for me to have a chance to continue to learn, but also expand the dialogue and the discussion around the ability for design to influence growth and culture and other things.

Jesse: So John, I’m curious about this year’s event and the direction that you see the conversation heading.

Here in the tech space, it continues to feel like a lot of bleakness, a lot of uncertainty, a lot of doubt about what the future holds. And I guess I’m curious about where you see the conversation headed that helps to resolve that.

John: I think one of the, I guess it’s an aspiration that we had last year when we, the three founding partners for the future of conference, decided to do the silly, crazy, stupid thing of, let’s produce something that gets people together, was born out of observations that I’ve made as I’ve had a chance to peek inside 150 or so big companies in the last 15, 20 years.

And that is… most design and business leaders, and this is true of marketing or supply chain or finance, they’re in their world, inside their company solving problems and managing challenges. But because they don’t often get a chance to get out and meet with their peers they think that those problems are unique to their own circumstance. And then because they think it’s unique, they think it’s confidential and sensitive, so they can’t talk about it. And then because they can’t talk about it, they have to go try to solve it themselves without help, without guidance, without a roadmap. So part of the original ambition was, let’s create a forum that gets people together first to build awareness that their problems are probably not as unique as they think they are.

And then use the power of the community to help solve for some of those things collectively, to accelerate the ability to change the trajectory or direction or arc of where and how design contributes to business impact, to career development, to cultural dynamics.

So that is a foundation. One of the things that came up during the conference last year many times, which led to the theme that we have this year of, are you ready to lead, is there’s all kinds of training in schools and university degrees and the like for the craft of the businesses that any of us are in.

Jesse: Right.

John: But there’s generally nothing that teaches those people how to navigate complex organizations, how to influence people with more power and more stripes and more influence than themselves.

How to set a vision for something and get alignment for that vision. And so part of that is let’s use the forum that we started to create with the future of and begin to use, step two or round two of this as the opportunity of people sharing what they’ve learned on their journeys. The hard knocks. The things that that maybe they did really accidentally or on purpose. Again, as a way of trying to accelerate the ability for people to use some of those tools and frameworks and roadmaps and checklists and principle what, whatever that people are willing to lead with as a way of trying to arm the industry more broadly as a way of trying to elevate design more strategically and more profoundly.

Peter: It’s interesting you say that. I’ve been having a similar thought where… So as Jesse suggested, in, in the field that we’re primarily in, this UX and digital product design, there’s a fair bit of consternation and uproar. AI is feeling like it’s being imposed on people as opposed to them organically adopting it.

And that’s causing people to feel like they don’t have autonomy or agency in their own work, which causes people to stress out. There’s layoffs, there’s a whole bunch going on that leads to anxiety or even fear for some folks.

And the realization I had was, I think everybody is dealing with this on their own.

And we need ways to enable folks to deal with it collectively. So my, my initial thought was, I’ve been writing a little bit about this, for design leaders to, I think, we, we need design leaders to be more vulnerable right now. I keep coming back to that.

People look to their leaders for answers and solutions.

But this is a moment where many leaders just don’t have that. They’re figuring it out like everybody else. But I think those leaders aren’t comfortable acknowledging their lack of awareness or their lack of understanding of exactly what to do. And so they’re pretending like they’ve got it together.

And, but then they ask me, my teams are anxious and frustrated, and what would you say to help unlock those teams? And I’m like ,you need to unlock, right? You need to show that you don’t have all the answers, that you’re figuring it out, so that you’re modeling for your teams that they can be open and vulnerable. I have the Brene Brown book here, ’cause I’ve been thinking about this.

So that they can be open and vulnerable and so that you are all operating with more full information about one another.

And then once you do that, once you share that, or once you discover you have shared kind of challenges, now you can work together to address them instead of everyone feeling like they have to do it on their own.

And I’m wondering, John, how, what you’re seeing in your world when it comes to some of these kind of more existential crises, like last year, even pre AI, you were asking, is design dead? Now in this, not, maybe not specifically pre AI, but AI has definitely accelerated since then, what are you seeing? What are you seeing that’s working maybe in terms of, kind of, leadership approaches that you’ve witnessed that are causing, maybe the temperature to come down a bit?

John: Let me take a step back and build on the point you just made Peter around vulnerability and consternation and fear and those things, those are feelings that don’t only exist in design.

Marketing, finance, supply chain, CEOs, CFOs, all the people that are supposed to be the proud leaders all have their own set of fears and uncertainty. And part of the challenge, there’s not a school or a training program to teach design leaders or anybody for that matter, how to navigate complex political organizations.

Part of the reality around one, one of the reasons I believe vulnerability doesn’t exist broadly in corporations and even agencies and consultancies, by the time people get to a certain level in their company, they feel like they can no longer admit they don’t know something.

So there’s a lot of faking going on. Oh yeah, we’re gonna go do this and we’re gonna go do that. And, or they’re hedging their bets and they’re waiting to make a decision until, the clouds part and the angels sing. So part of this is if you think about… vulnerability is one of those characteristics that infers psychological safety…

Jesse: right.

John: And design and designers are the pent-ultimate people and organization that, that are wired to experiment. If there’s not the safety to explore, they won’t explore and you’re not gonna get the best of people.

And so part of this is basic psychology, basic human resources. But most companies today, especially today with the economic circumstances we’re facing, are faced with the belief that they can’t fail. And this quarter, next quarter is the planning horizon, which doesn’t play well to a designer’s vision horizon, if you will.

Jesse: Right.

John: And so some of this is, it really does take individuals, unless the culture is so good systemically, and as time goes on, I find that there are fewer and fewer of those that have a systemic positive growth oriented culture, because everyone’s trying to cover their backside.

Jesse: Yeah. I think that’s a big piece of it. I think it’s important to acknowledge the emotional reality of the position that the leaders find themselves in now, because I’ve talked with a lot of people in the last year, since the last time you were on the show, John, who have had to figure out how to cut a third of their team and then be the one to deliver that message, even though it wasn’t their idea.

And then they still have to turn around and justify their value proposition to their executives as well as to their cross-functional partners. And the idea that in a circumstance like that, somebody is just gonna blossom into vulnerability as a leader, I think it’s a pretty big ask.

John: And vulnerability is, and perhaps I’ll be a little bit sharp. Vulnerability is viewed as a weakness in many corporate cultures.

That’s a big thing that reasons why people don’t go do that.

But I’ll talk about one, one point that you make. Again, Jesse you talk about these people who are being mandated that they need to go make these big cuts and then deliver those messages. Again, not unique to design.

And so part of that is, is I think because there is the perception and a great deal, the reality that there is a higher emotional quotient among a design community, that there is more empathy and understanding in those circumstances than, somebody that might sit in a in a more linear, numbers oriented, kind of business function, where it’s, okay, these are just numbers. We’ve gotta go do this.

And I think the one, one of the topics that came up in, in last year’s conference was the question was posed: it was first posed as a framing. Look you designers, you play in this empathy space every day. I don’t hear you talking about having empathy for your CEO who has to go deliver some things and the bosses of people who are perceived not to understand what design might contribute. And it, it really was interesting how many people in the room went, oh yeah, could benefit by trying to better understand fears and the pressures and the things that they’re under, even though most of those people don’t seem to openly show and outwardly show fear.

Jesse: Right.

John: And so part of it is, how do we build the tool set so that people have the confidence to be able to stand up and offer okay, we can make these cuts, but here are the likely implications and consequences of those actions.

Just so you’re clear, hierarchy, I’m happy to go be a good corporate soldier and go try to do these things, but if you’re trying to grow, if you’re trying to innovate, if you’re trying to disrupt, if you’re trying to create a culture of curiosity and openness and vulnerability, you probably sever most of those things when you cut a third of your organization.

And I know part of this is about survival.

Jesse: right.

John: About hitting your, the numbers that Wall Street expects. And again I’m being facetious in some of these comments, but part of it is most designers aren’t armed to be able to have that business implication conversation, or they’re not confident in being able to have those things.

And so I, I think it would surprise a business leader if a design leader were to step up and say, okay, here are the business implications if you go do that.

Peter: So generally, I agree with the need for design and user experience leaders to have empathy for the challenges that others are facing and that yes, we’re not alone in this situation.

But a couple thoughts that I’m tying together, one is something you said John earlier, which is like, how it feels like in… Our organizations are decreasingly safe. Like something shifted in, in the last, I don’t know how many years, three, five years where things have become less safe.

And then something that Jesse and I have discussed on a forthcoming podcast, it’s in production, but hasn’t been pushed, is ’cause you mentioned empathy for the CEO, and at least what we’re witnessing is that once you get above a certain level of executive-ness, it tends to select for sociopathy, right? People who do not care about other humans. People who do not see people as people, but as resources, right? I think part of the reason they succeed is they can make a decision, a spreadsheet decision, and they see people cost x and chairs cost y and facilities cost Z and they’re like, okay, let’s get rid of people. That’s a cost we can now reduce or whatever.

And so I want design leaders to demonstrate empathy for their leadership, but sometimes their leadership is toxic and broken and there seems to be a wave of that, like in tech, right? Jesse and I primarily work in tech or tech kind of adjacent spaces, and that those folks have ripped the mask off and demonstrated their toxicity.

I’m curious, again, I’m looking to you to give us a kind of parallel perspective. Are you seeing similar things? Are you seeing different things? Like how is that playing out in, in, in your world?

John: I think the things that you describe are, again, similar if not identical to consumer facing, consumer products, consumer services, finance, healthcare, that the people at the top often that have a letter C before their title or as part of their title.

There, there is this aspect of removing the humanity from the way they make decisions.

And I want to clarify when I say having empathy for the CEO, I’m not necessarily saying you need to go put your arm around them and say, oh man, I feel for you. And but part of this is there’s and for those of out there that might listen to this now or later might, might giggle for those who know me, there isn’t a conversation that exists that I don’t talk about rewards drive behavior and so the rewards of a CEO

Peter: So incentives. Yeah.

John: Or a CFO or whatever are not to make people feel good. It’s a responsibility to drive shareholder value. And for some, a responsibility, I’m gonna be very callousy or a responsibility to drive their own bonus system.

Jesse: Yeah.

Peter: Oh, very much

John: and so part of this is the things that reward them and things that drive them often aren’t values and culture and purpose, unless it can lead to, unless those are things that can lead to other things.

And I say that this isn’t about the way we talk about empathy with users or consumers. Have we walked in their shoes? Do we understand? But there is a need to try to figure out, okay, A CEO that takes over a declining business. Their priority is to turn around the financials the tactical metrics and KPIs of that business, revenue share, profit, shareholder value. There are lots of different ways that to do that.

And I’ll use an example. I had a round table event of corporate side design leaders, and I invited a CEO into the room, and I know this person well, and I said, your job, a, listen to what this group is talking about, what appears to be important to these design leaders, and I want you to chime in when you think you’re ready.

And it was a round table, so it was very organic. When you think something strikes a nerve that they’re helping achieve the CEO’s mandate, or maybe not. And this was back in 2018, 19, so capital was very cheap. Profits were running into the business, quite well, for most companies. Stock market was going well.

And the people in the room were talking about identity and equity and brand and long term and all those things. And this person chimed in and said, everything you’re talking about is important and is needed. But what you need to understand is I’m here to drive shareholder value. And in today’s economy, I could go out and borrow a billion dollars and buy back my own stock and add 10% to shareholder value, and I’ve added more value to my enterprise in 30 minutes than… What you are talking about adding value might take five to 10 years, just took the oxygen right outta the room.

Jesse: Oh, man. Yeah. I think this question of where the value comes from is a really important one because we’ve seen this whole wave of change, especially if you look back like 20 years. Innovation was gonna save us all, right? And every big enterprise was gonna have a big mature design organization at the top that was orchestrating insights and prototypes and concepts and design philosophies that were going to drive product development for decades to come.

But instead, after a certain amount of time, the C levels looked at it and saw a bunch of low value activities. Generative ideation… Why are we, that doesn’t sound like something we should be spending our time on.

Or yeah, you’re going out and getting customer insights, but it’s not really actually driving any kind of meaningful product impact.

And so design leaders now find themselves in the place of defending this, like this sinking island, this increasingly smaller value proposition. And I think for a lot of them they’re wondering like, what? What is the stance that I can take with the larger organization that genuinely speaks to design’s value, but also doesn’t sacrifice design’s values?

John: Yeah. In fact, there are a couple of comments that kind of address that, that notion of, how do I stand up, especially if I’m a lone wolf in my organization. And part of this is, I think, some of this is linked to the skill for a design leader to translate and communicate the work they do into the reward systems and the business outcomes that their business partners are expecting. Can you translate a new product into revenue growth or profit growth or new segment of consumer that we’ve not been able to reach.

One of my favorite requests when I go in and I work with a head of design or a head of innovation or marketing or anybody else, is have you put the big bogey on the table for your senior leaders to, to ponder?

And so for example I was consulting with the head of design of a company that is about 18 to 20 billion in revenue. And I said, what if you were to go into the CEO and the, in the executive lead team, maybe the board and say, I can get you a billion dollars of incremental revenue. Here are the things that need to happen in order for me to help go do that.

So A, if they don’t give you the things that you need to go do that, you can say, Hey, I didn’t get, item four, seven, and nine. But part of this is it gives you the ability to start a business conversation and do it on the context of growth. And, some of that plan, some of that billion dollars may be how do I fix some of the leaky buckets in some of the businesses that we have? How do we create some new things? How do we get into businesses that we’re not currently in?

And it forces the design leader to think about what are the levers that I could pull? What are the levers that I own? And what are the levers that I can assist with that, that I’m gonna need the head of innovation and the head of finance and the head of supply chain to go do some of this, and how do I get them on board?

