Denise: Feeling so full of what I was capable of, and so in love with what I was capable of that I thought, well, what else can I do? If I can accomplish this major thing, what other major things can I accomplish and can I give to the world of myself? And when I had that experience, I was like, that’s what I want to help people with.

I want to help people feel like this.

Peter:  I’m Peter Merholz.

Jesse: And I’m Jesse James Garrett,

Together: And we’re Finding our Way…

Peter: …navigating the opportunities and challenges of design and design leadership.

 Jesse: On today’s show, author and consultant, Denise Jacobs joins us to talk about maintaining a creative culture, how leaders can keep the creative spark alive in their own work, fighting imposter syndrome, banishing the inner critic, and a lot more.

Peter: I have a question for you, Jesse.

Jesse: Yes?

Peter: Why did you invite Denise on our podcast?

Denise: He said, “I have questions.”

Jesse: I do have questions. I have questions for Denise. So, Denise Jacobs… actually, you’re going to do a better job of introducing yourself than I am. Denise Jacobs, who are you and what…

Denise: Oh, you think so?

Jesse: Do you do? I do.

Why don’t you describe the areas that you work in.

Denise: So my springboard area of expertise is creativity because I’ve been doing a lot of work on creativity since 2011 and, doing keynotes and workshops and whatnot on it, but then came out with my book, Banish Your Inner Critic in 2017, which was all around creativity.

But the interesting thing is how some piece of work starts to put you into a new direction. And so now I’m focusing a lot, not just on creativity specifically, but more around how people can do better work through silencing that voice of self-doubt, so what you are able to accomplish and what you’re able to do, whether you’re at what I call the producer level, if you’re a UX designer or a developer, but then when you get kind of more to the managerial level, or even to the leadership level, how can you do what you do better through acknowledging that inner critic and having tools to be able to combat it so that you can actually show up more powerfully.

Jesse: One thing that I love about the book, that you touched on a bit here, is that it does go broader than simply issues of creativity.

Denise: Absolutely.

Jesse: Although it definitely is through the lens of being a creative professional and has a lot to say about the specific tactics for creative professionals, the principles there are really, in a lot of ways, about self-actualization.

Denise: That’s totally it. Definitely, I feel like the true goal of my work, and actually the reason I even started working around creativity in the first place, was to get to that place of self-actualization, because I had had this experience where I had this amazing creative flow state, and I felt so empowered and I felt so like, full of myself, in the respect of being full, like not needing anything else, you know, not needing the external validation, not needing somebody else to tell me it was okay, feeling so full of what I was capable of, and so in love with what I was capable of that I thought, “Well, what else can I do? If I can accomplish this major thing. What other major things can I accomplish? And can I give to the world of myself.”

And when I had that experience, I was like, that’s what I want to help people with. I want to help people feel like this. And at the time, because what I needed was to reconcile myself and to come to terms and embrace and acknowledge and recognize my own creativity, the answer for me was creativity. But now that I’m along this path of a breadcrumb trail that led me to inner critic work it’s just like, “Oh, this applies to so much more than creativity.” And it affects people so profoundly, it’s such a universal affliction.

Jesse: So our audience is design leaders, and a lot of these folks find themselves awarded responsibility in their organizations, because they were really good at the creative part of their job, they found a way to create for themselves that creative flow and that energization that you’re talking about.

And then people looked at them said, “Wow, you’re doing so great at this. We should give you more responsibility so that you are now doing less of that. And you’re doing these other things instead.”

Denise: ”You’re doing so great at this, that we’re going to make you do something completely different, that you have no idea how to do. And of course you’ll naturally be great at that because….” What?

Jesse: People who were previously very confident in their jobs, find themselves in these new roles, and find that confidence has been taken out from underneath them because they’ve been cut off from the creative practices that connected them to that sense of power that you’re talking about.

Denise: Absolutely.

Jesse: So I wonder what thoughts you have on the challenges of keeping creativity alive in your work, when your work is no longer strictly creative work per se.

Denise: Okay. So I actually have two things that I want to say. I’ll answer that question in a moment, but before I go into that, what I want to say is, that whole process that you just described is one of the key times that the inner critic becomes so loud for people, it becomes so prominent, and it’s become so in their face and forward. And that is exactly the work that I am focusing on now is helping people with their career confidence. Because it is in that transition that all of these mechanisms go into play that trigger the inner critic. Having said that, the interesting thing is that the same tools and the same practices that you use to silence your inner critic, to unblock creativity, are the same constellation of tools that you can use to counter that feeling. And in doing so get back to your creativity.

Jesse: So, I’m an independent leadership coach now and one thing that I say to people is that leadership is a design problem.

Denise: Preach it.

Jesse: And, you’re working with different materials and often the materials that you’re working with are your relationships with other people. And it’s in relationships with other people often that this inner critic stuff gets kicked up for people.

Denise: I actually just finished reading a great book that’s going to be coming out by a friend of mine his name is Mark Pitman. And his book is called The Surprising Gift of Doubt. And it is how uncertainty can help you become an exceptional leader.

And one of the things that he talks about is the other problem with moving from a role where you were doing something really well, and it was creative and everything, to being a leader, is that you think that there’s a certain way to be a leader. And there’s not a lot of support, I think, about giving people the space to discover how they lead, and have the exploration and the journey that people have to go on to be able to discover all those things about what works for them.

Like, if you’re not extroverted, then being a loud, extroverted leader is not going to work for you. And then you’re going to feel even more out of sorts, you’re going to have even more of an inner critic dogging you, et cetera. And so, it is this design problem. And then it’s also this journey of discovery, which a design problem basically is. Solving a design problem is a journey of discovery.

But very few people contextualize it that way.

Peter: Creativity is one of those funny words.

Denise: It is a funny word.

Peter: Just to make sure that we have a common understanding of what you mean by creativity: How do you define it? How should we be thinking of creativity?

Denise: My main working definition of creativity is bringing something new into being.

Peter: I think so often creativity is associated with things like the arts or writing and those types of practices, which are clearly creative practices. What is the connection you make, if any, between those expressive forms of creativity and the kind of creativity you’re encouraging through career confidence, through designing your own future?

Denise: Because my background, as a front-end developer and somebody who used to teach HTML and CSS and work with software engineers, I’m always very careful to, very point blank, say that art and creativity are not the same thing. Making art is not the same as being creative. You can be creative in anything. You can be creative as a social organizer. You can be creative as a scientist. You could be creative as a CEO.

Creativity basically is problem solving, whatever this problem is, however it needs to be solved. If you come up with a solution to a problem, you’re exercising creativity.

So, when people are trying to cultivate their confidence, trying to step into a new position, expanding themselves, getting to self-actualization, all the things that we’ve been talking about previously, they are using creativity because, first of all, they are bringing something new into being, and second of all, they are problem-solving.

You’ve got an issue. “I’m where I am now. I don’t want to be here anymore. I want to be in a different place. What do I need to do?” And then you go along the process of figuring out what you need to do and taking the steps for it. I truly believe that that is exercising creativity as well.

Peter: Thinking about working with design leaders, I don’t have a formal coaching practice, but I work with design teams and design leaders as well.

If I want to be encouraging creativity appropriately, for both them as individuals and maybe a team, what does that look like? How do we know that they are hitting enough creative cylinders? How do I look at something and go, That is appropriately creative!

Denise: That is actually an outstanding question. And I will give you an answer that probably is not substantive for you. It’s not based on metrics or anything like that, because, I feel like first of all, when you start to get into, How creative is it on the spectrum? Is it zero? Does it go to 11? Then you start getting into this judgment about creativity, and then that will set up a whole other thing that’ll trigger your inner critic. “I’m not creative enough.”

As a matter of fact, one of ways that I got to some of these forms of the inner critic that I talk about in the book, are from this exercise that I’ve done at conferences, workshops, where one of the things that people said very frequently is, “I’m not creative enough.”

What does that even mean?

If you’re creative at all, like you’re winning, right? If you’re doing anything you’re winning. So I feel like then trying to quantify it like that is dangerous and that it needs to be more of a qualitative analysis where it is, How do you feel when you’re in this process? Does it feel good or does it not feel good?

I would say that, because it feels good, then that means that you’re being quote, more creative. And I think when you’re working with teams at the end of the day, what they create is important.

But the experience of working together and everything, is going to have more longevity and more importance to the functioning of the team than the actual thing that they produced. And the dynamic within the team will also affect the quality of what they produce. So if they’re having a good experience, if they’re connecting with each other, that will be something that they can all feel and experience. And when that’s not there, they will also be able to recognize its absence.

Peter:  Calling me out on my desire to reduce or, quantize things that aren’t quantized… There’s a history of that Jesse’s and my conversations. I’ve done the same with the concept of trust, trust is one of those things that the moment you try to start defining it, you kind of lose the plot, right there.

And I think that’s what you’re saying about creativity. If you try to put it in a box that you can look at and study it, then you’ve kind of lost the point of that energy, that flow, that forces that the creativity is providing.

Jesse: It’s almost by definition, if you can capture it in a box, it’s not the thing you’re looking for.

Denise: Right. And it’s also like, how do you know if you’re really in love? Because it feels good.

Peter: No, no, no, no. You write long lists of pros and cons. Isn’t that it? And then you…

Denise: You rate it on a scale of one to ten…

Jesse: You weigh them all and you build your spreadsheet.

Denise: Exactly. Does it feel good? If it feels good, then you’re in good shape. If it doesn’t, you know, you gotta leave.

Peter: Okay. I know Jesse’s probably itching, but I got to follow this one up. Because one of the challenges that design leaders, design teams face within organizations is working often with peers–engineers, product managers, marketing folks–who are highly quantified. They want everything to be metric-ized, and they want everything to be A/B tested or somehow proven.

And I’m wondering how you’ve been successful in bringing this force and energy into organizations that might not have been ready for it. Because their mindset had been so analytical, mechanistic. What have you done to make that kind of change?