And because I think the thing that I caution anybody that I… ’cause I get to put this out on the table and then I get to walk out the door, and this…

Peter: yay consulting.

Jesse: Yeah.

John: Person has to live with, oh, shoot, John convinced me to do this, but I don’t know how.

But part of it is the senior most leaders of the company, especially depending on the general health of the company at that time, they’re gonna remember the bogey. They’re not necessarily gonna remember all the conditions to get to the bogey.

And so part of that, is, like any good brand, it’s how do you reinforce when every time you show up?

And again, one of my favorite exercises with teams is every time the design person shows up, you should be asking about the consumer. What did the consumer tell us about this? How did we get to this initiative? What’s the line of sight to the insight that caused us to say that cinnamon was the thing we need to do, or move the button to the bottom of the page.

Apple’s most recent update that moved the search bar to the bottom of the screen instead of the top. It still drives me nuts because I’m not used to it. And, and it’s like what caused them to do that?

But part of this is if you can show up every time, the 27th time, the team’s gonna say, oh, shoot, John’s gonna ask about the consumer. So we better be prepared to answer the consumer.

And I think that gets to how do you reinforce vulnerability? How do you reinforce curiosity? How do you show up that way every day?

And part of it is until you wear them down and then they say, oh, okay, we should be poking around at this.

But I think so many design leaders, whether you are new into an organization and into your career or you’ve climbed the ladder and you’re now leading teams and organizations, we forget about the consistent repetitiveness of some of the things we need to do to remind people.

It’s no different than I grew up in Texas and so everywhere I went Drink Coke was on everything. And it’s on billboards and side of cars and trucks and gas stations and grocery stores.

And the subliminal notion of that is at some point I probably drank Coke because I didn’t think twice about it, ’cause it was in my head.

And what’s the drink Coke, the repeated drink Coke version of some capabilities and activities.

Jesse: Right. When Peter and I were running Adaptive Path together, we wrote a talk together that we called our stump speech, because the whole intention of it was to capture the messages we knew were going to need to be repeated over and over again, and then go out and do that, and each of us gave that talk dozens of times.

Peter: Dozens of times. No, and it tracks with, you mentioned Coke and there is that marketing, aphorism. Basically something on the order of, it takes five to 10 times for someone to hear a thing, for it to actually sink in.

And I think your point stands that many design leaders, we still tend, we have an inclination, we have a tendency to believe the work speaks for itself or the case speaks for itself.

And given what you’re saying what’s this bogey and how are you going to help others understand it? And that you do it once and it’s evident and then if you don’t get acceptance, then I guess they’re just not gonna do it.

And you and many design leaders at that point will give up, like, well, I tried.

And that’s not how this works. You have to beat them over the head with it. And start risking, I don’t even know if it’s risking your own kind of social capital, but like you have to put yourself out there.

Jesse: It is a risk. It absolutely is a risk. Yeah.

Peter: Yeah. And which is something that, as you were talking, John, I had another kind of constellation of thoughts, and one is, you mentioned this bogey and the billion dollars, and I was like, is the issue that we’re seeing with design leaders that they’re not being bold enough. They’re not being big enough, right?

Because design, every design leader I talk to understands the basics of how their work drives business value. And can, good usability means that people can move through the funnel more easily and we’ll see more people adopt or activate or whatever, or good usability encourages retention, right?

Like we, we know these things, but I think it tends to be, it’s incremental, right?

And I’m wondering if what you’re saying is, sure, yes, but you also need, it’s not like a branding play the way you’re talking about it. You need, you can’t simply incrementalize your way to the change you seek. You need to have your brand moment, your pitch deck.

Jesse, I think a little bit about what I imagined Scott Zimmer before Capital One acquired Adaptive Path, and he was the chief design officer and the team was 40 people, and he was like, no, it needs to be 400. And what was that pitch deck?

Or John, I know at your event, Phil Gilbert’s gonna be there, right? And somehow he shook a hundred million dollars out of Ginny Rometti for design. I don’t know what the pitch was. Maybe you do, but is that what we’re lacking? Is a big enough story?

John: It doesn’t have to be a big story, it just has to, I think there’s an aspect of it that has to connect with what are the reward systems of the people that you have to convince to make those investments or to behave differently.

And so your example about usability. If there is a relatively constant level of in of investment that needs to occur to improve usability, remove friction, all those things, but all of a sudden you’re gonna ask for three times that. Now you need to be able to convince somebody why you’re gonna get at least three times better business outcome.

Jesse: Right.

John: And I think that’s the challenge that design has, is when many of them do try to talk business impact, they use the verbal story around impact. Everybody knows if we improve usability, then it’s gonna lead eventually to better outcomes.

But it’s not necessarily obvious to the people who are responsible for driving those business outcomes. And John in the chat talked about, is it fair to say that top line revenue is one of, is a way to have financial impact? Absolutely. It’s one of the easy things to measure, but it’s one of the most impossible things to assign what was design’s contribution to that growth.

And I think that’s one of the challenges that design leaders face is there is an ethical reality to where designers play to say, almost everything we create requires other functions of other teams to go make happen. So I can’t go take credit for that, but as soon as they step away and don’t defend the fortress, then in, in my world, in the brand design world, the ad agency steps in and takes credit for everything

Peter: Our world, that would be the product manager.

Jesse: right.

John: And so I think a part of it is and John I’ll add one more thing that even though this wasn’t what you were asking, is if the business is coming to you whoever you are, marketing design, product engineering, to solve a business metric challenge, oh, we’ve got a revenue problem or we’ve got a market share problem or a profitability problem don’t accept that as the problem.

Those are symptoms of something else.

There’s a reason people aren’t buying your stuff, and that’s the, to me, that’s the real impact that design could have in this is, let’s go understand why they’re not willing to pay a premium, or why they’re, they stopped buying our thing, or why competition suddenly saw a bump in there. And that’s the thing that, that I, I think business people in general are too quick to say, oh, we’ve got a revenue problem. Go solve that. And most of the solutions are gonna look like, oh, we’re gonna take a price increase. And it has nothing to do with solving the underlying reasons why

Peter: Right.

John: something’s not happening or a profitability problem often becomes a cost cutting solution. We’re just gonna go lower the expense side of the equation and increase profitability.

And we had a saying inside of Procter and Gamble, despite the pressure every day to, to save money was you can’t cost save your way to greatness.

And I think Kraft Heinz found that when they implemented their notorious playbook, which was all about cost cutting, but eight years in a row, you can’t cost cut any longer ’cause you’ve cut everything out.

Jesse: It’s interesting to think about how this, you were talking about, Peter was asking about design leaders not being bold enough. And when we think about how we define boldness in this context it sounds yes, it’s about business impact, but it’s not necessarily about scale of business impact, but it’s more like there is a kind of business impact that design as a function can potentially bring that you’re not gonna get from any of your other functions organizationally.

And I wonder if the boldness here is really about asserting a value proposition for your team, for design as a function, that goes beyond what the people around you think your team actually does or can do.

Peter: And to follow on that yeah, ’cause this is something Jesse and I talked a bit about, right, is, and I think about it from an organizational standpoint, design is a function, marketing is a function, sales is a function. Supply, manufacturing, operations, these are all functions.

And as you were saying earlier John, it can be hard for design to identify the value that it is delivering as a function.

Whereas I think those other functions have a more straightforward story to value, right? Sales acquires a customer, cashes that check, marketing acquires a lead. And, that’s the promise. There, there’s, it’s just more direct.

And so I’m curious with your clients, how you help them frame, pitch, communicate, design as a function that’s driving value. What are you finding are the, either the nouns, the verbs the levers that seem to land when trying to present design as this function that is worth standing side by side with these other more mature functions that they already understand.

John: Your use of the word maturity is an important one here because fewer people question a marketing decision because it’s a function that has existed for a long time and supply chain and operations and finance. And design, as much as it has been contributing to the enterprise for a long time, the maturity in which it’s connected to the business is still relatively new, 20, 25, 30 years tops.

And even then, it’s not systemic. Most companies don’t question whether they need to have a chief marketing officer.

Jesse: right.

John: Most people don’t question whether they need to have a chief human resources officer or a chief supply chain officer. But design is still one of these things that, that in today’s world, based on some research I’ve done, design most often reports to a different function and the majority of those people don’t report to the head of that function. So it just reinforces that design is in service to somebody else.

Jesse: Right.

John: And they’re not able to touch the other thing.

So a design leader that reports to a chief marketing officer probably doesn’t have a chance to influence innovation ’cause that’s another chief somewhere that, that is responsible for things. Or influence employee engagement because that sits under somebody else.

And so the principles that could be enacted across those functions could help drive a different culture inside the enterprise.

But it, but by the, because of the way they’re organized, it takes somebody to have to go sell the chief innovation officer that, Hey, we need to put some design people connected to your organization somehow.

And so a part of this is the other example that kind of sparked a thought in my head, Peter, when you and Jesse were talking, is insights. And I’m probably gonna earn an awful lot of enemies and get some hate mail here.

The insights communities that I have seen and had a chance to peek into are more focused on the methodologies of research than what it is they learn from the research. They too are under pressure to cut budgets and do things faster. So internet surveys are way more popular than in-home ethnography or shop alongs because, oh, we don’t have time. We wanna get, we’re gonna put 12 questions out.

And I’m sorry. There’s no way you can phrase any of those 12 questions that are gonna get meaningful insight into innovation work. You could probably validate some things and confirm some things so that you don’t get fired when something does launch. But the learning opportunity, there’s no replacement to sitting next to a consumer while they’re watching, do it, performing an activity on their screen to understand why did you click there and why did you do that? And what are you looking for when you do that?

There was when Proctor and Gamble was in their very earliest journey to elevate design, the CEO, whose idea it was for design to be strategic, A.G. Lafley, he role modeled the behavior he wanted to see everywhere. So when he went to a new market to visit that market, there, there were two things he wanted to do before he got into a conference room to talk about the business.

He wanted to be in a consumer’s home and he wanted to be in a store shopping with a consumer. And then the third thing when he did get together is, what are we doing to serve those consumers?

And then came the business conversation, how’s revenue, how’s share, how’s growth? And so a little bit like my comment about showing up every day, saying the same thing, everyone knew when he was traveling to a market that they knew they were gonna do these things first. They better have their consumer story together and I just have not seen that level of role modeling from a CEO other than the way they happen to role model around finance and numbers and, oh, we need to hit our numbers.

And then one other thing I wanted to touch on is, and this came up in the conference last year, Ken Musgrave, who is a longtime design leader at Ford and HP and Dell, and is now serving at Whirlpool. He talked about the confusion of time horizons and he said, I think about it as a now, near, and far.

Design wants to work on far, but the majority of the capacity of the organization is working on the now or the near.

Jesse: Right.

John: And so part of that is, how might you align the proportion of your now, near, and far in a way that aligns with those priorities of the business.

And the more dire the financial circumstances that the company, the more that is now.

Jesse: Yeah.

John: than it is far.

Jesse: Yeah, that makes sense. The time horizons narrow, right.

John: And it’s rewards drive behavior. We’re gonna drive all of the short term stuff. And part of it is even in those circumstances, if design leaders and designers know that the time horizon is now, hey, that may not be super sexy work, but design could still use their superpowers of reframing something or problem finding before you try to jump in and problem solve around something that you’re unclear about.

And so there, there are still ways to leverage the design superpowers to go drive value and impact in the business. And it doesn’t have to take a big, bold, courageous move to say, I’m not gonna work on that, or, but part of it is, I think, there are a lot of design leaders I talk to say the short term promotion stuff, it’s just not important sexy work.

It’s what if you use that as the pathway to prove what you can do? Go build champions and let those champions then advocate for the periodic longer horizon.

Jesse: It’s often the wrap on design and designers is that they’re so in love with their own craft, that they can’t be bothered to pay attention to the value that they’re actually delivering.

And there are, frankly, a lot of designers and design leaders whose actions have played right into that perception.

I wonder about those leadership skills that we talked about earlier, what do you think are the things that design leaders are most likely to be missing in terms of their own skillset in order to achieve the things that you are describing?

Let’s paint the community with a broad brush here and just call out the stereotypes a little bit. What are design leaders most likely to need to focus on developing within them, within themselves in order to deliver on this promise?

John: The example I’ll use first, Jesse, in, in framing that is, is in the circumstances where I see a design leader feeling like they are under pressure and overstressed, which is most of us, most of them will recess into the project work and become project managers for the work activity, and to some degree completely step away from the organizational side of their responsibilities because it’s comfortable.

That I, I know how to do this, I know how to create stuff,

Jesse: Right.

John: and I know how to get project plans in place and assign resources and all those things.

And I really don’t wanna have to have a battle with the president of the Asia region because of some business pressure they’re under and they don’t feel like we’re solving it for them.

And those are very real and quite more often than you might imagine.

And if any of you are getting to that point, you may not be in your role much longer because the business expects people at a certain level, if you’re senior director, vice president, SVP, EVP, chief, you probably should be spending most of your time on the organizational, cultural aspects of the work, not on the projects, ’cause you have teams and people and agencies and consultants to go do those things.

I think the challenge is the first thing that I would suggest for design leaders is figure out a way to do a self-assessment. To look in a mirror to try to find ways to say, where do I think I’m missing something?

And if you need somebody from the outside or business partner that is willing to work with you and you can develop some thick skin to, to take some feedback, there, there is a self-reflection opportunity.

I think the other is, so many design leaders in so many companies are trying to solve their problems without having outside points of view.

And I just think whether it’s a paid consultant that’s gonna help or a friend that’s go willing to give feedback, that the ability to have a different point of view and a different lens that is not inside of the politics of the company, ’cause that, that to me is where some courage comes from for design, is people that are fractional and are consultants or contractors and things. I don’t care if I’m gonna get promoted or not ’cause I’m not in your culture. So I’m gonna tell you what you really need to hear.

Jesse: Yeah.

John: And too many people, and I see this with consultants and agencies as well, is they don’t wanna upset the client.

So they often will tell the client how smart they are and laugh at all their jokes and tell them how well they dress. Exaggerating of course, but part of this is many of them are not going to tell the client what they actually need to hear because they themselves have become so dependent on the income that comes from that client.

And so there’s this conundrum. Go outside to get candid input, but don’t go to the people that are likely to become dependent on you because they’re not gonna tell you what you really need to hear.

And so back to your question, Jesse. I think establish a vision for where you think you want to go with this. Test it with some people, trusted advisors, friends, colleagues. Create a board of directors for yourself as a leader.

Is it ambitious enough? Is it too ambitious? Are people gonna understand it?

And then find champions. I think that’s another thing that is under-leveraged in corporate organizations is find the people who you have helped make look very good, and remind them that you made them look good.

And some of them, you don’t have to remind them but part of this is they’re likely to go to bat for you. And then one of the other things that I often see, especially if you’re actively trying to elevate design, is, and this is a controversial one, is do not spend a lot of time trying to convince a significant critic.

Go deliver exceptional stuff with the critics, peers inside the company. Other businesses, other leaders, other regions, other functions, whatever that is. And let then let that business, that leader, come to you and say, Hey, how come I’m not getting this?

You mistreated it.

There’s a famous story inside of Proctor and Gamble where the first head of design, Claudia Kotchka, went into one of our business unit presidents and said, I’m taking all of your designers and design managers. And he said, you can’t do that. I can, you’re mistreating them and they’re all gonna quit, and I’d rather have them in the company than for you to stand on pride that you’ve got them.

And she took them and for six months they had to figure out how to go do that work themselves with agencies and marketers.

And they realized they weren’t getting the strategic output that design was trying to reinforce and deliver. And, six, eight months later, it wasn’t a full mea culpa, but it was, Hey, can we talk about getting our ball back so we could play

Jesse: Yeah.

Peter: Yeah. A theme here. And it’s something that I’ve witnessed and try to encourage with the leaders I work with, is I think a lot of leaders don’t understand the power that they do have.

I think particularly design leaders, perhaps because they weren’t in an MBA program, they don’t understand necessarily how these corporations operate, wield or have access to more power and influence than they think.

And instead they tend to get very, submissive isn’t quite right, but reactive or they don’t wanna rock the boat. And they feel like because they’re already, because they already feel like second class citizens, any attempt to stand up for themselves, they’ll will only cause them to get hurt more.

And I, we’re getting close to time and so I kind of like to end around the, the human and emotional challenge that I think these leaders are facing.

I kept coming back to a statement that Simon said much earlier, and I’m putting it in the stream. ’cause this is the thing you can do.

John: Look at that!

Peter: “I’m seeing good leaders stretch to the bones, to the point that they don’t take time to do the creativity work, to put humanistic business proposals together that makes sense.”

And there’s a lot there but I think the heart of it is the, what it says to the beginning, I’m seeing good leaders stretch to the bones.

And this is something Jesse and I are seeing. We’re talking about it with the Liminal podcast, where you’ve got the job that you were hired to do, but now there’s all this transformation occurring and now you’re telling me I need to advance and advocate for design, so it’s even greater, so now you’re telling me I need to understand business and make business cases and there’s so much that we’re being, that we’re asking of folks in order to realize this potential. And they’re just trying to get their work done.

And I’m wondering, John, like I’m sure that with your clients as well. Like how do you help them navigate this opportunity without getting overwhelmed and burned out?

John: I think, I, any please out there, anyone out there, take whatever I’ve said as one dude’s opinion about stuff. But I’d like to think it’s well informed opinion.

But part of this is like the old saying, you’ve gotta, chunk the elephant down into smaller pieces.

So part of it is think about what are all the things that are on your plate. Now that can become overwhelming if I’ve gotta coach people and I’ve gotta manage up and I’ve gotta mentor people and I’ve gotta do this and save money and deliver. But until you, you have a view about what you are responsible for and is that scope of responsibility aligned with what your bosses think you’re responsible for,

Jesse: Right.

John: Until then.

And then the third thing is, how does what you are doing ladder up to what the company is expects as a company? Too many people, I find that they can’t articulate how their job ladders to the company’s objectives and strategies and vision.

And as a leader, you are supposed to be the one that helps people make that connection. And if you yourself don’t understand it, then it’s gonna be hard for you to bring your team along to to say all of that.

One comment I want to add to a comment that was made. Roman, It’s 10 o’clock where you are. Thank you so much for listening in. He makes a comment that, that I’m actually gonna use to promote the conference, is the circumstances that we’re living in today are ripe for design to to make a, an impact and for design to step in and reframe some of the things that we’re all challenged with.

Roman, thank you.

Jesse: John, thank you so much for being with us. Tell us where people can find out more about the event.

John: Thank you. The event, you can go to thefutureof-conference.com, thefutureof-conference.com. The conference is gonna be May 11th to 13th in Chicago. Peter and Jesse are both going to be offering a session and participating in panels at the conference.

The other thing I’ll share is I’ve created a discount code for anybody in Peter and Jesse’s orbit that wants to come. The discount code is Finding Our Way, and you get 26% off. And yes, that’s in an intentional 26 for 2026, but it also rounds out to $650 savings if you want to join and come be a part of the conversation.

Peter: Fantastic.

John: Peter and Jesse.

Peter: Thank you for, yeah, thank you for joining us on our maiden live streaming voyage. Thank you to the folks who listened along and participated in the chat. Thank you to Jesse for putting up with all of this. And we’ll continue to try out new ways of engagement, but until then, it is a Friday before a holiday weekend for many.

So happy holidays. Good spring break. Happy Passover, whatever you’re celebrating. I hope it. I hope it’s great. Take care everyone.

Jesse: Thanks everybody. Thanks

John: Thanks everybody.

Jesse: For more Finding Our Way, visit findingourway.design for past episodes and transcripts, or follow the show on LinkedIn. Visit petermerholz.com to find Peter’s newsletter, The Merholz Agenda, as well as Design Org Dimensions featuring his latest thinking and the actual tools he uses with clients.

If you’re looking for help with AI transformation or you just need a private advisor to help you solve your hardest leadership problems, visit my website at jessejamesgarrett.com to book your free one hour consultation.

If you’ve found value in something you’ve heard today, we hope you’ll pass this episode along to someone else who can use it. Thanks for everything you do for others, and thanks so much for listening.

As of publishing this episode, the Intentional Design Leadership Circle starts in 5 days, on April 15.
https://www.eventcreate.com/e/intentionaldesignleadership
There are still a few spots left.

Also, Jesse announced “AI Transformation for Digital Design Teams,” a new online event taking place April 30.

For more information and registration, head here: https://www.eventcreate.com/e/aitransformation4design

For more about Jesse James Garrett, and his coaching and AI consulting practices visit https://jessejamesgarrett.com/
For more about Peter Merholz, his organizational effectiveness, leadership development, and coaching practices, visit https://petermerholz.com/

Jesse: I’m Jesse James Garrett,

Peter: and I’m Peter Merholz.

Jesse: And we’re finding our way,

Peter: navigating the opportunities

Jesse: and challenges

Peter: of design and design leadership.

Jesse: This is Liminal. When everything is subject to change, how can leaders choose a destination and set the right course? On today’s show, Peter and I return for part three of our exploration of liminal leadership. We’ll get into extracting the signal from the noise of the liminal moment, the role of shared values and collective action in setting direction, and how to make good choices when you can’t predict the outcomes.

Hello, Peter.

Peter: Hello, Jesse.

Jesse: So today we are resuming our liminal conversation. There are little bits of these ideas that have been coming to the surface for us that have led us to this particular conversational series. And now after having spent a little bit of time on the show exploring it, you know, I had gotten to a place where I felt like there are some definitive statements that we can make about all of this.

And then I saw something on YouTube the other day that really kind of shifted my thinking about it, which is that for some reason, sort of out of the blue, YouTube started serving up to me surfing videos unasked for not part my usual rotation…

Peter: Are you sure YouTube hasn’t been listening? Are you sure YouTube hasn’t been listening our podcast?

Jesse: I can’t be sure of that. None of us can be sure of that, can we, Peter? And I found myself watching just, like this stream of live beach footage, which was just, not a big tournament and not your best pro surfers or anything like that, just the beach in a place where they have some really big surf and there are a bunch of people out there on any given day trying to catch those waves.

And what I noticed about watching it was how little of it looks like success in the ways that we would frame success. How much of it is struggle and failure and catching up and compromise. Because what you’ll see out there, if you watch just, like, raw footage of a beach…

Maybe there’ll be 10 people out there with surfboards. A big wave comes up and let’s say six of the 10, the wave just rolls right under them. Like they don’t have a chance, they’re not there and they’re just going to fall off the back of the wave.

Of the rest of them, three are gonna go, not over the wave, but under the wave. They’re gonna get swallowed by the wave. They never get a chance to get their feet on the board because the wave takes them down before they get that chance.

And then that 10th person out of 10 is the one who gets their feet up on the board and they’re up on the board for a minute. But there’s no such thing as a soft landing in surfing. And it becomes a question of, okay, now you are riding that energy, how do you create an exit that feels natural from what you’ve been doing?

And so, the way that I really started to think about it is, first of all, the wave’s not for everybody. This wave might not be your wave.

Like how many waves of technological innovation would you say that you and I have seen in the course of our careers?

You started out working for a CD-ROM company, my friend.

Peter: Careers? We could even go back a little bit further, I started as an Apple IIe kid.

Got a Mac for college. So I went from, command line interfaces into GUI interfaces.

The desktop revolution when I was in college, I had jobs where I used Freehand or whatever to make stuff. And, Microsoft Word, figuring out how to lay stuff out really precisely in Microsoft Word of all things, right? You had to figure out how to hack all the spacing and kerning and all that kind of stuff.

And anyway, sorry. That’s a bit of a, I’m getting, getting nostalgic.

Jesse: Peter. Hey Peter. Get back. Come back to the 21st century please.

Peter: Come back. But you had GUI, and then it was when I was a student at Cal, the web breaks.

Actually I had a job doing multimedia work in school, pre-web. I saw the web. I didn’t work on the web for a couple years, though.

I did work at a CD-ROM company. I then helped that CD-ROM company get on the web. I then worked for a design firm that was moving from traditional design to digital design and web design.

So you have the web, you have Web 1.0, you have Web 2.0, you have mobile, and people forget even before mobile, you remember WAP? Remember when people thought Nokia phones and the Palm Pilot was the future?

Jesse: Hey, I did a bunch of design in that space during that time, so dude, that was real work.

Peter: Yes. I’m I’m sure.

You had iPhone, obviously tablets, the move to the cloud. I already mentioned Web 2.0. And then it’s interesting because, as you talk about waves, there were these actual waves and then there were attempts at making waves. Right.

Jesse: Waves. Yeah.

Peter: Well, yeah, ’cause because pretty much very little meaningful evolved after mobile with the possible exception of things moving to the cloud.

People tried to make something called Web3.0 a thing. People tried to make blockchain a thing and crypto a thing. And the metaverse a thing.

Jesse: NFTs. All the stuff. Yeah.

Peter: Yeah. But yes, to your point we’re definitely now on a wave.

It’s a wave that feels possibly as meaningful as the shifts to web and mobile. Definitely as meaningful, as say, the shift to things like desktop publishing, and putting the ability to create directly in the hands of creators as opposed to needing a chain of labor to get from somebody’s idea to some produced thing.

Jesse: Yeah.

Let’s come back to the notion of liminality and the fact that there’s always another wave coming, right? That the waves themselves just keep on coming.

And in fact to be a surfer is not to find your one perfect wave and then step off the board. It is not just dust off your hands and declare a job well done.

It is more of matter of finding the waves and the waves within waves.

You touched on a couple of things. There are always these technologies that are coming to the surface, or techniques that are coming to the surface.

One of the big things that’s happening with AI is that the technology has reached a relatively stable state, but the techniques around the technology are continually in rapid evolution.

And the big open question, as people look around at these allegedly AI driven layoffs and things like that, is what have those guys figured out over there that we haven’t?

And in fact, the answer is probably not much, but it’s enough to give them a sense of what the future of their organization looks like.

And so surfing the liminality means acknowledging the trajectory of the data that’s right in front of you, right? To be able to read the wave and see where the wave is going so you don’t get drowned by it.

Peter: There’s a parallel here because you’re talking about the kind of these techno waves of technology and change and AI is the most obvious, latest example of it.

I stated how we haven’t really seen a meaningful technological wave since probably the combination of whatever was happening with Web 2, mobile, and maybe a shift to the cloud in the late two thousands, early 2010s.

But that’s not totally right in that in parallel… So those are waves of…

Jesse: Right.

Peter: Society-wide impact. But within our industry, within our field, someone was referring to the waves of design tools that we have embraced going back to whether it was, obviously Photoshop and Illustrator, some of us using diagramming tools like Visio and OmniGraffle.

Then you have prototyping or like early, like some of those, yeah, prototyping tools. Your Dreamweavers or whatever or, earlier web tools…

Jesse: Page Mill.

Peter: But then I… so I got off the design tool train sometime in the Photoshop, OmniGraffle era. I never embraced Sketch. I never embraced Figma. Though I know those have been waves, right, that people have had to ride. I use Keynote when I need to design something.

Jesse: Yeah.

Peter: That’s my little wave off to the side.

But I’m bringing that up to suggest, ’cause you said the word waves within waves, and I think something that maybe gets lost is things can feel very unitary or global or monolithic, right, it’s AI and it’s everything and it’s this one thing that we’re all dealing with.