Denise: The interesting thing is, if I’m in an organization, it’s because they want something different than that, what they’re looking for is that ineffable quality or thing that they can’t put their finger on, or quantify or anything.

They’re looking for the energy and the spark of creativity and flow and connection that they weren’t able to achieve through the more analytical means.

Jesse: A lot of this comes back to creating and maintaining a culture of creativity for the design organization, and then being able to hold that boundary, and shelter that creative culture from whatever the larger culture is that people find themselves in.

Denise: Yeah. Or to even, try to get the leaders on board so that they are instrumental allies and even champions of this culture.

Jesse: Right.

I think one of the challenges in creating that culture of creativity is having a culture of constructive critique rather than criticism.

It’s something that a lot of design leaders find a hard time striking the right balance, creating enough support for creative exploration on their teams, so people can try new ideas and play around at the edges, while also being able to provide constructive feedback to teams that channels that work in a way that brings it to fruition.

And in a lot of cases, I feel like our inner critics take their cues from the outer critics, the people around us and the culture of critique versus criticism in how creative work is handled.

What are the tactics, for encouraging that balance?

Denise: Yeah, I think our inner critics really are responding to outer critics, and our inner critics literally developed because of outer critics. Our inner critics developed as a psychological construct that came as a protective mechanism to help us deal with and potentially even try to subvert having any outside criticism come in. You know, you get those early on and you’re like, well, I don’t even know what I did, but I’m going to be super hypervigilant now to try to prevent something like that crap ever happening again.

Very, very few people have ever been critiqued properly. Have never been given feedback in a way that is actually supportive or good or positive. And then we learn that, and then we think that’s how you do it.

I actually had a manager at Microsoft, where… I go into my one-on-ones with my manager and he was like, “You were in that meeting, that should have like triggered your localization ear.”

And I was like, “I literally don’t know what I’m supposed to be listening for. Can you tell me what it is I need to listen for?” And he was like, “You know, Microsoft is a sink or swim environment. So either you’re gonna sink or you’re gonna swim.” I was like, “Not helpful, manager.”

When you go in to get feedback, structure the feedback as much as you can, so that you get what you need, and through doing that, you essentially train the person who’s giving you feedback, how to give you feedback.

Like you’re gathering information for a friend and then you’re trying to find specific information as much as you can. Asking for this information in a certain way, this is not about their character or whether they’re good enough. I’m trying to give them information so that they can do their job better.

Jesse: I really like this idea. I think it’s interesting from a couple of angles. One is that in critique situations, the person whose work is being critiqued, often adopts this very passive powerless stance in the meeting. And what you’re advocating is really for them to act like it’s your meeting, not their meeting, and take control of the process.

And I think broadly for design leaders, as they are often engaging in processes that they have limited influence over, wherever you can find ways to take back control of your processes from people who don’t understand your needs, those are places where you can expand your leadership, and those are leverage points where you can get farther.

Peter: Something I think I’m realizing as you talk about silencing that inner critic, if you can separate your sense of self-worth and your identity from the work you’re producing, you will, frankly, no longer feel the criticism because it’s not about you.

So much of the challenge with this fear of criticism is it feels like it’s about you as a person, an entity, your identity, your worth in the world. And helping people create a bit of healthy distance between them and what they produce, and make it about that thing that you’re producing, and anyone can criticize that all they want—is that thing achieving the goal, is that thing, based on whatever rubric, working—but it’s not about, “Am I a better or worse person because I made that thing,” and one of the challenges I’ve had throughout my career is people get so caught up in their identity with respect to their work. It becomes a reflection of themselves.

Denise: That’s been one of my own personal struggles, when I create something it’s like, “This is my baby. This is a piece of me,” and getting to the place where there is the ability to practice some of that distance.

Jesse: I want to talk a little bit about the inner critic because it can be a bit of a slippery concept and it certainly can look very different for different people.

Tell us a little bit about some of the different forms that this shapeshifter, the inner critic, might take, that people ought to be watching out for.

Denise: I feel like the inner critic does show up in a lot of different ways. And a lot of times people will talk about imposter syndrome as its own thing. I personally believe that imposter syndrome is a form of the inner critic. Perfectionism is a form of the inner critic. Being highly self-critical is a form of the inner critic.

Being afraid of being judged, comparing yourself to other people. Fear of failure and success can be a form of the inner critic, and procrastination/self-sabotage can also be a form of the inner critic.

And those fears that we have, those fears of not being enough, or those fears of being found out, are these kind of deep fears of who we are afraid that we are, they kind of get in the way. And they keep us from being who we can be.

Jesse: For leaders, I think there is this additional challenge of supporting their people in contending with their own inner critics. And what are some of the things that a design leader might want to watch out for among the folks on their team that indicate that somebody might be struggling with this and it might require the leader to step in and provide some support.

Denise: A lot of times, I feel like in creative, collaborative environments, what happens is people tone themselves down. People silence themselves. There was a great article on 99U by Matt May, that refers to “ideacide.” And I love that term, the concept that you’re killing your ideas before they have the opportunity to come out and really see the light of day, and sprout and blossom. And maybe they are kind of non-starters, but you never know until you actually give them an opportunity to come out.

And so often people will be in meetings… Talk to them one-on-one and they’re just like, “Well, I was thinking this,” and you’re like, “Oh my God, that’s a great idea.” And then there’s the meeting where the perfect opportunity for the person to share that idea, and they don’t say anything and you’re practically kicking them underneath the table.

Like, “Say the thing that we’ve talked about…!” “No, no, I don’t think, no.” And I feel like that happens so often with a lot of people that it’s become second nature. And what I think would be helpful for managers and people leaders is to recognize where that’s happening.

And the other thing too, especially in light of Black Lives Matters movement and a lot of what’s going on, people of color, women, anybody in a disenfranchised group, is going to have a stronger inner critic because society literally makes them have a stronger inner critic. And so then that self-doubt is going to be even stronger. And so, if you’ve got women on your team, if you’ve got women of color on your team, if you’ve got people in the LGBTQ community, they may not have that strong sense of self. They’re not going to share their ideas.

And, it’s also very common for white men, or men, to talk over these people, to discount their ideas to start. So this is kind of a hot mess. I think that’s the technical term.

Jesse: Well, definitely in my own coaching work, I’ve worked with number of women, and the challenges that they face, in particular of feeling like they have to adopt masculine communication styles in order to be heard, it really ends up driving them into this deep place of self-doubt about their own instincts. They stop trusting themselves.

 I want to get your take on introverts though, because this is a topic that’s come up previously on the show. And my hunch is that many, maybe most, people who self-identify as introverts are actually hostages of their inner critics, who have developed a robust case of Stockholm Syndrome and have fully internalized that sense of being trapped into their own identity.

Denise: Hmm. So, I found this tweet not too long ago that was pretty profound and insightful. And it was more about imposter syndrome, but I can see this having a direct correlation with introversion as well.

And it said, “I wonder if what’s called imposter syndrome is just a way to rationalize how women and people of color have been treated all of this time.”

Oh my God. Like, just amazing, right? And I feel like that could totally be true, too, of introverts. That there is this thing that, you’ve been talked over so much.

So here’s one that says, “Maybe you don’t have imposter syndrome. Maybe you’ve been treated like an imposter your entire career.” And then here’s the one that I was looking for. “Sometimes I wonder if imposter syndrome, originating from the 1978 concept imposter phenomenon, is just another example of making racism and sexism and professional spaces appear as a psychological myth rather than a structural reality of how people get poorly treated.”

Jesse: That’s great.

Denise: It’s amazing, right?

Jesse: Whose words are those?

Denise: Tamara K. Nopper.

Jesse: Alright, thank you, Tamara.

Denise: Again, it’s like you said, this internalization of, “I think differently, I like to think before I talk, not think as I’m talking, and I actually want to find out what’s going on before I weigh in on something.” And then it’s like, “Oh, that makes me an introvert.”

Yeah, or you just haven’t had the setup and the structure for you to be able to be.

Introversion is definitely a spectrum. I like to say that I’m like 60, 40, or 40, 60, depending on the day. I would say that I’m an ambivert. But, you know, when I’m really tired and everything, everybody out of the pool. And I just want like a cup of tea and a book and like a cat on my lap, like out, I don’t want to talk to anybody.

I’ll turn the phone off. I’m like, “That’s it, it’s over, cancel Christmas.” So, what ends up happening is that if people were in an environments where they felt more comfortable, and they were given the space, that they would probably be super-talkative. They would probably be more like a typical extrovert, but they’re not given the space for it.

And extroverts take up a lot of space.

Peter: I’m reading the book Caste, that just came out, by Isabel Wilkerson. She hasn’t really addressed work contexts. It’s much more societal.

However enlightened and sensitive we’re trying to be even within our offices, and as we’re embracing matters of diversity and inclusion as companies, and as individuals, I mean, Jesse and I, as white men, have talked about this on this show, how we’re trying to practice being better, more supportive, in these regards.

In her book, she has this story of going to a conference in India, I believe, about caste, which is essentially a critical discussion. These are folks who are trying to do away with or understand it so as to repair their society. And afterwards, she approaches someone and asks them, “Are you in what would be considered the dominant caste?” and the woman that she says this to is aghast, because she’d been trying to be as woke and as sensitive to her standing as she could. And Isabel’s like, “Yeah, I could tell by the way you interacted with other people and they interacted with you that you were in a dominant caste and those other people were in a subordinate caste,” even though everyone was trying to be explicitly not caste based in this structure.

And it just shows how deep it goes. And one can only imagine this is true in the workplaces we are part of, however, again, sensitive and D&I-oriented we’re trying to be.

What approaches or strategies or tactics can be taken to allow as many voices in a room to be heard and, to be able to contribute?