But the reality is probably that this thing of AI is obscuring a lot of little waves within it that we’re having to figure out and navigate.

One of the things that’s coming up for me a lot in this liminal moment, what’s clear in the discourse is anxiety, and a just a generalized anxiety.

Peter: And part of me wonders if that generalized anxiety is because it’s not one monolithic thing, it’s a thousand little things, and your attention gets frayed. You don’t know what you should be investing your time in to understand and explore. You. start down one path and then you hear this other thing that comes up and you’re like should I do that, or should I finish the thing I started?

And like how to handle all the potential, not noise, but all the potential sources of your attention. And I think a not unreasonable response is just to peace out.

Jesse: Oh yeah. Oh, for sure. Just, yeah. Give into the overwhelm and go to bed. Yeah, I think that’s real.

I think that one thing that I notice in this is the question of what the transition asks of us. Because some of these transitions these past waves of technological change, some of these transitions for some of us asked very little of us, because it didn’t really require us to change our lifestyles. It didn’t really require us to change how we did our work. It didn’t ask a lot of us.

Some of these transitions have asked quite a lot of people to let go of and give themselves over to in terms of… Just think about the digitization of various industries over the course of the back half of the 20th century, and what that asked of every worker in every facility doing every job to engage with different technology that didn’t work the way that they expected, that they basically had foisted upon them by some central authority.

And so this is how automation gets a certain kind of stigma because it feels like something that is enforced upon people rather than something that is offered up as an opportunity or a genuine enhancement to their abilities.

I keep coming back to what this means for leaders, because as you pointed out last time we talked about this, they are the leverage point. They are the point of influence to not just to embrace the new, but also to acknowledge what is potentially left behind that somehow needs to be kept up, right? the fear of this highly automated world is that the soul is lost from the work, that the human voice is lost in the work.

And if no one else is there to defend it, like it’s got to be the leaders who make it happen. They’re the only ones with the influence.

Peter: To defend what?

Jesse: Defend the soul, the spirit the human element. If it does turn into a wall of automation, it’s because we chose to automate things that shouldn’t have been automated.

And so it takes people with the thought and the feeling and the expertise, and as we talked about in the last episode, the background in understanding human beings and the sociological and the psychological grounding to understand what inhumane practices look like in order to instill that understanding in the systems we create.

And I think that applies both internally and externally in terms of not just like what constitutes automated abuse of customers, but what also constitutes automated abuse of your employees, right?

Peter: This is making me realize something that I hadn’t, I guess, acknowledged, come to terms with, which is that I’d been thinking of liminality as something that happens to us, right?

That as you go through life, as things shift and evolve, there’s going to be moments…

I think one of the theses of our conversations is that liminality is always there. You’re always going from something to something else, but there are definitely moments where it feels more heightened and this is one of them. And that’s just the way of the world.

Liminality is a common anthropological frame, rites of passage, certain points in your life where you’re about to step into some new…

Jesse: Seven ages of man, right? Yeah.

Peter: I was bringing some of that thinking to what it means to how we show up as people in our liminal moment and thinking about other themes that we’ve discussed, which is that this uncertainty that we are in can cause anxiety, but is also opportunity, right?

Because discombobulation means people are looking around for someone with some answers to settle things, right? And there’s voids that folks with ideas can fill.

But something you’re saying, and I don’t know the implication of it, but I think it’s definitely worth calling out, is that liminality isn’t simply something that happens to us. Much of the liminal moment that we are in has been imposed upon us by folks who are acting out of their own self interests, but are dismissive, neglectful of the impacts of that decision making on others.

And we’re all having to navigate that. And because when you talk about leader, you talk about power dynamics, and we live in a society where a relatively small number of people wield outsized influence that we all then have to react to. And figure out our reaction to…

Jesse: Yes.

Peter: and that seems to be something different about this moment, maybe than prior liminal moments.

There’s an arbitrariness to it.

Jesse: There are a couple of sides to it.

One thing I’ll say is that I called my business Intentional Associates. You called your business Humanism at Scale. We are both in the business of driving more intentionality in these organizations because I believe that we both believe that if we don’t stand for humanity within these systems, then no one else will, because it is Design, more than any other function, that is invested in bringing humanity to internal decision making.

And that’s what we have seen in our careers as the opportunity for design to create broader cultural change, both internally as well as at the larger social scale that you’re talking about. So there’s that piece of it, first of all Secondarily, there is a certain friction associated with the liminal moment that requires a grace, a fluidity, an adaptive path, if you will, that goes against the way that a lot of people think about their roles. And the way that a lot of organizations think about what success looks like.

And in some ways, when we’ve talked about creating that semi-permeable membrane, that bubble around design, it is in part to enable design to continue to keep that torch lit for humanistic practices.

But it is, I think, a question of that multiplier effect because the perception, the real perception at this point, is that major enterprises are going to start shedding thousands of jobs because they will figure out how to automate away a lot of the work that’s being done by human beings right now.

Regardless of whether we think that’s actually possible with the technology that exists, these technology companies absolutely want us to believe that’s possible because that’s how they keep their investments flowing.

I think that it is for us to answer that question as the upholders, the flame keepers for humanism within organizations, as to how much of this story we buy into and how, much of a counter narrative we offer and what that might look like.

Peter: Yeah, and as you talk about a counternarrative, that connects with something I’ve been thinking about.

Our past two conversations have been very much about what you as an individual can do, or the impact of liminality on you as a person, as you as a leader. How do you develop your own resilience, how do you ride this wave?

And maybe, as a leader, how do you bring others with you?

But it’s still been centered on this kind of individual, not just responsibility, but locus of action.

Jesse: Yes.

Peter: And personal choice, personal decisions.

I’m wondering what the role of collective action plays.

So at the end of the last episode we teased the idea of coming out of the liminal moment. And I think what we’ve realized since then is we may be not quite there yet, but, when you’re in a moment like this, I sometimes call it the Great Discombobulation, right?

You are not the only one being discombobulated. Literally everybody is, at least everyone you know…

Jesse: True.

Peter: …is. And we could all choose to address it on our own, or we could try to connect with others with similar ideals, values, to work together to shape an outcome that is aligned with those values.

You touched on our values of humanism and intentionality. And I think a little bit about the Margaret Mead quote, “Never doubt that a small group of thoughtful, committed citizens can change the world. Indeed, it is the only thing that ever has.” Right?

What does it look like to group, to connect, to look beyond yourself, to realize that others are in a similar situation?

Something I’m starting to see that might be a response, here in the city of Oakland are a bunch of communities springing up, primarily in storefronts, but in other locations as well, right, as a response to a collapse of some structures of community that, perhaps we’ve relied on in the past.

And trying to find ways that people can connect, particularly in a sensitive moment for community, at least in the United States. How do we connect and support one another better?

Jesse: As we pointed out a little while ago, the leader is the leverage point in so many ways because they have the microphone, they have the leverage, they have, in some cases, the direct authority, the check writing authority, which counts for a lot. Money talks, bullshit walks, and if you have the opportunity to spend the money, then you are the person who gets to decide how things go in a lot of ways.

And so if we think about it in that classic up, down, and sideways like you teach in your masterclass, that if a certain amount of the relationship energy is going down, it is creating alignment, creating trust within your team around shared intention. Coming back to intentionality, right?

Intentionality is the way through the liminal because the intentional can hold you together cohesively as a team. When it comes to those sideways relationships, those cross-functional relationships, then it becomes about a desire for certain shared outcomes, right?

We might not have the same worldview as a Chief Design Officer and a Chief Technical Officer, right? We might have different ideas of what the priorities ought to be, but we do have a shared sense of the outcome that we want to create, or hopefully we do.

And that’s part of what a leader can create in the liminal moment that can guide the difficult conversations that unfold in there.

And then, when you’re talking about the relationships upstairs, then you’re talking about, are you reading the same signals that your boss is reading? Are you aligned to the same things that they are actually paying attention to? Because if you’re a Chief Design Officer reporting to a CEO, they are probably dealing with a whole bunch of stuff that is pretty far off the radar of design and you might need to be aware of in order to be able to effectively stay in alignment and not get thrown off the surfboard in that liminal moment.

Peter: As you were sharing that framework, and you mentioned developing relationships cross-functionally, you’re a design leader partnering with a technology leader around shared outcomes, I do believe that potentially a more fruitful path, if you can find it, is to connect with cross-functional partners who do have shared values.

I don’t wanna suggest that the design org is the only one with a certain set of values that others wouldn’t share.

Actually, I was having this conversation with a friend of mine who I used to work with over a decade ago who is a product person. I’m a design person. We had a really strong partnership because we both like to nerd out about organizational solutions to product development problems. And I was talking to him recently, not about liminality, just about, frankly, the broken state of tech.

And so he’s a VP of product and in his org there is a chief product officer. And the chief product officer was leaving and so there was an opportunity that he could ask for a promotion or apply for the role, right?

They wanted to replace that role and he was making an explicit decision not to, and when I asked him about it, what kind of revealed is, there’s kind of a waterline in a lot of these organizations between the senior executive staff and the folks below it. And below the waterline, even across functions, I think you tend to find more commonality, more desire just to like, let’s do some good stuff. Let’s put some good stuff out in the world. Let’s ship good product or whatever. Like an honest and authentic desire to deliver good stuff.

Peter: But above a water line, it starts getting weird and starts getting, frankly, sociopathic. Right? Where there seems to be a selection bias for senior executives around sociopathy. That I believe is because a way that you can be a successful executive is by looking at your organization as not a group of humans, but a group of resources, right?

That’s a sociopathic mindset. And to manipulate those resources, whether they’re people or money or capital assets or whatever, to manipulate those resources for some gain. And you consider people and computers and chairs and buildings to be basically the same. They’re just things on a balance sheet. And those who are willing to go there, are the ones who end up getting promoted into the senior leadership roles because they can succeed in a way that those unwilling to go there find themselves hitting a ceiling where they’re, like, that’s not how I want to operate.

Jesse: Yeah.

Peter: And so I think there are likely folks that you might not realize you have shared values with outside of your organization I think the prospect here is that in a liminal moment where stuff is uncertain and unsettled, if you can find fellow travelers, particularly outside of your function, you can band together, propose things, while folks are in this, ‘we don’t know what’s best’ mode.

If you can bring together a group of folks with a plan for meaningful, positive change, I believe, I might be wrong, but I believe something like that is likelier to be successful now than it would be in a relatively stable context where…

Jesse: Oh, sure.

Peter: …you would just be like, business as usual.

Jesse: Yeah, no, there’s just more on the table right now. If I were the head of product overseeing a product management organization of what I understand to be a typical product management skillset, I’d be terrified about what these new technologies meant for my team, because nobody on my team can actually write requirements to the level of specificity required to actually execute.

But you know what? My design partner’s team might. So I think it’s a very real opportunity to build bridges, especially at the leadership level. But I think that to your point, it might not be at that, like, the sociopathic C-level, which I have to completely agree with. It feels like that’s what gets selected for, right?

And what you end up with is that, yeah, everybody with a more humanistic bent hits a ceiling somewhere along the way that prevents them from gaining more authority.

But you mentioned shared values and I think that’s an important piece to bring into the conversation.

I talked about shared intentions with your own team. I talked about shared outcomes cross-functionally, and I talked about shared awareness with executive leadership to show that you were following the same signals that they were following.

But I think there is this deeper question of, are we on the same page in terms of where we see this going? Not just from a metrics perspective, but in terms of the shape of the organization that we’re leaving behind.

There is I think, not enough attention to legacy in leadership broadly. But especially in navigating the liminal, like if you are genuinely trying to set a team up for some future, regardless of how clearly you can see it, it’s still on you to leave it in a shape that they can actually execute on, right?

Peter: Agree. I don’t have much to add to that.

And I find myself realizing that you and I might be falling into a bit of a trap with an assumption that the path forward is within the context in which you’re currently operating and trying to make sense of that space, and to navigate that space, and in this liminal moment maybe set direction within your current organization to help bring clarity to all that uncertainty.

But that could be a trap, right? A potential way forward, and we’ve seen this pattern in prior cycles, is that small group of people with shared values in your organization, leave that organization and do their own thing.

And there’s an opportunity theoretically right now, right? Given what we were told about these tools, to let a thousand flowers bloom, right? And maybe, the outcome, or an outcome of this liminal moment, well, an outcome of this liminal moment is…

It was with Jorge, we talked about the K patterns, right? Where the, the poor get poorer and the rich get richer.

A similar thing… ish? Is we see either: Fewer massive enterprises, right? Those that can just capture the space we’re in and the value therein and it becomes, Weyland-Yutani type shit.

And or a thriving marketplace of three to seven person businesses solving problems in a way that they couldn’t have sustainably done before for whatever the economies were, but now maybe have a greater ability to do so, to opt out of a giant corporate ladder climbing game and into a… I mean, I’m starting to sound solarpunk or something here, right? But, into a more emergent, I don’t wanna say the word artisanal, but I’m saying the word artisanal, distributed, hopefully gloriously chaotic as opposed to painfully chaotic, flourishing.

And I say it’s happened before, right after the dot bust. It took the dot bust and the wounds licking and the playing around with technologies. Adaptive Path emerges from the dot bust. Core early technologies, Flickr comes to mind, Facebook, a lot of the things that have now are dominating, kind of emerged from this period of firmament that occurred in that downturn.

I don’t want our thinking to be constricted, to playing forward the current situation or the current context, and instead recognize because we don’t know where this is going, we are freer to imagine other potential outcomes that might be more aligned with our values.

Jesse: Six outta 10 people don’t get on the wave, and maybe they wanted to get on the wave and they just couldn’t build up the energy necessarily to catch the wave. Maybe they just realized it wasn’t their wave and they let it go under them, and maybe the wave that’s happening in your company right now isn’t your wave right?

Maybe they are deploying these technologies in grossly irresponsible ways because they haven’t intentionally developed an AI transformation program and maybe they are advocating for things that don’t align with what you signed up for, what you even thought your job was going to be.

All of that is okay. It’s okay in a couple of ways. First of all, this is gonna be something that is gonna take a long time to make its way out. The ripple effect is going to continue from these organizations that are closer to the center, first of all, which are these organizations that are frankly under VC pressure to adopt certain technologies and meet certain metrics in their own growth.

And then you’ve got the companies that model themselves on those guys, which we already know about. Regardless of the right or wrong of how they’re actually doing things.

So then from there, you’ve got a whole long tail out from there of other organizations that are gonna be adopting these technologies at their own pace. I can imagine you can continue to basically, continue with business as usual, in the exact same way that you’ve done the job as a design leader for the last 10 years.

You could probably do that for five to 10 years more, easily, before it gets to a place where you start to run out of places that do things that way, because the tooling has evolved. Maybe not 10 years, maybe that’s too optimistic, but.

Peter: I think this is important; overlooked. We’re in a moment of such kind of anxious intensity where it feels like we have to change now, or in the next three months, and if we’re not, we’re gonna fall way behind.

To remember that these things take time, that every change that has felt like it was going to be immediate took time. As you were talking, I was reflecting on how most businesses still don’t build software well, even though we’ve known for 20 years how we should do it. We just ignore it.

That and, like, the agile revolution was some similar kind of upheaval internally for a lot of organizations.

How’s that borne out?

Jesse: Mm-hmm. Mm-hmm.

Peter: Many companies still really aren’t.

Peter: And the thing though, that we haven’t talked much about, is if this is gonna take time, people can’t maintain their current level of anxiety, energy, whatever that buzz that we’re all, that we’re all feeling.

It’s gonna burn them out.

And this is something that in my own, just personal kind of thinking through what it means to show up in this liminal moment, I’ve been wondering about, which is, how do you not burn out when everything is always feeling anxious?

Now you’re telling me that we’re gonna be doing this for five years or something. That doesn’t make me feel better. I’m gonna feel like I’m feeling today for five years. Is that what that means? There’s something about…

Jesse: That’s not what I meant.

Peter: I know it’s not what you meant, but there’s something about this, like, navigating liminality is frazzling, right?

Because of that uncertainty.

Jesse: It’s exhausting. Yeah.

Peter: I feel that as a solopreneur, operating in six or seven spaces and I’m constantly task switching and I never quite know what the next thing is that I’m going to be working on.

And so I have to be ready for a lot of potential opportunities depending on what turns up in what direction, and that’s exhausting.

And I’m curious, this might be something that you have some more formal, or at least mature thinking about, born of a coaching practice. ‘Cause I’m sure this is something leaders deal with all the time, which is managing their energy, managing a pace, cadence.

Right. A leader always has, even before a liminal moment, leaders always had more work to do than they had time to do it.

In a liminal moment that feels like it’s like everything else: accelerating.

How do people manage their own, energy, resources, so that they don’t burn out. When they’re in an environment that just feels like it continues to apply pressure.

Jesse: I think prioritizing your attention is a fundamental skill for leaders.

The ability to, as much as possible, shut out everything that isn’t the decision that you need to make right now, and be able to really let go of it until it’s time, and to trust yourself that you will create the time and create the space for that decision, and that you’re prioritizing the right things.

And if you don’t have the mental systems in place to prioritize the right things, yeah, you’re gonna be constantly scared that you’re spending too much time on the wrong things.

So I think that’s a huge piece of it.

To go beyond the surfing metaphor and look at something like sailing. Imagine that the leader of a team is the captain of a ship, right? And you’re standing on the deck of the ship and what are you paying attention to?

You’re paying attention to the information that’s coming up through your feet as the boat is rocking in the water, and you’re paying attention to what you’re seeing from the waves and the clouds and the other stuff that’s coming in, and you’re paying attention to, what you’re feeling from the wind that is gonna tell you how much attention you have to give to where we put the sails and where we put the rudder and where we, how we deploy the team to get the ship to where it’s going.

So if you’ve got calm waters, if you’ve got people that you can trust to keep an eye on the mainsail and all the rigging and the stuff, yeah, you can go downstairs and you can take a nap.

But if you don’t have those people, you can’t.

Peter: I like naps.

Jesse: I said Peter’s magic word.

Peter: Thinking about navigating this moment collectively.

A week or so ago, I wrote in my newsletter, what I’m calling the design management quality cascade, and it’s a response to witnessing VPs of design reviewing, like, delivery work in an organization of more than a hundred people, right?

It’s not like it’s a 10 person organization, that makes sense, but when there’s 150 people in the organization, the VP should not be reviewing delivery work.

But it was happening and it was happening for a number of reasons.

What the design management quality cascade lays out is how to locate the appropriate responsibility at the appropriate level, right? So you’re talking about the captain of the ship and there’s a certain set of things that they’ll be responsible for, and then they’ll have, I don’t know all the terms on a ship, but they’ll have their leaders reporting into them who’ll have their responsibilities, and people reporting to them…

And on a ship, this I do know, everyone knows exactly what their specific responsibility is. the ones I know In a design organization that almost never happens.

And so what ends up happening is that VP, that captain, ends up doing a bunch of work that they probably shouldn’t be doing. They’re not prioritizing well, to use your language, because they don’t know… they either don’t know or they don’t have the confidence in the people in their organization that they’re actually doing the thing that they should be doing.

And so they feel like they need to do it all.

Jesse: Yeah. Yeah. They don’t have people that they can turn their backs on. They don’t have people that they can trust to make decisions without them. And that’s what it comes back to is, like, how many decisions can you actually let go of so that you can give the maximum time and space and attention to the decisions that actually matter that only you can make.

Peter: Well, and that becomes exceedingly acute in a…

Jesse: Exactly so, yes.

Peter: Right? Because… because, a liminal moment, you’re going to be making new decisions, right?

Most of the time when you are making decisions, you’re making decisions where the outcome is somewhat predictable, right? And it’s usually choosing between trade-offs. We could go path A, we could go path B. Path A has this, path B has that. We know where both of those paths go. And your job as leader is to help figure that out.

In a liminal moment, you don’t know necessarily the results of those decisions.

Jesse: Door number three.

Peter: Though you are probably best situated to hypothesize, right?

Actually, probably the nature of the decision depends on the level of the organization, right? But at that senior level, because of the context you’re in, because of the information that you have access to, you understand a likelier outcome of decisions at a certain altitude.

Jesse: The more you expand your awareness as a leader, the better informed your decisions are. Full stop, right?

The more different sources of data that you are taking in, the broader range of the organization that you’re in connection with, you’re just gonna be more broadly informed.

And that’s what I mean about building shared awareness with your executive leadership because they have to be informed about everything. And if you are ignorant of two thirds of what’s going on in the company, because you’ve been paying attention to your own little corner, your value prop isn’t there as a participant in actually guiding the organization.

Peter: There’s gonna be multiple reasons of your ignorance, but if, a reason for your ignorance of what’s happening in the C-suite is because you are involved in decision-making in the, lower levels of your organization, that’s a bad use of time.

And so delegating responsibilities, placing trust in those people within your team, empowering them to make the decisions that they are closest to and should have full information on, frees you up as a more senior leader to tackle a kind of decision making, a different kind of decision making, where there is a risk involved, because there is an uncertainty and an unknowingness.

I’m thinking also about… it should be at that executive level..

Jesse: Yes.

Peter: Because you mentioned the power of the purse, right?

And this is something else, too many design executives don’t understand the power that they have, but that you get with being a vp, that you should have budget and budgetary authority. You get to make decisions, you get to carve out time to do things.

And I know that in many organizations, VPs have become disempowered. That’s a separate conversation. It’s an unfortunate one. But not just design VPs, like VPs across the board, like the C-suite holds very tightly to all kind of meaningful decision making.

Let me get back to my original thread, which was as a VP, as an executive, you should be able to initiate programs of discovery to sense your way through the liminal moment, right?

You don’t need to know where you’re going. None of us know where we’re going. But you have the means to…

Jesse: Read the wave.

Peter: Better hypothesize, to read the room, better hypothesize, and then place some bets. Yeah. To put probes out there, and then based on the information you get back from those probes, do the work of directing the organization towards healthier outcomes.

Jesse: That’s what I think is central to a leader’s value proposition, is the ability to generate from their own perspective, from their own point of view, those sorts of explorations.

If you don’t have the power and the permission to do that, I don’t know.

I don’t think any organization really just wants reactive leaders. I think on some level it has to be a part of what you do, that you scout for opportunities for your team to deliver new value and different kinds of value, and to continue to drive and explore that.

I don’t know, that’s me.

Peter: No, I think you’re right. I think you’re right. I think too many design leaders are reactive. They’ve gotten in a do what they’re told mode. That started with this mindset… I still hear from design teams that use briefs. ” We gotta receive a brief and then when we receive the brief, we now can respond to that, we know what to do.”

And I’m like, What? What…uh, briefs? No, no briefs. Full stop. Because briefs mean, you’re in service to, not in partnership with.

And when you’re in service to, you are not leading right? You are only reactive.

And if you want to make change, you need to shift that posture to one of problem identification and exploring solutions.

And as you were talking, a theme that’s been true about all this AI shit since we started talking about it is, because AI is an accelerant, kind of more than any other thing, what it does is it reveals cracks in…

Jesse: Mm mm-hmm.

Peter: …Organizational practices, that maybe had been filled in, or you could paper over or you could kind of ignore. But now with that accelerant, those cracks are starting to strain and break, if you haven’t been doing the right thing.

And I think what you’re talking about, what we’re getting to here, is that basically nothing we were saying about what a VP should be doing is new. This is what VPs should have always been doing. The difference now is when VPs don’t do the things that they should have been doing, the outcomes are magnified.

Because, let’s say, you’re that VP who’s looking at work, is too focused in the weeds. And thanks to AI, the amount of work that your teams are doing is accelerating. So now you’re just gonna be in the weeds more, right?

Which means you’re spending even less time with the executive leadership that you should be partnered with, right? That kind of thing.

Jesse: Yeah. In the same way that, as we talked about when we talked about the Elements of UX in the Age of AI talk it’s not just that it amplifies the existing value proposition, but it also magnifies the places where the process is not optimized. And those things are gonna continue to be coming to light for teams within their own processes.

You know, when I think about what all of this means for the liminal leader, so to speak, it does seem to entail a willingness to hold your own perspective while continuing to listen to others. Maintaining those connections with other viewpoints because, to your point about collective action, the organizations that are going to hold together through this are the ones that have the strongest shared values and shared practices and shared beliefs.

Otherwise, I think you’re right. People will spin off and do their own thing and maybe some of them will see this as an opportunity to move to a smaller place that is gonna be really lazy about adopting all these new techniques and technologies. And they can continue to build websites with Quark Express for as long as they want.

And there are other people who are just gonna get the hell out, right? And go open a pottery studio in Alameda or something like that.

Peter: And that’s been happening. Bakeries.

Well, Yeah. And a thought I wanted to make sure that got out, that I think captures a bit of what you were just saying, but something that I’d written down before we spoke: liminality is not about a destination.

You’re talking about: what does it mean to be a liminal leader? To be a liminal leader is you don’t know exactly where you’re going. So it has to be about the journey.

But, and this is tricky. It can’t just be random. You’re not just stumbling around. There is a direction that you’re moving in.

Liminal leadership needs to have confidence that even though you don’t know exactly where you’re going, you’re moving in generally the right direction, wherever that is.

Jesse: So this is where the three out of four people who get on the wave, get swallowed by the wave, because they misjudged where they were relative to the wave and weren’t paying attention to the right things. And they went under instead of over and didn’t get up on the board.

And what you’re talking about is really the ability to get up on the board, so to speak, to be able to calibrate yourself to the moment and activate in the moment when the moment arises.

Am I overextending the metaphor? Maybe.

Peter: No, and I think this is good place to end.

The thing I just realized, and I don’t know if that was always part of your intent, was that of those 10 people, it’s not the six who never got on the wave that are struggling. It’s the three…

Jesse: Thought they could catch it!

Peter: …Who thought they were ready and weren’t. Those six are actually better off having let that wave go by ’cause they weren’t ready for it, right?

Jesse: Yes, that’s exactly right.

Peter: So it’s having that, we talked about discernment with Dan, right? There’s a discernment here of your moment, right? And this is that prioritizing conversation as well. You need to be self-aware of what is your moment and what isn’t and with some of those surfers there was a misfit between what they perceived and their ability to take advantage of it, and they didn’t succeed.

Whereas those other six on subsequent waves might have been able to have a perfectly good ride.

Jesse: Yeah. Yeah.

Thank you so much for the conversation, Peter. It’s been fun.

Peter: Yeah, this was great. Thank you, Jesse.

Wow.

Jesse: For more Finding Our Way, visit findingourway.design for past episodes and transcripts, or follow the show on LinkedIn. Visit petermerholz.com to find Peter’s newsletter, The Merholz Agenda, as well as Design Org Dimensions featuring his latest thinking and the actual tools he uses with clients.

If you’re looking for help with AI transformation or you just need a private advisor to help you solve your hardest leadership problems, visit my website at jessejamesgarrett.com to book your free one hour consultation.

If you’ve found value in something you’ve heard today, we hope you’ll pass this episode along to someone else who can use it. Thanks for everything you do for others, and thanks so much for listening.

For more about Jorge, visit https://jarango.com/

For the Claude skills he discusses, visit: https://github.com/jorgearango/llmapper-skill

To learn more about Jesse and Peter’s Intentional Design Leadership Circle, starting April 15, visit https://www.eventcreate.com/e/intentionaldesignleadership

To join the first Finding Our Way Live! on April 3, visit our event page on LinkedIn: https://www.linkedin.com/events/7442678896506068992

Jesse: I’m Jesse James Garrett,

Peter: and I’m Peter Merholz.