Denise: Another great quote that I saw, which I spoke about it in a conference that I spoke at, the Enterprise Experience conference, and it said something to the degree of, “Racism won’t end until white people stop looking at as an issue that they need to be sympathetic towards, and look at it as something that they need to solve.” And I was like, yes, exactly. White supremacy won’t die until white people see it as a white issue they need to solve rather than a black issue they need to empathize with.

And I think that’s really true. Castes, racism, sexism, everything, it can’t be solved by the people who are the recipients of it. Or who were on the low end of it. It has to be solved by the people who put it in place.

And I think the more people see these issues as, “Oh, this is something I have to do something about,” rather than, “Oh, I feel so bad.” You know, like, “Oh, I feel so bad about that. It’s so wrong that you have to experience that.” It’s like, “Yeah, it’s really wrong that you benefit from it all the time. That’s really sad too.” And that it becomes more like everybody working together to try to address this issue, rather than “good luck with that,” right? All of the awareness and everything has been so long overdue, but as a black woman,  has also been exhausting because it’s just dredged up so much.

But, you know, at least, now if I say something, it’s not going to be people being like, “That’s not an issue. That’s not a problem. I don’t— Why are you so upset? Why are you so upset? Why are you so angry?” I’m, like, “I’m angry because this is some bullshit. That’s why I’m angry.”

I’m angry because this is ridiculous and it should have gone away. It should have been, you know, I grew up in the seventies, like we were under a false sense of security that it was just going to keep getting better and better and better. And then like just crazy things just keep popping off.

We really need to do this collectively. Like you think you benefit from this, but you don’t. All the things that have been an outcome of racism and white supremacy, okay, so great, you are able to buy a house more easily and all this stuff, but then you end up going and being in suburbs that are completely, homogenized and then you don’t get the culture. You think you’re safe, but you don’t feel safe when you go into other neighborhoods.

But what if you could just be safe everywhere? What if you could just have everybody everywhere all the time didn’t have to be afraid? Like, I kinda think everybody would benefit from that. Other people don’t feel the same way, but, I’m biased.

Jesse: I think we all are. Yeah.

Denise, thank you so much for being with us. It’s been a wonderful conversation.

Do you have anything to plug? Where can people find you on the internet?

Denise: Yes, the interwebs. So you can find me at denisejacobs.com is my website. On Twitter and Instagram I’m @denisejacobs. On Facebook, you can follow me at denisejacobsdotcom all written out. On LinkedIn, I’m Denise R. Jacobs.

And actually, I am going to be launching an online course on career confidence. It’s called Amplify You: Cultivating Career Competence. And so you can go to http://amplify-u.com and check that out. And then finally, I have several courses on LinkedIn Learning, and so you can go and look for me as an instructor on LinkedIn Learning and go and check out my Banish Your Inner Critic to Unleash Creativity course, the Creative Collaboration course, the Creativity for All: Hacking Creative Brain course. And then coming out, I think in December, is going to be the Business Case for Creativity to help leaders champion their cause for creating a creative culture in their organizations.

Peter: Hmm. And there’s the book.

Denise: Oh, right. And then there’s my book, Banish Your Inner Critic, which you can buy on amazon.com. I mean, you can also probably roll into most Barnes and Nobles and find it right when you enter the store in the bargain book section. I know, but still it’s in hardback and it’s wonderful. So you can get at a Barnes and Noble. If it’s not there, you can just ask for them to order it or you can order it on Amazon.

Jesse: Wonderful. Thank you, Denise. This has been great.

Jesse: And with that, this has been episode 21 of Finding Our Way. You can find the previous 20 episodes as well as this one, as well as probably some future episodes, too, that I don’t even know about on our website at http://findingourway.design/, where you’ll find audio and transcripts for every episode. Plus, there’s a way to send us feedback on our website.

Please send us feedback. We love your feedback. You can use our website or you can just write to us on Twitter. I’m @jjg he’s @peterme, or you can find us on LinkedIn under our real names as well. We’ll see you next time.

Erika: Most of what operates under the label of “design” right now is styling business models. It’s not actually design because you’re not making meaningful choices. The choices have been made. They’re outside your purview and designers are chasing after it, coloring in the boxes.

Peter: I’m Peter Merholz.

Jesse: And I’m Jesse James Garrett,

Together: And we’re Finding Our Way…

Peter: …navigating the opportunities and challenges of design and design leadership.

Jesse: On today’s show, veteran design consultant Erika Hall of Mule Design Studio, author of the books Conversational Design, and Just Enough Research joins us to talk about whether designers are truly ready for that coveted seat at the table, how to build those crucial cross-functional relationships, and the relationship between design and capitalism.

Jesse: So let’s jump in.

Peter: You have recently said something that I want to hear more from you and hear Jesse’s take on what you’re saying. I believe the phrase is, “The business model is the new grid.”  What does that mean?

Jesse: Well, that sounds great because I have no idea what that means.

Erika: Oh, fantastic. So what that means is, the important design now is interactive digital design, however you want to construe that. And we’re still drawing from the graphic design models. We still think of like, What’s the platonic ideal of this? It’s like graphic design, but now it’s in a web page or on a screen or something.

And, I think the whole field of design is working from this horseless carriage way of thinking about it. Yeah. Because the grid is not what constrains your work. It’s the underlying exchange of value. And I think when designers don’t realize this, they do all this talking about being human-centered and empathy, myah-myah-myah-myah-myah, and then they’re shocked, they’re shocked when their work is being used to exploit people or extract value or do some rent-seeking bullshit, like all these delivery companies that are vampires on local restaurants, and designers don’t have any tools to confront this situation because they are borrowing the practices of the kind of work that’s irrelevant.

And so if you think about fundamentally, What does your design snap to? It snaps to the business model.

And there’s no overcoming that. There’s no amount of empathizing with customers that will change that because ultimately your work will be deformed to, perverted to, constrained to that underlying exchange.

Peter: All right. You know, we talk about design operating within constraints. The business model is the singular constraint through which everything gets molded, regardless of…

Erika: Yeah. And the business model can be designed. And I think this is the most important work for designers, ‘cause designing business models is within the skill set of any good, like, designer. To really understand what everybody needs, how to reconcile and balance those needs, and how to create a system that creates a flow of value among all the different parties.

It is not intellectually difficult, like getting an MBA is not an exercise in stretching your intellect. So, I think the mechanics of business a designer can understand, but when they think about business, they think, “Oh, I’ve got to prove the ROI of my work. I have to think about KPIs.” And they think about like, “How do I fit my sketches into something where the people in the C-suite will care about me?”

As opposed to, “Wait a second. The people in the C-suite are fucking everything up. Chasing this weird exploiting growth engine, but I, as a designer could redesign the system and come up with something where you create a product, a service, an entity, whatever that actually adds value to the system and doesn’t extract it.”

And people are happy to pay for things. Like, people pay for stuff all the time. People pay for things that are valuable, but price is a signal has been completely obliterated by the availability of capital to subsidize services and products and make them free. Like nobody knows what, say, an Uber ride costs, what a taxi ride should cost, because the pricing signal has been completely camouflaged by subsidies from investors. So that’s what I mean by the business model being the grid.

Jesse: I’m hearing a couple of things in that statement. One is that designers need to understand business factors, the business variables, the business constraints that influence the success of their design work. And then secondarily, there’s an opportunity to do that design work or to do some system level work that resembles design at the level of the business model separate from what anybody might have considered to be their job as a designer in the past.

Erika: Yes. And I think most of what operates under the label of “design” right now is styling business models. It’s not actually design because you’re not making meaningful choices. The choices have been made. They’re outside your purview and designers are chasing after it coloring in the boxes.

Peter: I wholeheartedly agree. The challenge that I perceive, working with designers and design leaders, is how they get into that earlier framing conversation. Often design is not seen as a contributor to strategy or business direction.  Even when you have very smart, strategic people in design, they’re often painting within boxes that someone else has established.

They might be doing so very intelligently and very systemically, but there’s still some barrier between wherever design lives and wherever those conversations are happening. What have you seen in terms of how design can, I don’t know, storm those gates get beyond the castle wall and influence that? What is the move to start having the conversations that you’re encouraging them to have?

Erika: Well, it’s not easy to do that. I’m not saying like all of a sudden it’s like, “Oh, I just realized. Hey CEO. I just realized that if we don’t fix the business model, everything else is jacked and my work is pointless.” That’s not going to happen. So I think it is going to be very similar to, you might recall, the early days of UX, and how there were some prominent UX consultancies that shifted the conversation.

I think the same thing has to happen because it doesn’t make sense to have a strategic design agency in the same way anymore in terms of making artifacts, because that work has all been pulled in house. And that’s the other part of the conversation people haven’t been having, which is, pulling design in house fundamentally changes design.

It changes the practice. You can assess your influence as a designer by thinking about what the limits of your freedom to ask questions are. Like, if you can walk in and say, “Why are we doing this as a business?” you have a lot of influence.

If you’re not allowed to raise questions, then your design work is relatively more shallow. Jesse named two things. So the third thing that’s going on is that design being pulled in house has changed design because they’re no longer questioning from the outside.

So to answer your question, Peter, what has to happen is the new design consultancies are actually more like management consultancies, but without the baggage of a McKinsey and without the willingness to solve any problem. So I think it’s probably similar to the work you’re doing now, where some designers who are very, say, seasoned, do lead by modeling a new kind of consulting and defining a new practice area because people inside cannot set the terms of the conversation, but people outside can push on that and articulate this and do some consciousness-raising. So I think just like UX started as something from the outside that pushed business, this again is going to be a new kind of consulting agency, and a new kind of thinking and talking and discourse that’s going to push on organizations and push on people within those organizations, because you can’t change it from the inside.

And it’s particularly challenging because a lot of people are very successful doing that thing. So where’s the incentive for them to change?