Jesse: And we’re finding our way,

Peter: navigating the opportunities

Jesse: and challenges

Peter: of design and design leadership.

Jesse: On today’s show, consultant and author Jorge Arango is our first return guest, five years after his last appearance. We’ll talk about his current work in AI transformation, how AI has evolved his thinking on the craft of design and where information architecture still plays a role in this new landscape.

Peter: Jorge, welcome back. It’s been five years since we’ve last had you on the show.

Jorge: Fortunately it’s not been five years since we’ve talked. But I’m so excited to be back in the show.

Peter: Awesome. You are our first return guest. Five years ago, it was deep in lockdown, heart of the pandemic. We talked to you about some themes that are still relevant today, craft, practice. We were interested in your architectural background and how that was helping you think about design and design processes you were teaching at the time.

So you were very meta around your thinking and we wanted to tap into that, but it’s five years later. Which feels like a lifetime, particularly after the last couple of years. So what’s going on with you? Where are you at? What you up to? How do you talk about what you’re doing right now?

Jorge: You know, talking about five years, it makes me think that about five years ago people were tossing around the phrase “the before times” to talk about like the before the pandemic, you remember that? It’s like, “Back in the before times…”

Jesse: Right. “Before what?” anymore.

Jorge: Yeah, that’s the thing, right?

Like that phrase is, like, we keep using it. It feels like we’ve left the world behind, right? Things started changing significantly back in 2020. I mean, I feel like things had been changing even before then…

Jesse: Oh yeah.

Jorge: 2020 was a big inflection point with the pandemic. It moved so many people and processes that maybe had resisted going online. It moved everything. We were working remotely and all that stuff. We still are.

Jorge: But then obviously, the breaking of AI into the mainstream as a thing that people are concerned with, interested in, trying to find how to use, is the latest catalyst, I think, in casting the past as the before times.

And as many people have, I’ve been trying to find my way in this new world, and I find that for me it’s about coming back to fundamentals, to first principles, to what is it that I’m uniquely suited to help add value with? And I’ve been on a path of rediscovering that, and I’ll say this right up front, I’m more excited about the work than I have been for a long time, as a result of all these changes.

Peter: What do you call the work? What do you mean by “the work” when you say that?

Jorge: Y’all know that Harry Max and I are doing a podcast. And Harry has this definition he’s used this in a couple of episodes. He has this definition for stupidity that I really like.

He says that, I’m reading now from one of the transcripts here, “Stupidity is a result of a series of decisions and actions that lead to results that are the opposite of the intended outcome under conditions of self-deception.”

Peter: Okay.

Jorge: So basically self-sabotage, right? Like, it’s like…

we,

Peter: I didn’t realize your podcast was about our current United States

Jorge: Well, this is like the discovery for me. You asked what’s the work? I’ve realized that my work boils down to helping people and organizations, particularly the people who have the most leverage, act intelligently.

Like, I bring up Harry’s definition of stupidity because that’s what you don’t want, right? You don’t want self-sabotage. You don’t want to declare that you are trying to do something and then end up with the opposite outcomes. And we have this catalyst in our midst, AI, which can either help or hinder our efforts to act intelligently.

And my work now is focused on… the way that I describe it in my website is, like, What’s the architecture of intelligence? Like how can we use this information that we have available to us to act more skillfully? And you won’t be surprised to hear that I think that, first of all, letting in the right information and then carefully structuring that information is a big part of how we act skillfully.

Jesse: So, you know, the three of us all met through the information architecture community back in the early two thousands where there was a real energy and focus building around the idea of, if we could just structure enough data in the right ways, we might be able to create systems that were better for humans.

And that, I think was the, continues to be the, innate promise of information architecture as a discipline. Now, and honestly, this was predicted by IA people. It’s so funny because I can’t remember who said it. I think it might’ve been Lou Rosenfeld. I think it might’ve been Peter Morville, I can’t remember which of them it was, but I feel like it was one of those two guys who, at some IA Summit said, we’re not going to crack the AI nut until we crack the IA nut.

And the idea being that if we master the structuring of information itself as a human discipline, then we will be capable of creating the intelligent systems that we actually need, that will actually serve us. And it feels like a lot of your work in the last year or so has really been moving toward that.

I don’t wanna project onto your career something that isn’t there, but I’m curious about, like, how do those ideas resonate with the work that you’re doing now?

Jorge: Yeah, they absolutely resonate. the way that I’ve articulated it, at least in my website, is that information architecture can be done more skillfully with AI. But conversely, AI can be better if the information that it’s fed is carefully architected, right? So, I’ve been trying to play kind of both sides of that.

Say, it’s like I work both sides of that loop, right? I’m trying to like understand how AI changes the work of structuring information with the understanding that the better a job you do at structuring the information you feed, particularly language models, the better the outcomes you’re going to get.

There’s work above that, which is like trying to figure out, like, what are the outcomes that we’re trying to get out of this? And you talked about, like, human goals that ostensibly you want to design systems that produce better outcomes for people and for society and that help drive us forward, and there’s a technical conversation about like, how do we structure systems to help us achieve our goals?

And then there is a broader conversation about what are our goals, you know, what are we trying to do here? And that has to be informed by a clean read on the context. Like where are we? What’s going on? What are our competitors doing? What is our organization aspiring to? Like, there’s all these things that stand above the technical discussion about how do we architect information, how do we architect AI or what have you?

Jesse: I guess when I think about our audience and I think about design leaders and the pressure that they are under, in a lot of ways it is about simply having a story to tell about where this tech fits in as you see it as a leader, within your organization, within the boundaries and the constraints of what is expected of your team.

And in some design teams that expectation is super tactical. It is pixels and Figma and, moving the data into production. And on other design teams, it’s not that. There’s a lot more sort of strategic permission to engage with the bigger ideas behind the product.

And I’m curious about your perspective on how those things play out in the choices that design leaders have to make around where they focus their attention because their attention is spread so thin, right? It’s like, where can I pay attention to this tech where it’s actually gonna matter and it’s actually gonna create some traction for the team against an actual value prop.

Jorge: I think you framed the question correctly by stating upfront that there are different understandings of what design is, right? And I suspect that in a large number of organizations, design is seen as a production function that involves cranking out screens. And if that is the sense in which design is understood in a particular organization, the design leader will have a different engagement with these new technologies than in an organization where design is more, I’ll be judgmental here, more correctly seen as a more strategic discipline.

So let’s acknowledge that right up front. There’s an information architecture labeling problem there with the word design.

My sense is that it might not be worth a leader’s while to try to reframe the organization’s understanding of the discipline through rhetoric, through persuasion, right?

You’re working in an organization where design is seen as a production function, your best strategy forward might not be to try to convince your colleagues that’s not a good reading of what design is. You might be better served by trying to prove designs value within the constraints that apply to that particular organization, right?

If the organization sees it as a production function, then try to produce it as effectively and efficiently as possible.

Jesse: So this suggests tuning your approach to AI tooling toward the value prop that is already expected of you, right? On some level.

Jorge: There’s a step before that, which is, taking for granted that the design leader understands the context that they’re operating in. That might not be true, right? Like you might have expectations of what design is that are misaligned with how design is actually expected to function.

And again, you two have worked more closely with design leaders than I have, coaching them and stuff like that. So you might have more to say on that.

Peter: I have a lot to say about that.

Jesse: Yeah.

Peter: I wanna set aside the understanding context bit, which is important.

Jesse: For sure.

Peter: So Jorge you mentioned the challenge of rebranding design, it is commonly understood in some fashion internally. This is a challenge that nearly every design leader I work with faces, it’s at the heart of my masterclass and one of the core tenets of my class is you need to meet people where they are at in their maturity.

You as the design leader, are always gonna be way more mature than the rest of the organization about design. And if you try to accelerate or put forward your design approach into an organization that’s just not ready to receive it, you won’t get anywhere.

This gets a little bit back to something Jesse and I used to talk about years ago. When Jesse had this idea of the three maturities.

Jesse: Right.

Peter: I don’t think the idea though is simply to then give the people what they want and stop there, right?

That’s where you start, because folks around you have a set of expectations. If you don’t meet those expectations, they will then just dismiss you. So you need to meet their expectations, but you also then need to have some idea of where you want to take things, which as you meet their expectations, the theory goes, you demonstrate your credibility, the more credibility you’re demonstrating, the greater trust you’re earning, the greater trust that you earn, the more that you can then start bringing people with you.

But there’s a journey you need to go on. You can’t just again hop the queue or hop the maturity model and say, we should be operating at maturity level five. We’re at two. Let’s just go. You need to take the steps. You need to take the steps through it.

Peter: I wanted to actually get back to something else you talk about, which is related, which is something that’s becoming clear as I read about AI and talk to my clients about these AI tools, is that perhaps the biggest gap, shortcoming, that teams are facing is a lack of clarity on the part of their organizational leadership, their senior most leadership. And without clarity as to goals, outcomes, mission, vision you get a lot of chaos with AI, ’cause you basically accelerate the current chaos.

Jesse: Amplify the noise rather than the signal. Right?

Peter: Yeah. And I think that’s starting to stress people out as, like, a lot more stuff is being done. But you also hear that people don’t feel like they’re doing better work. They’re just doing more work.

And I think the reason they’re not doing better work is there’s a lack of clarity as to what are those goals, what are those outcomes? What are we aiming for?

And so I’m curious, Jorge, it sounds like you’ve been doing a fair bit of work consulting with Greg and your practice with organizations. Are you, how are you helping them achieve clarity, or what is your relationship to the clarity story here?

Jorge: The three of us were working when the web happened, right? And that was a time of big change. Like now, that was a time when people were excited about a new technology and looking for ways to apply it. There was a lot of hype, there was a lot of misunderstanding. I remember, like, trying to explain the web to people and getting glazed looks, right? Like, what are you talking about?

And it was a time when there were a lot of solutions in search of a problem to solve, right? And people were putting the technology forward because it was like an exciting new thing. And in many ways, I feel like we’re in a repeat of that, but even perhaps more impactful than what the web was in that this feels like the ultimate general purpose technology that we can now apply to anything, right?

Like, it’ll just solve all your problems because it’s artificial intelligence and it’s so much smarter than people and all this stuff. And there’s a lot of misunderstanding about what the technology is that is very similar to the kind of a misunderstanding that we saw in the early web. Recently, I reread, do you remember John Perry Barlow’s Declaration of Independence of Cyberspace?

Jesse: Oh very much. Yeah, sure.

Jorge: Right? You go back to that and you read it and you’re like, man, you remember that kind of naivete that we had at the time?

It’s like it’s going to change the world, like nations of the world, stand aside. Here we come. There was this notion that this technology was going to somehow overcome human foibles, it’s like technology never really does that, does it?

Technology can amplify human

Jesse: Yes.

Jorge: You know, it’s understandable that we are now in the thrall of this new thing and therefore acting unskillfully in many ways. I suspect that needs to burn out and it will burn out. What I wanna do is, I want to help organizations and the people who are leading organizations use this new technology as skillfully as possible.

So like, how do we speedrun the path to a skillful use of the technology, meaning free from the delusions that come from our projecting into the technology capabilities that it doesn’t really have. Which in this case are quite tempting because it is, first of all, there’s been a lot of hype, and second of all, frankly, we work with the technology day to day, and I’m continually impressed by its capabilities, right?

Jesse: Yeah, no, the line is really fuzzy, right? Between what it can do and what it can’t do. In part because we are still exploring the boundaries of what it can do, but also because that’s changing. It’s been fascinating.

So my first vibe coding project was about like two years ago where there was no tooling and there was a lot of kind of figuring things out as I went.

And then to see this stuff fill in where there’s more and more support, there’s more and more understanding of the use cases, and this is where it actually gets exciting when we think about the application toward, going all the way back to what you were talking about, the value proposition of design and what design has to offer and what design has to bring.

Jesse: So the opportunity potentially is on both sides, right? On the one hand yeah, on this show we’ve talked about a few times, the fact that we are now sitting on a bedrock of 25 years of best practices of active user experience teams in organizations, building up understanding about baseline human experience kind of stuff when it comes to 2D pixel interactions, right?

And then you take that into a space where a robot can meet that baseline. And then I think you start to get into some really interesting territory because, on the one hand, there are a lot of problems the robot can solve that no human…

You could hire somebody to do that job and they would do that job well, I’m sure. And at the same time, they will be discovering nothing new. They will simply be reiterating something that has existed before. So it’s like UX, bricklayer kind of a role.

And then the other place of it, potentially, is that the robot helps you see something you didn’t see before about what’s possible and whether it can ever go beyond best practices. I did this talk last year, the Elements of UX in the Age of AI, and I talked about the fact that from my perspective what it will always be best at is mediocrity. And so what does that mean for the role of the designer in all of this?

Jorge: I wanna pinch and zoom on what you’re saying there, because what we’re being called to do, and now I think that we’re addressing perhaps practitioners, right, as opposed to like design leaders who tend to get ensnared by their identity as a practitioner of a discipline, right?

Maybe I’m speaking of myself, right? As opposed to I don’t wanna project on other people.

But one analogy that I’ve been using when talking about this stuff, and I’m sure it’s not original to me, is the trajectory that computer programmers have been on.

So the original, the initial digital computers, you programmed literally by flipping switches, right? Like you had to understand binary math. And you had to understand the user interface of the system, the way that humans programmed the computer involved thinking like the computer because the interface consisted of turning certain registers on and off.