Peter: So are you stating, categorically, that a VP of design within some enterprise cannot make the kind of business model change that you’re articulating. and that instead that VP might be able to help bring in some type of external consultant, recognizing a problem is occurring and say, “Hey, why don’t we approach it from this way? Here’s a group that can help us,” but that VP themselves, you’re in the system, you just can’t unmake it.

Erika: Yeah, that’s the case. There might be exceptions. The only exception I could see is if the organization were in crisis. We’ve seen this in our own work when we’ve been brought in from the outside and then something failing about the business provides an opportunity for them to change.

But if the business is functioning, according to the metrics it set for itself, you can’t change that, because what a lot of organizations are doing is shareholder-centered design. And if the shareholders are happy, that’s the only metric that matters in a business, ultimately. And I think these are maybe be like hard truths, and I’m not saying you can’t do anything good or valuable.

But I’m saying that you’re work as a designer is bounded and constrained by this. And you cannot transcend that. If you’re working for a good company with a good business model and you’re contributing into that, that’s great. But if you’re not, then I don’t care how much you go out there, and learn about people and empathize with people. That work is ultimately going to be used in support of that business model. And there’s nothing you can do about that from the inside.

Jesse: I think that whether or not people see themselves as being capable of taking on that role has a lot to do with their roots as designers and the values that they internalized about value, about the value of their work, about the value of design. I have my own biases here because I don’t have a formal design education, but I’ve worked with many people who do, and I feel I’ve seen certain patterns in how they think about their work.

I feel like I meet a lot of people who came out of formal design education with the idea that their job was to be the conduit for universal principles of design truth through their work. And their job was to go to school, absorb all these principles so fully that they could apply them in any context that they found themselves in.

And their job was to show up and be the expert on grids and typography and all of those kinds of things. And so they never really thought of themselves as designers of systems or systems thinkers. But then if you do think of yourself in that way, then the question becomes, well, What are the boundaries of your practice? If my job is to be a systems thinker, trying to humanize the systems of the world, what’s off limits for me then? And what is within the bounds of designer outside the bounds of design?

Because a lot of the strategic decisions that you’re talking about making, often, especially in a smaller company, you’ve got to go all the way up to the CEO before you have somebody who has that level of power, and designers have to be invited into those conversations, to Peter’s point, by product people, by business people. And some designers may need to reframe their understanding of themselves and their work in order to make this transition.

Erika: Absolutely. yeah, and I think a lot of design schools need to change. None of us here were educated as quote unquote designers, right?

Peter: Journalism, anthropology, and you’re philosophy…

Erika: Philosophy

Peter: …what, philosophy? So, you just like to ask questions.

Erika: Yes, I do. And teach people how to ask questions because nobody is incentivized to ask annoying questions.

Jesse: I want to ask about asking annoying questions, because Peter touched on the idea that people outside an organization have more latitude to ask questions than those inside because of the constraints of the power structure and power dynamics. To what extent do you feel it is the role of design across all contexts to be questioning the fundamentals of whatever the business context is that they’ve found themselves in?

Erika: I think that is central to the work. I think if you’re a designer, you’re a person who asks questions. I think you can be a craftsperson and not ask questions. You can be a stylist and not ask questions. You can be a maker and not ask questions, but I think if you’re a designer, that word implies a certain amount of power and influence.

And the systems we’re talking about designing now are so complex that it’s very, very rare that the designer is an auteur in the way we used to think about it. Like our idea of a designer. Oh, a Paul Rand or…

Peter: Dieter Rams or something.

Erika: I just think the things we’re designing, ‘cause they are systems, they’re beyond any one person. So I think that being the person who frames the problem, being the person who asks questions, that is core to calling yourself a designer.

Jesse: Problem framing, problem reframing, mean that any internal design leader necessarily takes up this, yeah, permanent antagonist role among the senior leaders of an organization, because they are the one who is there to question what everybody else is putting on the table.

Erika: Yeah, but is a questioner necessarily an antagonist?

Jesse: It’s very difficult not to be received as an antagonist as a questioner, I can say that from experience.

Erika: The practice of design is creation and criticism in dialogue with one another. And I think we’ve emphasized creation and completely lost the sense of criticism, even though that’s fundamental, that’s one half of that dialectic. And I think it’s necessary to do the best work, to create positive change and people have to get comfortable with it and not think of it, like an antagonist.

Peter: We’ve delegated criticism to AB testing or other forms of after-the-fact validation as opposed to the work itself. Because companies are willing to change based on metrics. But, the only criticism that happens internally is crits within a design org, but not say within that broader product development practice.

So you talked about the role of design as being creation and criticism. And I also see the role of design as humanism, we’re bringing a humanistic lens into an environment, primarily dominated by business, whatever that means, metrics-driven thinking, data-driven thinking, or technologically minded thinking. And so, I don’t even know if it’s necessarily questioning so much as it is a new or a different mode of inquiry, different mode of framing. Business is a mode of inquiry, business, MBA-ish-ness is a mode of inquiry. There’s a mindset or perspective there, that have become dominant within these organizations, and I think what you’re arguing for, Erika, is design as an additional mode of framing and inquiry.

I mean, we were making fun before we were recording of the social science stuff that you have on your bookshelf there, but it’s bringing with it potentially this whole social science and humanistic mode of understanding that has been, if not lost within organizations, it’s been relegated to a secondary or tertiary status within organizations with market research or other kinds of after-the-fact reactions to what is being done, but not before-the-fact, informers, of what is to be done.

Erika: My primary issue with the field of design right now is that the discussion is so shallow.  I don’t get the sense that the field is particularly coherent because there is research and inquiry being done and it’s completely disconnected from practice.

And the practice has been completely subsumed into, like, business and engineering. And then people talk about the wish for design to have a so-called place at the table, but they don’t mean that, so often. They don’t mean, “I want design to be engaging at this deep level.” What they mean is, “I want business and engineering to listen to my ideas and tell me I’m smart.”

Jesse: Right.

Erika: Right? Because the sad truth, the bummer about confronting what it means to be a designer in our current context, is that it doesn’t have individual ownership and you can’t show it in a portfolio.

And I think a lot of people get into design because they really love and enjoy graphic design. I love and enjoy graphic design. But the part of the work that’s visible, that’s tangible, that’s a very unimportant part of the work at this point.

I think the actual work of design is invisible and complicated and not appealing to a lot of people who came into the field to work on particular parts of the process.

Music break

Jesse: We had a product management person, Melissa Perri, on the show a couple of weeks ago.

Erika: Oh yeah. I know her. I’ve been at conferences with her.

Jesse: Yeah. Yeah, we had a great conversation. And one of the things that she said, from her perspective as a product manager who lives in that world all the time, is that, and I’m going to paraphrase, and I hope I don’t mischaracterize what she said, basically she said that most of the designers that she’s worked with can’t be trusted with the kinds of decisions that you’re talking about, because they will torpedo your business in the name of serving humanity, and then don’t give a shit about the consequences.

How accurate do you think that perception is? And if it’s not that accurate, what do designers need to do to change it?

Erika: I want to meet the designer, like, powerful enough to torpedo a business. I the name of humanity.

Jesse: Well, this is the reason given for why designers are not invited to the conversations that you’re talking about, is that they care too much about people. They aren’t going to look out for the needs of the business. They’re going to sink your boat.

Erika: Yeah. I agree with that because, going back to the very start of our conversation, I want designers to understand that the business model is their grid. Yeah. I think designers are ignorant about business. Because it’s never been presented to them as part of their concern. That’s my whole point.

And so, yeah. Designers will come in and because they’ve been led to understand that their work is only on the user side, they don’t understand that a healthy, functional, sustainable business is actually in the benefit to the customer because how often have we found a product or service that was amazing, great, and user-centered, and wasn’t financially sustainable. You know what happened? It goes away and something shitty and profitable comes in its place. And so what I would tell the designers is, if you are truly an advocate for humans, you will care about the business. Because only if user needs and business needs are truly deeply intertwined are you going to be serving humans.

But designers feel like, “Oh, business is dirty” and fight it. And then they end up in service of its worst aims. Because they have the special, precious identity. So I absolutely agree…

Peter: I see.

Erika: …with Melissa on this.

Peter: Yeah. most designers, without a lot of training or coaching and education, you wouldn’t want to just put them in those contexts or give them the authority to make those decisions.

Erika: It’s not even a lot, the concepts are not complicated. The fundamental concepts of business, the business models themselves are not complicated. Business models are not hard. Conceptually. And then once you understand….

Jesse: Just look at all those MBAs who make them all the time, right?

Peter: They’re geniuses!

Erika: Yeah. So this is the book I’m working on. My next book explaining business models to designers.

Peter: Are you sure you want to say this, because now you’re, beholden to it. Okay.

Erika: I’m absolutely committed, because nobody is talking to designers. Inside of business, people are not talking to them at all, or “Oh, just give me the artifacts.”

Or they keep hearing about the business value of design. Harvard Business Review has been writing… I don’t know if something changed in the publication, but in recent years, they’ve been writing some intelligent stuff about the relationship of customer experience and design and things to the business.

So it’s not conceptually hard, but it is a huge reframing and revaluing. So, from the head, very simple. From the heart and from the identity, because I think as you said earlier, Peter, being tied to the artifacts, that is hard to let go of.

The centrality of the artifact is still a part of a lot of designers’ core identity, and asking somebody to let go of the artifacts that they’ve invested their identity in, that is significant. That takes time. That’s not going to happen overnight or happen at all for some people, if your fundamental orientation is, “I make a certain set of choices and my expertise in guiding this set of choices is tied to my identity.” That’s hard.

Peter: Speaking of identity though, I think there’s flip side of that in-house, which is, if designers start reading your book, they develop confidence around understanding business and business models. They start making connections between what they’re aware of and the business. They start figuring out, “Oh, here’s ways that the research that we’re doing could actually drive different ways of thinking about exchange of value.” You know, imagine a moderately complex service system. “We can shift value from one part of it to another and satisfy customers while lowering costs,” and designers start saying this, then you’re going to get a bunch of MBAs saying, “Who the fuck are you? That’s my job.” And those MBAs are going to be like, “Yeah, but did you go to Harvard? Have you worked at McKinsey? Are your spreadsheets going out to the eighth decimal point?”

Jesse: They’regoing to Pat you on the head and say, that’s so cute. Please go back to your desk.

Peter: For the listeners at home, Erika just showed a section of her book that read, “Put an MBA out of work.” But there’s going to be a challenge for the designer, as Jesse was just referring to, even if they are right, even if they are grounded, to develop that credibility so that they are not dismissed, so that they are not marginalized because in applying their background, their understanding, their humanistic design and experience-led understanding to, authentically, honestly, rigorously, intelligently shift the conversation around business, business value, business models, inflows and outflows, they are going to be running up against a different way of considering business, that is more mechanistic. That is less humanistic.

Erika: More quantitative, all of that.

Peter: More quantitative. All of that. I mean, not that the designer’s approach won’t have quantitative in it, but there’s, much bigger, values frameworks at play now.

And, in most companies, those values frameworks are dominated by, uh, mechanistic mode.

Research is an interesting contributor to this, user research, customer research, market research. How does this all get woven together in a way that these newer frameworks, newer foundations, newer perspectives in this conversation are understood and accepted as opposed to just push back and reject it.

Erika: I have an answer for that because so much of my consulting work now is, How do we use evidence to influence decision making? And what you described is just a subcategory of that. ‘Cause I think the big blind spot that a lot of designers and researchers have is taking the tools of ethnography and turning them on the organization, ‘cause the organization is the social context of decision making. So it’s just humans in the same way that you understand humans outside the organization in order to sell products and services to them, or create products and services that fit into their lives and culture and match their mental model.

You take the exact same process and turn it internally. So you go to that MBA. If you genuinely care about your customer, your user and you want to make their life easier, you don’t go to them and say, “Hey, stupid customer. I know better than you stop doing the stupid thing.”

Yeah. That’s not how it works. You’re like, this customer already values this set of things, this set of context is meaningful to them. Let’s position our value prop in terms of what’s already meaningful to them. Exact same process, except building empathy among your coworkers is much harder cause people out in the world, you don’t have to deal with them on Zoom or whatever. I used to say, “You don’t run into them in the office kitchen.” So it’s actually much harder to build empathy among people within an organization, but this is incredibly valuable and completely within the skillset and purview of all designers.

So what you do is you go to that MBA and you say, “Hey, I want to understand your mindset.” This is the questioning, and this is why questioning is not antagonistic because you go to them in a genuine, from your heart, Dale Carnegie, making friends and influencing people, kind of way. And you sit down and you’re like, “I, as a designer, want to make you as the MBA business analyst, whatever, I want to make you feel more successful. And I need to understand your job, ‘cause I feel like I don’t understand your work at all. And I want to understand your work. Tell me about your work. Tell me about your day. Tell me about it, how you see success. Tell me about your concerns and your anxieties.”

And just by inquiring, just by setting aside your own agenda, just by openly asking questions like that, yeah, you are building rapport and you are building a bridge, and now you also know how to frame your work in terms that are meaningful to them.

It’s exactly the process of user-centered design, but internally, and people don’t do this. And if you want your ideas to be listened to, to be taken seriously, you start by inquiry. And so now you can build a partnership and work with them to say, “Hey, I know you’re concerned about business success. I know you’re concerned about quarterly reporting, but whatever. And now, because I understand your world better, I can help bring our world closer in alignment,” or, “Hey, I have a view of customer value that’s meaningful to you.” And if you understand that person, and you’ve really asked questions, you know, to not all of a sudden do this brain dump of like, “Oh, but I know better than you.”

And I’ve talked to designers and researchers who still have this idea about like, “Oh, I know better.” Then the stakeholders, the business leaders, like, we have a special kind of understanding the hardest thing for designers and researchers in this position is letting go of the idea that they’re better than the MBA.

And that is a hard mind shift to be more effective in your own work. As a designer, you have to let go of the idea that you’re better or more special, and then you will be effective and you will have more influence because people inside the organization follow the same rules of relationship building and cognition and emotion-based decision making that people outside the organization do.

Jesse: I think there are a couple of factors to making that transition for designers, that transition in mindset. Part of it is, to your earlier point, letting go of what can feel like the moral high ground as the stewards of humanism and humanity in the organization, the ones who were always there to remind people to do the right thing.

Right.  And then the other part of it is letting go of the idea that your value comes from having all the right answers and embracing the idea that your value comes from having all the right questions.

Erika: Yes. Oh, thank you. Yes. That was like a gift. Exactly.

Music break 2

Jesse: So a lot of the folks who’ve listened to this show are in-house design leaders who manage teams of designers. And what we’ve heard from some of these folks is that they are able to establish these cultural values within their own design teams, but then when their folks go out and engage with their partners in other parts of the business, there’s this real culture conflict that comes up.

It reminds me a little bit of the situation that I frequently found myself in at Adaptive Path where one thing that I insisted on is every designer presents their own work. Which meant that I sometimes was putting very junior designers in front of very senior stakeholders.

And then I had to explain to the stakeholders why they needed to listen to my junior designer. And part of that was just getting them to understand that our junior designers are not like your junior designers in-house. They have a very different mindset and a very different skillset. But part of it, I think, is just opening the door to engaging with a different culture on the part of these stakeholders and the role of the design leader in this I feel is somehow to create that opening, create that space for a peer or business stakeholder or a partner to even consider what your designer has to say.

And I’m curious about your experience, especially as a consultant, where you’re engaging, I mean, you’ve been a design consultant for many, many years now, and engaging with these organizations as an outsider. How does an in-house design leader build that credibility? Not just for themselves, but for their entire team, so that all of their partners across the business take all of their designers more seriously?

Erika: It is harder. It’s a longer process coming from inside than outside because you have the mandate coming in from outside, you know, to come in and say, “Why do you do it like this?” And you won’t get fired.

Inside, it’s the same, it’s one conversation at a time, it’s coming in with a very clear agenda, and this should be easier for designers because designers have the concept in their role of understanding other cultures. So you go to them and you say, we want to understand you better so that our work serves and supports you. And you focus on the rapport building, but you can’t come in with answers, you come in with questions, but the questions that feel that they come from a genuine place of interest and support, and that is so powerful.

I do that simple exercise when I run workshops. And I’ve run a lot of, research workshops with in-house teams. And I just have them interview each other about your boring stupid job for 10 minutes. And it is so powerful. I have seen, like, all teams and organizations change after 20 minutes of, “Oh, we’re going to ask each other what you did at work,” which sounds too… everybody wants a named methodology, a technique, a silver bullet.

It’s talking to people and more importantly, it’s listening to people, which sounds so boring and cheap and like it shouldn’t work, but the most powerful way to influence somebody is to not care about looking smart.

This is every in-house, external, whatever. That’s every designer’s issue. I” have to prove how smart I am.” You have to set that aside and say, “No, I am genuinely going to value and listen to this person in front of me.” There is nothing more powerful than that. And that’s what will make you smarter. That’s what will make you more effective.

Now coming to them and saying, “Oh, I’m going to prove something to you.” I turn down every engagement where somebody comes to me and says, “Oh, I want to work with you on this so that we can prove to the CEO how smart our team is, how accomplished, how much knowledge we have.” I’m like, that’s a losing proposition. You have to listen to them like really deeply and intentionally and, and, completely seriously listen to them and that’s powerful. And then you’ll know that at some point you can come back and demonstrate that you heard them, and it’s not like fake, active listening, surface bullshit.

It’s really caring and really hearing. And if you do that, you can change people’s minds. You can change organizations. I’ve gone in and done it coming in from the outside. It’s possible from the inside. It’s not easy. It’s annoying. It’s not ego-supporting, but it works.

Google did that big two-year Project Aristotle study or whatever. And they found out what makes teams go is psychological safety. You know this from your work at Adaptive Path, you know how much fear there is, how people are just afraid of letting their guard down in front of each other. And that’s what leads to bad work and bad working experiences, and people can’t critique and criticize each other’s work unless they have that trust. Which means, if you don’t really want good things for everybody you work with, then you can’t criticize them, and then shitty stuff is going to get out into the world, because nobody’s going to stop it. ‘Cause you don’t have that kind of relationship within your organization.

Peter: You just talked about, how it’s easier to empathize with your customer than with your colleagues. What strikes me is, not what you’d expect, right? You’re working with these people, you’re collaborating with them. You’re trying to get stuff done with them.

It should be easier to empathize with them, ‘cause you have a firmer understanding of their context. But I also know what you’re saying must be true because it comes up again and again, it’s become almost a cliche to say about designers, that they have way more empathy for their users than their colleagues. And I’m curious if you have a hypothesis or even data, evidence, as to why it’s easier to empathize with the person at the other end of your product or service than someone you’re collaborating with to make that product or service.

Erika: Oh, yes. Oh yes. I have an answer because, often your interests are much more aligned with somebody out in the world because of the way organizations structurally put people in opposition to each other. And part of that is the framing of answers being more valuable than questions, individuals and teams within organizations are often in competition for whose idea wins. Sometimes explicitly, sometimes you have brainstorming meetings.

I think people should never brainstorm ideas. People should only brainstorm and prioritize questions, because when you brainstorm ideas, you’re putting a team in competition with each other for who’s smartest. because of the way the organization incentivizes people or recognizes people or funds people.

The way relationships are set up, so it’s not bananas that you would have a harder time empathizing with people, because a lot of times you’re next to each other, which means your differences are highlighted more, ‘cause the differences are tangible every day.