And eventually higher levels of programming were invented where you had things like assembly language, which allowed the programmer to think in terms that we’re more human-like as opposed to like machine-like. And then if you want to go like a level of abstraction up, then you start getting even higher level languages, right? Things like when I learned computer programming in the early 1980s, it was BASIC, right? And it was called BASIC for a reason, right? And it was mostly English, highly structured English, but it was mostly English. Like I was not having to learn op codes.

Jesse: Right.

Jorge: And what we have now in that analogy is now you don’t even need to worry about things like you know, these higher level languages. Now you can just describe the thing that you want. And this is a progression of ever higher abstraction away from the way that the machine works at its core.

Jesse: Right,

Jorge: And the question is, how many challenges that we were used to flipping bits for, can we now abstract away from, because that’s what we’re being handed here. We’re being handed, like, some ways it’s like the ultimate abstraction machine.

Jesse: Yes. Yeah.

Jorge: One way to think about the implications of that for something like a design team is, you were used to sweating the details around things like the corner radius of buttons, right? And ensuring that those things were being applied consistently throughout a, imagine like a large suite of software applications.

And you know what, if you’re freed from that constraint, what if you no longer have to worry about that? Because you have systems that are abstracted enough where you can be sure that the details are going to be looked after.

And now you, the human setting direction, can focus on higher level directions, right? And you can develop new patterns.

So here’s an idea from software development, and I don’t know if this is true, but it’s my kinda read on the thing. I don’t know that you can come up with something like object oriented programming if your thinking is happening in bits. Like you have to think about what you’re doing at a higher level of abstraction.

Jesse: Mm-hmm. You can’t see the clouds if you’re only looking at the mist.

Peter: Right.

Jorge: And I think that what we’re being invited to do as designers is, I think that a lot of people, and they think design, they think corner radius is of buttons and it’s like, no, folks, we don’t have to worry about that anymore. Or, I mean, not everyone, like I, think that there’s still going to be a role for people who design these beautiful things, but we now have systems that can help apply them at scale in ways that is going to require a lot less human intervention.

And that’s going to free up designers to worry or to focus on higher level things.

Jesse: So the bifurcation still kind of exists within that. The idea of every design system having a robust AI behind it, right, that deeply understands the rules that’s gonna go like, Hey, you know what? Don’t make that corner radius five, make it four. That’ll be better, right?

Like those little guidances I think can really support design as a larger practice.

But then I think the question becomes where does the strategic impact come and where can the technology enhance that higher level of meaningful direction that we started the conversation with, where design can really inform where a product and a business ultimately go.

Peter: I want to follow up on that ’cause, ’cause, you used the word bifurcation and I’ve been doodling on this whiteboard behind me and one of the things I’ve been doodling that’s related to this is the concept of the K curve, which I don’t know if you all are familiar with, but I think it’s becoming a pattern that we’re seeing throughout anything that touches the internet, which is now all of society.

One of the most obvious expressions of the K curve is in wealth inequality, right? The richer, getting richer, the poor, getting poorer, and that’s getting exacerbated, even though, you guys mentioned John Perry Barlow, these technologies were meant to put forth a new society which was going to be utopian. And we’ll all link arms and everything will be great.

And there’s another K curve that I see… is within organizations, and this gets to what you were just talking about, Jesse. And a little bit actually what Jorge was talking about as well earlier, in terms of when we were talking about maturity and you need to meet people where they are and meet their expectations.

And that K curve is most companies building software do it poorly, right? They embrace practices like SAFe, scaled agile framework. They take Scrum and do it wrong. They think they’re being agile and they’re not. And the evidence being, there’s still a lot of crappy software out there.

Maybe it’s better than it was on average than 20 years ago, but not, the sea change we would’ve expected. Going from waterfall to Agile didn’t really drive a ton of material improvements in what was produced. It allowed us to make more. There’s software everywhere, but you could have a good conversation or good argument around, is it better?

My point with calling out how most organizations do it poorly is there are some who do it well. And I think that K Curve is going to apply to these organizations in the application of AI, where those who haven’t yet figured out how to design software aren’t gonna all of a sudden start doing it better thanks to AI…

Jesse: right,

Peter: They’re gonna do more of the bad stuff that they’ve been doing.

And those that have figured out how to do it better are gonna just like… rocket-ship past everybody else.

And I don’t know what those implications are because many of those companies that do it poorly have other things that protect them. So I do a lot of work with banks and insurance services firms, and they have these delightful regulatory moats that’ll enable them to produce mediocrity and thrive. Not even just survive, thrive. ’cause that’s not where the value is located.

But I find myself checking in with any utopian sensibility about how AI is gonna allow us to do better things, if we’re not taking into account the context in which that AI is being deployed and how it’s constraining evidently better things to do today.

Like, why would AI change that? How might AI change it?

Jorge, you have a podcast called Unfinishe. Jesse and I have been playing with Liminal. We don’t know where this is going but I feel like we’re at these edges here of something is coming that’s maybe revolutionary and what is our role, in moving towards whatever is coming?

Jorge: The podcast is called Traction Heroes. Unfinishe is a consulting business that I’ve spun up with Greg Petroff, which we can get into because the name is important. Like we chose that name with intent. And it’s “unfinishe” without the d so it’s literally unfinished.

There’s a quote from Christopher Alexander that often comes to mind, and I’ve pulled it up here so that I can read it verbatim because I think the words are chosen very carefully.

He’s talking about like the role of design, right? And he says, “We are searching for some kind of harmony between two intangibles, a form which we have not yet designed, and the context which we cannot properly describe.”

Jorge: And I really like that because I think that we designers think that the object of our focus is the object. It’s the form, it’s the thing, it’s the screen,

And in reality, what we should be taking in is the fit between that thing and the context it’s looking to address. And we cannot understand that fit if we don’t understand the context and in the context, I include things like the strategic direction.

Y’all had Roger Martin on this podcast, and Roger often talks about the fact that you can’t really separate strategy from execution. I’m not gonna put words in his mouth, but I think he argues that’s not really feasible, right? Like in some ways like strategy is manifest in the execution.

And in executing the outlines of the strategy, at a minimum its impact, the boundaries of where you can act, start becoming clear. It cannot become clear in the abstract. Like you actually have to do things in the world. You have to put the product out and see how people react. Are they buying it? Are they not buying it? Are people failing to discover this particular screen that is essential to the thing?

Those kinds of things you’re only going to be able to answer once the thing is out in the world. And the risk that we run here, this is to your point, Peter, is that we have this new technology that, if approached naively, will lead you to try to apply it to the old ways of being. The ways of being that were applicable before the technology came on the scene.

And you can try to use it to do it the same thing faster or with fewer people, but it might turn out that the thing that you were doing before was only really appropriate in a world where the new technology didn’t exist.

So it’s like you’re now, like, speeding away in the wrong direction, right? So, like, it behooves you to really grok what the technology brings to the table.

And you will only do that by actually doing stuff with it, which is why I’m so adamant in the idea that you have to work with this technology. Like you can’t think about it in the abstract. You have to make things with it. And you have to use it as a material to really understand what it brings to the table so that then you can reconstitute your strategic choices around what new capabilities this thing brings.

Jesse: I am so glad that you brought that up because it, touches on something that came up for me when I was reviewing our last conversation together on this show, and I’m gonna quote you back at yourself.

Jorge: Oh, no!

Jesse: I’m sorry to say. But it’s gonna be good. It’s gonna be good, I promise.

You were talking about working with students and you said, “the analogy that I use is that we are there as something like a strength trainer. You hire a strength trainer to show you good form when doing exercises, and the best trainers are the ones who will know how to do the exercises themselves, who’ve been doing it for a long time, who themselves manifest the practices that they are teaching you.”

So I think there is something to be said in here, coming back to our audience of design leaders you can’t be throwing this technology at everybody and not be immersed in it yourself and not to have your own opinions about what good practice looks like.

Jorge: Yeah. No, absolutely. It’s foundational. The story I often tell is, when I was a student myself in architecture school, we had a class called Materials of Construction. It had two sections. There was one section that was like the theory where you learned all the math around what’s the tensile strength of steel? There’s math behind that.

But then there was a practical component to this, which was, I remember we would drive out to this warehouse and we would don a welding mask and fire up an arc welder and actually learn to weld steel or lay bricks.

And the expectation wasn’t that we would then graduate and become brick layers or welders, but that whenever we drew lines on paper representing walls, we understood what those things represented in the real world, not in theory.

I’ll give you another story. This one was also very influential to my career.

One of the very first books of design that I ever read, it might be the first book of design I ever read is, a book on video game Design by Chris Crawford.

Jesse: Hmm.

Jorge: I think it’s called The Art of Computer Game Design.

I haven’t read it in many years, but this book is from, I think it’s from 1984. It’s the early 1980s. And I bought this book when I was a kid, programming in BASIC, trying to make video games. And I was disappointed because I was expecting that this book would help me, I don’t know, make better sprites. Like I was a, like a pixel- based designer at that point.

But what this book was actually was a conceptual manual of what good design for games is. And one of the points that Crawford made, and I’m gonna have to paraphrase because it’s literally been decades since I last read this, but I remember him talking about the constraints of the systems he was working with.

Keep in mind these are early 1980s, 8-bit computers.

And I remember him talking about understanding that he only had a certain amount of RAM to work with in these computers. And because he was not just a designer, but also a programmer, knowing the computer’s constraints allowed him to make creative choices that he would not have made otherwise.

Concrete example, he was working on this war game and he realized that with a very small memory footprint, he was able to tweak one parameter and allow the game to indicate the passage of time by shifting colors so that it reflected the seasons. And he would argue that a non-creative programmer probably wouldn’t have spotted the opportunity, and a non-technical designer would not have spotted the opportunity either.

Like he was this Venn thing where it’s, I’m a technical person and I’m a creative person. And because I understand the capabilities of the system, I can make better creative decisions.

Jesse: So what are the implications of that insight for AI and digital product design?

Jorge: The most obvious implication is you have to be involved with the technology. Like you have to work with this stuff hands-on and you can’t just read about it. I think that at this point most people who are working in any kind of professional capacity have at a minimum fired up ChatGPT or Claude or one of these chatbots and had the experience of interacting with it. I do think that it’s important to not stop there and really grok what is going on underneath the hood. And I think that once you do, you’re quickly dispelled of any magical thinking…

Jesse: mm.

Jorge: …that might be instigated by this technology.

It is a technology, it’s not a magical entity that all of a sudden is gonna solve all your problems. It’s a technology that you have to work with and it has capabilities, perhaps unparalleled capabilities, but it also has constraints. And you have to understand both.

Jesse: What are the risks? What are the traps that designers and design leaders might need to watch out for as they are engaging with these technologies in design processes?

Jorge: Uh, Wishful thinking,

Jesse: Oh, yay! The problem is solved!

Jorge: Yeah. It’s, “Hey, we got AI now,” you know? We read news about all these companies laying off people because AI, right?

Most recently there was a thing about Block, right? Where they laid off something like 40% of the company, and the messaging, if not necessarily the reality, behind that decision was that we’ve been working with AI and we have all these efficiencies now, right?

I think that you have to be really careful when parsing news like that because there’s a lot of hype. This technology can do a lot of things.

One of the things that it can do is it can be used to excuse a lot of decisions that are being undertaken for other reasons. So don’t think that you’re going to be able to replace humans in the short term with AI, especially for a lot of complex processes.

Like maybe in the long term, a lot of roles will go away. In the near term, we’re just at the very beginning of this. And so I would say avoid buying into the hype that you’re going to be able to replace humans in the near term and still get the same results.

On the flip side of that, avoid the temptation to think that this is a nothingburger. This is a burger.

Peter: You mentioned, Jorge, in your conversations with Harry on the podcast Traction Heroes, and I gather your practice with Greg now, your consulting practice, you’re trying to help the organizations you’re working with be more intelligent about how they’re embracing these tools. And I’m wondering how you are doing that.

What are the points of articulation for intelligence? And just to maybe kick this off, I recently wrote a post for my newsletter that in turn was somewhat inspired by something that an organization designer named Clay Parker Jones, who works for Airbnb, wrote, which is we need to move past role clarity.

It’s not about roles, it’s not about designers and product managers and engineers and really defining those well and then that will solve the problem. We need to move past roles and towards teams. We need to actually be okay that roles are getting blurred, and we need to then figure out how do we just get the right four or five, six people in the room.

And his insight was, provide them clarity. He talks about team clarity over role clarity in order to take advantage of the potential of these new technologies.

I’m wondering if that is the kind of thing that you’re seeing that you’re working on. Are you focused on roles and teams? Are you focused on process? Are you focused on strategy and making sure that the leadership has clarity and is prioritizing appropriately? Like where do you see these points of articulation, at least at this point when it comes to companies or the organizations you’re working with behaving more intelligently.

Jorge: Everything that’s old is new, right? And this is what I was saying earlier in our conversation, that this new technological disruption is an opportunity to revisit first principles and to think about, hey, you know, what is the work really about? If we thought that the work was, in my case, about, if you take the most superficial read of what information architecture is, right, it’s like the work is about structuring website navigation systems, right? Or taxonomies for people to find products in a catalog more easily or what have you.

If you thought that was what the work was about and all of a sudden you have systems that can do that, that forces the question, what is the work ultimately about?

And when you step back and think about we’ve been doing as designers for a long time. It’s about trying to make sense, trying to help move towards addressing some kind of challenge in a skillful way, right?

Obviously this is not the only discipline that does that, but design has this particular abductive way of reasoning where you try to get a sense of what the challenge is about. You explore a bunch of different alternatives, hone in on one, and then put it out there. You put it in contact with reality so that you can start iterating toward good context-form fit in the Alexander sense, right?

And I think that that’s perfectly valid. The risk at stake here, Peter, and the reason why leadership needs help with this right now is precisely what we were talking about earlier, that we’re so distracted by the capabilities of the technology that we can lose sight of the fact that it’s very easy for us to expedite or automate the wrong things.