Whereas the customer, right, the only part of their life that you intersect with is, like you said, the 15 minutes they use your product. The rest of the time the customer could do whatever, they could listen to music you hate, they could, like, like food you don’t like, but in an organization you’re up against each other all the time.

Peter: Yeah, it’s a little bit like that Upton Sinclair quote. It doesn’t pay me to understand you, so I’m not going to learn about you because if I actually understand you, because of how things are structured, I might somehow lessen in the overall context of the organization, cause I might be enabling your success. And somehow our organization has set that up as a bit of a zero sum game. So, your success means my less success because you’re the one now getting the plaudits, the recognition, you get a promotion, et cetera.

if I help you do that, at best I’ve remained flat, but at worst now I am secondary. I am a sub to you. I hadn’t thought of it that way, but that makes a lot that’s sense.

Well, we talked a lot about, cultures within corporations, within organizations. And one of the challenges that design leaders face is that, we’re all the product of decades of experiences that have acculturated us, and design leaders tend to have a different set of experiences than product management leaders and engineering leaders and marketing leaders.

And so all these different cultures are expected, now with psychological safety, to collaborate. They don’t recognize just how different perspectives and starting points are of all these folks. And very little has done to try to ameliorate that or mitigate that.

Erika: Yeah, it should be somebody’s paid job to essentially do interaction design on internal communication, but people act like that should just happen, and it won’t.

Peter:  Thank you, Erika, for joining us.

Jesse: Anything you want to plug while we’re here?

 Erika: Yeah. If you want me to come in and help your team make better decisions or yell at any particular subset of people, that’s what I do. I’m a consultant.

Peter: Excellent.

Jesse: Thank you so much, Erika.

Erika: Thank you. This has been fun.

Jesse: You can find Erika’s company Mule Design Studio at http://muledesign.com. You can also find me and Peter on the internet. You can find us on Twitter. You can find us on LinkedIn. He’s @peterme, I’m @jjg. You can find past episodes and transcripts for this podcast on our website, http://findingourway.design/. We’ll see you soon.

Billie: The conditions that are required for a more just world line up as the same conditions that are required for a more successful, more creative, more innovative technology team.

Peter: I’m Peter Merholz.

Jesse: And I’m Jesse James Garrett,

Both: And we’re finding our way…

Peter: …navigating the opportunities and challenges of design and design leadership.

Peter: On today’s episode of Finding Our Way is my good friend, Billie Mandel. Billie has an illustrious career in design leadership, and team coaching and UX teaching.

Billie: So I got my start in tech in the first dot-com boom. And like many of us, I started as a refugee from academia. I was working on a PhD in political science. I was studying political behavior and comparative politics.

So I started my tech career along with 20 other people who doubled the size of Ask.com on one day. And at the time, the company had proof of concept as a search engine and suddenly corporations realized that they could pay us to make a custom that thing so that their users could ask a question on the internet and maybe not charge the company 50 bucks every time they called up.

So I was hired to be what they were calling at that point, a content editor, and to lead a team of people the way we started. So UXC, but it was not UX.

There were 20 of us who were hired on the same day to start building these things custom for enterprises. And, as things were back in the late nineties, within a year I had a team of 50.

Peter: That you were in charge of.

Jesse: Wow. I mean, talk about being thrown into the deep end of leadership. Had you ever led a team before?

Billie: Had I ever led a team before? Well, the way you lead teams, when you’re  the resident assistant in a college dorm, and you’ve got your finance manager and your kitchen manager. But had I ever been trained as a manager?

No, absolutely not.

Peter: Did they provide any training or were they just like, no… Okay,yYou’re laughing. So, no…

Billie: I mean…

Peter: “You seem capable, here, just have more responsibility.”

Billie: The thing about the first.com boom, there was the work that needed to get done and whatever you were interested in doing and capable of doing, you had the opportunity to do.

Jesse: Was leadership something you raised your hand for?

Billie: Yeah.

Jesse: Why did you want it?

Billie:  I’ve always gravitated towards people management, people, leadership, and maybe some of it has to do with being interested in the social sciences and believing that humans knowing themselves better and knowing each other better and being intentional about how we organize and what the rules are under which organize and what the agreements are we make. I’ve always believed that that creates the opportunity for human creativity and social change. And I found pretty early that the desire to see those connections and create those connections and help other people orient when they’re confused, and to give people guidance in combining their super powers rather than fighting it out, I think that’s something that I developed an aptitude for and an interest in pretty early on.

Jesse: One thing that we hear a lot from design leaders is the challenge of staying close to the creative work as you move into leadership. That the responsibilities of leadership start to take over your time, your attention, your energy, and so forth until those kinds of creative decisions become something that you have to really fully delegate to other people, and you aren’t really having the level of creative influence that you had when you were a designer. But it sounds to me like at least through this phase of your career, you’ve been able to maintain some connection to the creative work, even as you were moving into more and more leadership responsibility.

Billie: I definitely have stayed close to the work and the decisions that feel creative to me.

In my coaching practice, I also hear a lot of leaders saying they’re struggling to stay close to the creative work, and, well, sometimes they mean I miss just sitting down and getting into the zone and figuring out if this is the top layer, what flows come next and what flows coming back, that obsessive fun interaction design zone that is enjoyable for a lot of folks, a lot of people miss that.

I don’t necessarily miss that as much. What I’ve seen as most important in terms of staying close to the creative work is maintaining the ability to care and the ability to ask hard questions and engage without being attached to the outcome. So, I think that’s become one of my favorite things about being here. And an educator role is everybody brings me their creative problems that they’re solving. I get to engage and get my hands dirty and get my brain dirty. Understand what kind of problem are you trying to solve? How far have you gotten, where are your blind spots?

My favorite thing to do is to help fill in people’s blind spots and get a more complete picture of the problem space that they’re working on. To me, that’s one of the most fun things we can do, is use our experience and our designer brain to help add and fill in blanks and create context for other creative professionals.

Peter:  Atlassian was your most recent full time job, if I understand right. You were brought on in kind of a, maybe not unique role, but not yet widespread role  of design education, helping the design team do what they do better.

But you’ve also mentioned teams and team building. And I think that was something you did at Atlassian. It’s funny, you mentioned your PhD or near PhD,  political science, and how do people work together to achieve, accomplish, and  come back around 25 years later, thinking about how people work together to achieve and accomplish.

How do you approach teams and teaming?

Billie: Ah, this is my favorite topic. This is my favorite, favorite, favorite topic. It’s so interesting because the job that I came to Atlassian to do was design education. And when I started getting in deep with the designers and the design teams and their cross-functional collaborators in engineering and in product management, one of the things that became so clear to me is that it wasn’t, How well do they use Sketch? How consistent is their design system? You know, Are they writing good code?

Software teams aren’t limited because they don’t know how to code or they don’t know how to make wireframes. They’re limited because they are not as effective as they could be at combining their ideas and their proposals with each other.  This is my big Aha! In the past three, if not five years. If teams are struggling,

it’s probably because of their teamwork more than it is about their craft skills.

Peter: One of the insights I had at some point in my career was reflecting on my degree in anthropology, which felt, for the longest time, utterly disconnected to my work, and realizing, Oh, Oh, wait a moment. That actually, was a pillar in my foundation of what became my career, later doing user-centered design, human-centered design. I’m wondering what, if anything, from your academic development and understanding, have you brought forth?

Billie: It’s amazing. Now at this point in my career, now that I, have really found my focus and the work that I want to do, the work that’s my work to do in this world feels like helping teams be more effective, helping teams hear all the voices of all the people on the teams and value them all equally and maybe have the most effective or the most valued idea not come from the person with the largest amount of bona fides in the room. And now I get to bring in everything from what I studied academically in political behavior, political sociology.

These ways of understanding human behavior are super helpful in getting us to be a little bit more critical about what do we do at work, and why, I think, right now, one of the things that’s most exciting to me is seeing our industry start to take inclusion seriously for the first time.

And one of the themes that I’m hearing more and more in the coaching work that I do, and in connecting with other folks who are doing more directly work in diversity and inclusion.

One of the things that’s most exciting to me is seeing the conditions that are required for a more just world line up as the same conditions that are required for a more successful, more creative, more innovative technology team. That, to me is what I’m on fire about right now.

What I’ve learned, is you’ve got a whole team of people and you need to hear all of them in order to make it worth everyone’s while. Wow. Amazing. Those are the same conditions that create improved inclusion. I think that gives us a big opportunity in this historical moment to make those connections. So, I’m excited.

Jesse: So to my mind, that kind of stuff often comes back to culture and the tone that leaders set in their organizations for how voices get included and how decisions get made. And I’m curious what you’ve seen, some of the struggles, some of the successes, whether from your own practice,as a leader, or other leaders that you’ve worked with, in creating that sense of inclusion within teams.

Billie: The most important thing that I’ve seen is that, just like our children, our employees and mentees will do what we do, not what we say. And the most common mistake that I see is leaders grandstanding about, “we want you to do this, and these are the values” and bla bla bla bla bla bla bla, from a perspective that’s facing outward and talking down and telling, but those same people, not walking the walk.

Peter:  So, I really want to be the woke leader, but I also know that I’m a middle-aged white dude, and I’m likely going to behave in not so great ways. 

How does a legitimately, authentically desiring leader, who is demonstrating these behaviors unknowingly… Who’s calling them on it? How do we set up a context internally so that they can get some reflection and be called on it?

Billie: Like any other life-sustaining habit, using your superpowers for good requires practice and requires a critical perspective. So, thing one, I’m going to say only leaders who choose to lead with vulnerability actively and regularly will be able to lead to real inclusion. And I absolutely believe that. And I don’t throw down “only”s and “never”s and “always” very often, but I absolutely believe that. I think you must have the ability and the willingness to look critically at your own behavior and to choose to be better.

Probably the most important leadership and professional book that I have is Mindset by Dr. Carol Dweck. And I reread it about once a year to see the ways in which my beliefs about my own inherent goodness, superiority, and talent are holding me back and causing me to probably be propping up systems that benefit me unfairly.

So, I think every leader, particularly a leader who is from a majority group, you need a trusted dissenter. And that person needs to be somebody who will tell you when you’re full of shit, who is keeping an eye out for what you’re missing and who has a perspective that’s different from yours. It’s a thing you and I have done in our friendship together over the years, Peter, that I really appreciate.

Peter: I’ve been fortunate that I’ve had those people in my life, professionally, who’ve been willing to call me out on my bullshit, and however defensive I am at the outset, I usually over time realize like, okay, yeah, they’re right, and I learned to take that in, but I think a lot of people don’t have that in their lives or they wouldn’t know how to find it. It’s not something you go to your HR business partner and say, “I need someone to call me out on my bullshit. Can you find me one of them?” Like, so any tips on how to develop that?

Billie: Yes. I have a few ideas. So, I do believe that any leader who wants to create an environment of inclusion and who wants to be able to make use of the team creativity that you get by having that environment, you need to create an environment of regular productive critique, and you need to participate in it yourself.

Jesse: What does that look like? Your participation. Does that mean offering your workup for critique or are you simply serving in the role as sort of arbiter

Billie: Oh, no, it absolutely means that your stuff is on the line. So, to me, one of the most important questions a person on a team can ask their teammates is, “What am I missing?” So this idea that each person on a team has a perspective, and I call this the alchemy of teams. If the three of us are on a team and one plus one plus one, there are three of us. But if we’re all like, well, Jesse’s got that bright red hair. And so he’s going to be the leader because he is, he is forceful.

So we’re all gonna follow him. We all do what he says. One plus one plus one is one. So we do what Jesse says, cause we want to impress him. And we essentially subtract the value that we could have added from the ultimate value the team creates. So the conditions that we want are one plus one plus one is more than three, when the three of us get together and combine our passion and our creative vision. We want the output of what we create together to be bigger and better than what any one of us had brought from the start. The conditions that you need in order to do that as a leader, you absolutely need to be willing to submit your own work and decisions, both to your peers and to your team, to get their perspective, and you absolutely have to do it from a place of honesty.

It can’t just be like, “Hey, what do you think? All right, great. We’re going to do what I wanted in the first place.” As soon as you do that, you’ve demonstrated to your team that you actually don’t give a shit, so the way you would do that as a leader is, you’ve got some kind of critique practice and critique practice is my jam. It’s the thing that I do the most and that I’m working on a book and I will have more tools available for folks to use.

Really, the best thing that you can do is, “Here’s what I’m working on. Here’s what my best thinking has produced. Here’s how far I’ve gotten. This is the part that I’m less than confident about.”

One of the most counterintuitive, but I hear the most high value, parts of my method is, shine a light on the ugly part. When you’re showing your work to people to get their input.

What most of us do is like what our kids do when they bring us a picture. “Do you like it?” Which is great when it’s your kid. But if you bring me something, I mean, Peter, you and I have a good friendship. If you bring me something. And you want to know what I think you don’t care if I like it. You want to hear what you’re missing.

So what I encourage folks to do is to ask, “Here’s my best thinking, shine a light on the ugly part. This is what I’m concerned about, and what I’m afraid is going to happen. Help me make sure my butt’s not hanging out in this way. What am I missing?” And you’ll find, as you ask that of the people on your team, and your peers, you will start to find who are the folks who are really going to tell you what you’re missing in a way that helps you move it forward, but you’re right.

You absolutely have to be willing to hear the answer. To me, most of the core of developing comfort with the answer has been in mindset. I’ve shown someone my work and it’s not landing. Why does that feel so crappy? Most of the answer there is because I was taught to believe that if I’m not brilliant and talented, I’m nothing. So therefore if my work is not brilliant and talented at the get-go, how does that make me a value?

Peter: The curse of the honors student.

Billie: That’s exactly right. That’s why I love Mindset so much because it gives us the best possible framework for why these beliefs have served us.

To be honest. I think one of the greatest illnesses in our industry is that while we all talk about fail fast, fail fast, fail this, fail the other. We collectively have no tolerance for failure. We collectively have very little tolerance for showing our mess.

I would bet you money, go ahead into 10 design critiques across most companies in this industry. You’re not going to see sketches. You’re not going to see wireframes. You’re not going to see user journeys. You’re going to see pretty shiny high-fidelity things that people have gone off and spent a whole bunch of time making look the way they think you want it to look. And that’s a huge problem because all the opportunity for one plus one plus one is more than three comes from showing our mess and shining a light on to the part of the problem that requires the most brain power. So if I could wave my magic wand and give all the designers in our industry something, it would be understanding the value that you get from being vulnerable and being able to do the work that we really need to do in those vulnerable spaces to improve.

But it means that we all have to be willing to improve and willing to start from a place of, It’s okay if our first cut doesn’t have all the answers because we need to figure out what the right questions are.

Peter: You were talking about vulnerability, which I don’t dispute.

Billie: Well, good, ‘cause we’d have to throw down.

Peter: Well, there is a counterfactual.

Billie: Okay. Gimme, I double dog dare you. Try and talk me out of vulnerability.

Peter: Well, well, the counterfactual, I’m not trying to talk you out of it, but the counterfactual is the number of seemingly successful leaders who exhibit sociopathy or narcissism. And I’m wondering, how do I make sense of that. Of this demonstration of an almost lack of interest in others or an actual lack of interest in others, and yet an evident ability to engender success. I’ve worked at companies, I’ve worked at…

Billie: I’m going to interrupt you, my dear. I think the variable there is your definition of success.

Peter: Making lots of money.

Billie: That’s the whole point. I think if it’s making lots of money for you, that’s your goal and you’re a sociopath heck yeah…

Peter: Well. I would say growing a business, I’ve worked for sociopathic slash narcissistic leaders, who’ve been the CEOs of businesses, of some success. There’s clearly, I….

Billie: How are those companies doing on innovation or retention or inclusion?

Peter: I don’t know, but I mean, I’m not one to, apply the DSM out of school, but you can look at wildly successful social media companies and the man-children who run them. And there’s a disconnect between that and what you’re talking about. 2.5 billion users is a measure of success.

Billie: A current measure of success for some people. If you’re talking about longevity, if you’re talking about loyalty…   

Peter: I’m not trying to be a devil’s advocate, ‘cause I actually don’t like devil’s advocacy, but there is a model of leadership that is anti-vulnerable.

It seems that can succeed in certain contexts, and I want to unpack that. I don’t want to believe it.

Billie: One could also say, and for the Jewish lady to say this during the Days of Awe, I’m going to throw down and I’m going to throw down hard. One could say for his business initiatives, Hitler was pretty fucking successful.

The amount of power that was required to take that shit down. It was pretty intense. The level of execution that was possible with a machine like that. I know bad, bad metaphor. When you were talking before, it had me thinking about Hannah Arendt and the origins of totalitarianism.

There’s a thing about the division of labor in a totalitarian system that looks a lot like the division of labor in a company that has a sociopathic narcissistic leader. I think if you look at the Banality of Evil, you read Eichmann in Jerusalem, and looking systemically at what makes large-scale atrocity possible. There’s a level of a division of labor and specialization that can be incredibly effective at a large scale level.

Peter: Hmm. You basically compartmentalize the organization like you would compartmentalize emotions, Like in order to deal with this thing.

Billie: That’s absolutely right. So there’s no one person that is making the decision to press the red button. Each person is responsible for a little bit of the decision that collectively adds up to atrocity. And frankly, I do think that what we see in a lot of massive multinational corporations smells a little bit too much like that for my own comfort.

And I do see it showing up in our tech companies. You know, we’re talking about  massive scale of global atrocity, but even if you bring it back down to something more tangible on the daily, I think there’s a commodification of individual skill and then leaving big decisions up to the big brains, that can work pretty effectively to generate a lot of money, a lot of product, a lot of productivity. And I think it’s problematic because nobody is responsible for the ethics of what that totality puts out. Other than the people at the top, who keep their hands clean.

If my hands are dirty as a leader, then I have skin in the game. I’m in it. I understand what the decisions mean. I’m sharing both the responsibility as well as the spoils. To me, if I’m designing a company that I still want to have exist in 50 years, if I’m designing for 150 years, if I’m designing for sustainability, if I’m designing for a different future, I don’t want everybody to have their hands clean, I want everybody to have their hands a little bit dirty.

The way this shows up in design and in technology is designers or developers who don’t have their user flows, who don’t have their user journeys, who don’t understand why they’re just delivering the screens. They’re just delivering the ones and zeros. They can’t tell you how that piece fits into the other pieces, that holds them back in their craft. And it holds them back strategically, but that’s also what enables them to participate in things that don’t really feel right. And that’s what enables a company to bring in diverse people, but not really include them and have it never really feel right.

I think we overvalue the visionary. I think we overvalue the person who can do everything on their own, and then we become dependent on that person. The company that I want to design, the future that I want to design for our industry, world, everybody’s contributing and everybody is sharing the accountability. I think it’s a different definition of success and a different measure that’s going to get us to different decisions about what we value and different decisions in what we spend our time on.

Last one case in point here. Why the hell is it so damn hard, after 25, 30 years of doing this work, and everybody knows your first cut of what you think the problem is and why it matters, everybody knows, everybody knows that that’s not right. Everybody knows you’ve got to do some real discovery, and really understand your customers or end-users perspective before you put in money and effort into building your product. Everybody knows that.

I have a graph you made, that I use to teach, it’s still the best possible visualization. Why you should figure out your options while it’s cheap to do that rather than expensive. But 30 years later, we’re still having the same effing conversation. And every design team in the world is still going, “They’re not giving us any time for discovery. They just tell us, make the thing and we’ll figure it out later. And we never come back to it.” Nine out of 10 teams out there are saying that. So they know they’re supposed to iterate. They’ve got their pictures of your iterative process and your one, two, three, four, five, and your arrows all day. Nine out of 10 of them don’t do it. Why? Because the definition of success and the, way we assess business value, hasn’t caught up to the way we need to be defining it for the future.