I’ll tell you what the wrong way to go about this is. The wrong way to go about this is to look at our current processes and then start trying to automate everything without taking a step back and understanding what the ultimate outcome is, right? You want to make sure that you are using the technology appropriately, and that requires understanding the technology, but it also entails understanding how your business or business unit or what have you is creating value.

You know, you need to step back and… it’s like service design, right? And our mutual friend Craig Peters has written about this, this idea that, hey, you start by understanding the flow and you all at Adaptive Path, you published the journey map thing, right?

Like, which was so influential for us. It’s like you’re trying to understand how people move through these changes to come to some outcome.

So you still have to do that. AI is not gonna do it for you. You still have to do that. If you do that now with the understanding that you have these new capabilities, then something interesting can emerge.

I would say the wrong thing to do is to keep doing what we were doing only now faster and more cheaply, which is what you were talking about earlier, Peter. It’s not about start running faster. You might be running in the wrong direction.

This is an opportunity for us. It’s like we’re at an inflection point. We’re being gifted this incredible opportunity to take a step back and say, how are we really helping people here? And how can we do it better now that we have these new things?

Jesse: So I’m curious about how all of this manifests for you in your own practice as a consultant, as an advisor to design teams and to design leaders or just business leaders more broadly. What does this look like in terms of how you actually get things done?

Jorge: It manifests on two levels, and I think that we have to approach it on two levels.

On one level, it’s what we’ve been talking about, which is understanding the technology hands-on so that you can know what it can and cannot do well in the spring of 2026, and I usually don’t do this, I won’t, like, date the podcast, but it’s very important to acknowledge that these technologies are changing very fast, right?

So it’s very important for you to be up to speed with how the technology is currently working so that you can, when advising people at this very high level, how are we creating value thing, so that you have a good grasp on what the technology can and cannot do well, and which approaches work best.

So that’s one level. The other level is the actual doing of the work yourself changes as a result of these technologies.

I, myself, work a lot more these days with Claude and ChatGPT than I do with Figma, right? So…

Jesse: hmm.

Mm-hmm.

Jorge: That’s a transformation in my work.

In some ways, it’s kinda weirdly regressing that I’ve become very chatty and verbose just because the tools that I’m working with are very chatty and verbose. But I also have to become more skillful at describing what I need help with.

Using the tools on myself, maybe this is something we can drop in the notes for the show, but I’ve been doing experiments that I’ve released publicly around things like conceptual mapping. This is a long running experiment for me. It’s like, how can we use these tools to help us make really good concept maps? And I have a tool that I’ve been building over time. The latest release, I packaged it as an agent skill that you can fire up within Claude and you can feed it a text or point it to a webpage, and ask it a framing question and it’ll draw a diagram of the main concepts and how they relate to each other.

So, highest level, how can these tools help us create more value in new ways, not just in the old ways, but at a lower level? How can these tools help me as a practitioner deliver more value?

Because there are things that it can do much faster than I can, and it behooves me to make myself obsolete in those things because if I don’t, someone else will, right?

Jesse: Right. And then you get into all kinds of internal tensions within organizations. I think one of the interesting questions that comes to mind for me is that for design leaders, they’ve got to be looking at their teams and asking themselves, so I’ve assembled this community of visual thinkers, people who can puzzle out problems of pixels and widths and grids and so forth.

But then, now, the challenge is how many of these people are actually also verbal thinkers? How many of these people are actually also people who can use language to describe what they want in a way that they can elicit the correct result from the system that we’re all now being asked to step up to and engage with.

Jorge: And that’s a characteristic of the current state of the technologies, right? And this is where the, like, understanding the constraints comes in. The word language is in the middle of large language model, right? These systems are very oriented to the kind of conceptual thinking that can be best expressed symbolically through language.

And to your point that’s not the only way of thinking, right? There are other ways of thinking. There are some people who are more visual. There are people who are more maybe like kinesthetic, like people who can express themselves through movement, through, I remember at one of the IA Summits seeing people do these workshops on body storming

was

Peter: Bodystorming!

Jesse: Yes. Yeah.

Jorge: Right. Like that kind of thing.

So we are embodied beings and our intelligence, the intelligence that people bring to the table, sure, language is a big part of it, right? It might even be the biggest part of it, but it’s not the only part of it. And I think it’s very important for us to remember that.

This is one of the ways that we can get wrapped around the axle with these technologies. Like we can end up under the delusional impression that because they’re so masterful with language, that means that they are somehow, like, smarter than us, or all powerful or what have you.

It’s like we bring to the interaction a lot more than we give ourselves credit for.

You might flip the equation and say, one of the great lessons for us, one of the big takeaways for us from this transformation we’re going through, it might expose us to the realization that we have capabilities that we weren’t even aware of, just because we had located so much of our value in the stuff that we could language. And now we have systems that can language pretty good, but we are still really good at other things.

Maybe this is an invitation for us to become really good at the intelligences that can’t easily be expressed using words.

Peter: I can, I know I language pretty good.

Jorge: Really good.

Peter: As you were reflecting on it, actually behind me from some client work I’m doing, is Jesse’s elements. Because I was working with a client, relatively small team, about 10 folks that started as a design team.

And so the people on the team were product designers, and then they decided to add what they call design engineers, which can also be thought of as creative technologists and prototypers and that kind of role. And along the bottom on my whiteboard, product designers and design engineers in the middle next to each other.

And then to the right of design engineer, front end developer, right? Because something that they were distinguishing is a design engineer doesn’t do production ready code. That’s where your front end developers are. And then I have to the left of product designer, the first item I put SD.

And that S was purposeful. It could either be, like, a strategic designer or a service designer, and the idea that there’s a spectrum of work happening here, but that the roles are blurring, right? The “who is exactly doing what?”

You have product designers who can prototype and maybe even do production ready code. So what does that mean for the roles? But, getting to the intelligences, I then use Jesse’s elements, right? Strategy at the bottom, then scope, structure, skeleton and surface at the top. Because there’s this question, what does the design team work on?

If we can automate the stuff up top, and there’s a lot of UX that’s not automatable, at least not yet. But to get meta about this, Jesse’s insight required a visual vocabulary, a visual thinking to be able to see this in two dimensions and to recognize the abstraction at the bottom to the concrete at the top. And the left was in the original document. the left was software. The right was hypertext, right?

There was a logic to it that is probably outside the ability of any LLM to have produced a conceptual model with this kind of clarity.

Jesse: This is not where I saw line of thinking going. Okay. Could LLM reproduce the elements of user experience? Is that your question?

Peter: That’s part of where I’m going with this, right? No, but to, Jorge’s point, right? If we are having to identify what is the intelligences that we bring, as I was reflecting on Jesse’s model behind me, I’m like that’s perhaps a direction or an indicator.

Now maybe at some point LLMs are able to do that as well, but that kind of, it’s not just visual thinking.

But to your point, Jorge wordses, and promptses, is only one of many intelligences that we should be considering as we’re thinking about where things are headed.

Jorge: You’re a movie person, Peter. I always remember that scene from Blade Runner where Deckard is sitting in front of the computer display and he’s asking for the system to zoom into a particular part of the photograph. You remember that?

Peter: Oh, of course.

Jorge: I remember, like, even when I first saw that movie a long time ago, I remember thinking, God, that’s a really inefficient user interface, right? Wouldn’t it be faster to pinch and zoom?

But I can totally understand why Ridley Scott would have it there, because you wanna convey like, this is a really advanced society and this is a much better narrative device for what we’re doing with this film, right, if he’s actually talking to it so that we can tell the audience what’s going on with this picture.

As a designer of systems, you need to understand what goal you’re serving, are you serving some kind of narrative goal like Ridley Scott was, or are you actually producing a system that is meant to be usable for humans? In which case, I would argue that’s not a good design, right?

I’m just saying that because we were talking earlier about the things that you can probably be misled by by this technology, and one of them is to assume that the wordy interface is its natural hunting ground, right? Like, just because it is a large language model, the most naive possible approximation of the thing is, like, you slap a chatbot onto the product and it’s, like, now with AI, it’s like new and improved.

Now with AI, that’s a way to do it, but that’s not necessarily the best way to do it. What’s the best way to do it? You have to really grok what the product is trying to do, and you have to grok what the technology brings to the table, what we were talking about earlier.

Peter: You need to have a pretty firm sense of what you want to accomplish.

Jorge: Right. Well, exactly. This is the point…

Peter: People approach these tools and then are like, now what? I don’t know I want to do.

Jorge: Are you trying to help make this experience easier for the user so that they can check out faster? Or are you trying to bump the share price by saying “now with AI”?

Those are different goals and it might be that there might be a way to, like, synchronize them so that hey, we’ve made it better for people and we’ve communicated to the market effectively that we are now using AI or what have you.

But you have to be clear on what goal you’re serving, before you start like investing resources in moving in that direction.

Jesse: Even if AI resources are the cheapest resources, and most plentiful available, right?

Jorge: I would argue that they’re not, because if you’re implementing them in a way that leads you down the wrong path, that may end up being costlier than doing it the old fashioned way.

To Peter’s point, it’s like you can start running very fast in the wrong direction.

Jesse: Yeah. And I think it’s interesting the ways in which people invest in the AI a kind of sense of a source of universal truth. An all seeing Oracle to be consulted about the correct way to do anything at all.

That, I think people don’t build into their processes enough of a sense of teaching the robot what good actually looks like, and teaching it the constraints of your business problem, the constraints of your design problem, the constraints of the problem space that you’re facing more broadly.

I have talked about this in the past, as fundamentally being a skill set of iterative problem framing, because you’re gonna frame the problem. The robot’s gonna get it wrong. You’re gonna reframe it, it’s gonna get it wrong again. But you’re going to refine that down to a problem frame that the robot can actually understand.

Jorge: This might be a good place to like start bringing this together.

Both of you have talked for a long time about the need for a language of critique for the things that we do. And I think that’s becoming ever more pressing now that we are forced to… well, forced. Let’s say we are invited to ask these languaging systems how to work with them and how to create effective experiences.

Our mutual friend Peter Van Dijck has been teaching designers about AI evals, right? That’s a big phrase in the AI space, evals. It’s like, what do you mean by evals? It’s like, basically is the outcome matching up to your expectations, right?

And I think that we need to circle back to that now, more pressingly than ever because we are on the verge, if not past the verge of creating systems that will do it at scale in ways that humans can’t.

Giddy up.

Peter: Maybe to put a button on it, something I’ve been thinking a lot about, and I hadn’t known this was something that van Dijck was working on, but, a year ago when Figma did their first design and AI report, they said some teams are going faster, but no team is going better.

Like, they’re producing mediocrity faster. And it surprised them that the quality wasn’t somehow improving, ’cause thought they would also be getting, because of the ability to iterate or whatever.

And this gets back to the intelligence conversation and the clarity conversation. For me, I think the quality’s not improving because there was never a standard of quality to begin with.

So there was no, there was nothing to calibrate against. There was no measure to understand what good looked like beforehand.

Jesse: Only executive taste, right.

Peter: Right. And so we rely on discernment and taste, but those are personal. They’re preferential. They’re not global…

Jesse: Yeah. They’re informed by individual experience. Yeah.

Peter: Yeah.

Jorge: Peter you have the elements sketch behind you. I would argue each level in the stack needs evals, right? You need to understand what good means for strategy and that’s going to be different than what good means for surface, right? And it’s not evenly distributed. We have a better sense for some of the stacks than others.

And now that we are working with these systems that are so good at following our requests, right? We have to get really precise at describing what we want at each of those levels. And maybe that’s one of the things that we humans can do better.

Now, again, going back to this higher order of abstraction is, like, we can see the big picture. We can stand back and say, yes, the things that we are doing at the surface level are supporting what we want to accomplish strategically, right?

Jesse: You won’t get any, any disagreement from me.

Jorge, thank you so much for being on the program. It’s been fantastic to have you back.

Jorge: It’s always a treat to talk with you all. I’m always, I always leave hyped up and energized, so…

Peter: I was about to say we, we could easily go for another hour, if not more. Hopefully the folks listening to this are okay that we didn’t solve anything and instead that we just fired their neurons and hopefully encouraged their continued exploration in this space.

Jorge: Can I riff on that real quick? I think that if you come out of any of these conversations feeling like you’ve got the answer, you’re probably wrong. The technology is changing too fast. Like that’s why we called it unfinished, because it is.

Jesse: Yeah, that’s exactly right.

Peter: If you think, you know,

Jesse: You’re wrong.

Peter: You’re wrong.

If you are uncomfortable, you are doing it right.

Jesse: Jorge, thank you so much.

If people wanna follow up with you and your ideas on the internet, how can they do that?

Jorge: The easiest way is my personal webspace. It’s jarango.com, and you’ll find links there to all the places you know, from LinkedIn to Unfinished to the Traction Heroes Podcast.

Jesse: Fantastic. Thank you so much for being with us, Jorge.

Jorge: Thank you for having me. It’s such a treat, and let’s not wait another five years to do it again.

Jesse: All right.

Jorge: Next time it will be only LLMS among themselves.

Jesse: There we go. We’ll dispatch our agents. Thank you.

Speaker 3: Hey all, it’s Peter again. Don’t forget about the Finding Our Way Live Event on April 3rd. Find more on LinkedIn on the Finding Our Way page and the Intentional Design Leadership Circle. The six week cohort. Jesse and I are organizing starting April 15th. Find out more about that at finding our Way design slash circle.

I.

Jesse: For more Finding Our Way, visit findingourway.design for past episodes and transcripts, or follow the show on LinkedIn. Visit petermerholz.com to find Peter’s newsletter, The Merholz Agenda, as well as Design Org Dimensions featuring his latest thinking and the actual tools he uses with clients.

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