I’m not opinionated about that. Guys, this is really fantastic.

Jesse: I think…

Peter: We’re just here to help you testify.

Jesse: …when it comes to evaluating leaders and the impact of their choices and evaluating them against some success criteria, it’s often a question of your scope of reference, because we often see leaders who make choices that are right for their team, but wrong for the product; right for the product, but wrong for the organization; or right for the organization, but wrong for the users.

Or maybe even right for the users, but still wrong for society. And so as you keep sort of scoping out, you start to see these wider and wider ripples of impact of the choices that the leader makes. And so I think your point is a good one, that where that sociopathy tends to take root is often in the organizations that are most myopic about the wider impacts of the choices that their leaders make.

Billie: Yeah, I would agree with that. I would definitely agree with that.

Peter: As you were talking about the totalitarianism and the kind of atomization of activity within an organization, I realized there’s a devil’s bargain as we think about teams and team building, which is we can create highly actualized teams,  and encourage them to behave in all the best ways. But that team is its own little unit and there’s dozens, if not hundreds, of them in some of these organizations and the risk is a hundred highly actualized successful teams, whose efforts when all added up lead to these societally problematic outcomes. Because we’ve broken up what each team is doing, they can feel super empowered, super positive about what they’re doing and how they’re doing it, but there’s still something happening behind the curtain, where all of that effort that’s embraced with genuine idealism still can be shaped and manipulated. Ideally, it’s manipulated towards positive goals, but it’s most often manipulated towards this gestalt where the whole is so different from the sum of the parts that you don’t know, it becomes the Skynet or the monster that just gets unleashed, that even the creators, even the most senior folks, don’t realize what they’ve done, and in the worst of outcomes it can actually be steered or directed towards what we would consider nefarious ends.  

How do we help folks understand that, to what Jesse was saying, those concentric circles out and out and out. Their role, however small, however seemingly focused, it’s tying into something ever larger. And, how do we provide  lenses or views that allow people to get that kind of powers of 10, like in the Charles and Ray Eames movie, so that you’re always looking at kind of multiple levels.

Billie: Yeah. I always call that a funnel of abstraction, another concept that came from political science. If you’ve got the spirit of the law at the top, the letter of the law at the bottom, like the specific statute at the bottom, and the why and what social good it’s supposed to affect at the top, design problems or business problems work the same way, where you’ve got business strategy or the vision up at the top and all the way at the bottom is every specific detail decision that you would need to make.

Most of us are going to have a part of that funnel of abstraction, where we’re most comfortable. We like looking at the system and understanding the why and the big vision. And if we only lived up there, we’d never get anything done. So the way we get things done is we come all the way down. What does that vision mean for what I’m going to do today?

So when I’m teaching, particularly your junior to mids, they will, you know, they’ll start up here. Sure. And then they get down here and then it’s, “Oh, well, what’s your goal on this screen? When you click this, what happens if you don’t go all the way back up?” That’s how you ended up down the rabbit hole.

I think it’s easier to teach your junior to mids, to come up than it is to teach your leaders to effectively come all the way down and back up again, to have people at all levels, interacting in the middle and helping each other specialize, but also stay informed the real contextual details.

So this relates to what you were talking about before, in terms of leaders staying close to the creative work, so that the most effective leaders at a company like that are the ones when were able to, for example, come into a critique session, see the work that an individual designer has done, and if they’re too focused, be, like, “Alright, bring me up a level of abstraction.” It helped me understand what part of the problem have you broken out, and what are the decisions you’ve made, and which are the decisions that you need input on.

The most effective leaders, even if they’re not the ones who are making those detail-level decisions, when they see what their teams have done, can help connect the dots to that big vision and help assess, “Do we make the right call? Do we make the best call or not? How would we be able to tell?” So the idea of being able to move up and down those levels of abstraction, and share context, is how you end up counteracting that tendency for everybody to be a little bit too far away.

There were a few conversations that I think should be happening in every room where there is. Creative work being done, whether they’re physical or virtual rooms, certainly any kind of software design and development. This is another one of those things.

It seems like it’s not brain surgery. Why is it that hard? But for some reason we still haven’t figured it out. Here’s what it looks like. Let’s just talk about the tradeoffs more.

Why are we not talking about tradeoffs? Here’s what the end users need. Here’s what the technology can support now and what it would take to get it to doing another thing. Here’s what the business needs. There’s always going to be some tradeoff. Not that, What’s it going to cost us? What are the trade offs? In any business discussion, in any set of questions about what we should do and why, you’ve got the business, the customers are end users, and you’ve got the technology, and there’s always going to be a tradeoff between the three of them. And you want somebody who can effectively speak for each one, and you want to make a choice, and you want to figure out at what point will we assess, “Have we made the right choice? And when can we change our minds?”

And I see too many leaders who assumed that that’s their domain and their domain only, and they’re doing their teams a disservice because at every level you need to be having those conversations. Even the junior designer, junior PM, and junior developer who are working on fulfilling the requirements for screen X, Y, or Z. Should it go in this order or this order? I don’t know. Usually what they end up doing is, Which one do you like better? Which one have you already done? Because they don’t have the information they needed in order to say, well, okay, let’s go up a couple levels of abstraction. What does the business need?

What’s at stake? If we choose X over Y at every level, we need to empower our people to discuss risks and tradeoffs and benefits, and to be comfortable with their decision making.

I don’t see enough decision-making at the junior to mid-level. So then I see people who are new leaders suddenly have no idea how to make decisions. And they’re guessing. You shouldn’t have to guess. People are covering for too much insecurity. When, if we got comfortable at every level, let’s talk about the trade offs. Let’s put our cards on the table. If we choose X, what are we not choosing?

Jesse: This just highlights that as many things as have changed since you first joined Ask back in the late nineties with no leadership experience of any kind, and having it just put in your lap and being asked to sort it out, I think that that is still the case all these years later. That there are many, many design leaders who have not had the opportunity to really exercise the muscles they’re actually going to use as leaders before the role was given to them.

Billie: I think you’re absolutely right. This also gets into why you hear so many leaders waxing philosophical about the days that they got to do the creative work, because they become people managers where they just have to give performance reviews. If we worked decision-making and peer leadership and modeling more into our junior to mid-levels, We wouldn’t have that much of a crisis of what leaders are supposed to do.

Peter: Yeah, that’s interesting because we explicitly don’t give them authority, And I don’t think I thought about what is the progression of decision making ability that you want to encourage within people as they develop. I actually am working with a client and we have this fairly bright line between—and I’m responsible for it, so I might be guilty here—we’ve created this fairly bright line between a senior designer and a lead designer. And that bright line is one of leadership, is that ability to direct others, and there’s recognition that the senior designer is a very strong craftsperson, but doesn’t lead others.

And then the leader has that ability to see beyond themselves, and affect the work of other people. Which feels like a quantum distinction, but what I think you’re saying is that it shouldn’t be. It’s almost not fair to say, “One day, you don’t get to make decisions. And then the next day you’re responsible,” without having provided some path to that.

Billie: Absolutely. If you think about it, even the most junior designer is making decisions. You’ve got a design system and you’ve got a new design problem. Where do you apply an existing pattern and where do you choose to make something new? That’s a basic decision that even a junior has to figure out.

Are we giving them the tools that they need in order to make the decisions that are within their remit? And are we giving them effective ways to you assess what decisions did you make? Are we giving them opportunities in critique to say, “All right. Here’s as far as I’ve gotten with my best thinking, here are the decisions that I’ve made. Does anybody have issues with these things? Am I missing something?” Training people to present the right thing and to ask the right questions. That’s why we have to model it ourselves.

What I’m getting at is the definition of success. So if I want my juniors to still be working here in five years and to be leaders and to have knowledge that they’re able to disseminate, that is more valuable than somebody I would hire in off the street. How am I growing them? What am I giving them to indicate that their investment in me is as valuable as my investment in them?

Another thing that I’ve,got for you. Just my back pocket, a practice that I have found helpful, I was thinking about the thing that you said about finding a trusted dissenter. A practice that I’ve started with some of the people I’ve developed a closest peer relationship with, the people I’m working with most often, is a cadence of “more of, less of,” So, a lightweight way to offer feedback to each other, like once a month, once a week, or whatever.

“Hey, we’re working on this thing together. Can you think of anything that I could do more of, or less of in this next round of whatever to help our working relationship.”

It’s lightweight enough that if you get into a practice of it, it’s kind of like Pilates. You’ll develop that comfort with discomfort muscle a little bit.

Peter: I’ll take your word on anything having to do with Pilates.

Jesse: Pilates is great Peter, you should try it sometime

Peter: Sure.

Jesse: And that wraps up another episode of finding our way. Thank you to Billie Mandel for joining us, you can find Billie on the internet at http://billiemandel.com.

You can find me and Peter on the internet too. You can find us on LinkedIn.

You can find us on Twitter. He’s @peterme, I’m @jjg.  This podcast has a website, http://findingourway.design/. There you’ll find every episode, every transcript, ways to contact us. Please reach out, send us your feedback. We live and die by it. We’ll see you soon.

Peter: Vulnerability and trusted dissenters…

Jesse: Totalitarianism…

Billie: Only you can get me talking about totalitarianism on a leadership podcast. I fucking love you people

Peter: You know, you gotta, you gotta get past the surface layers of that onion. You gotta keep peeling it to get at the, at the, at the real stuff.

Melissa: So, how do you learn, how do you instill a product culture when even your leadership doesn’t know what that means?

Peter:  I’m Peter Merholz.

Jesse: And I’m Jesse James Garrett,

Together: And we’re Finding Our Way,

Peter:  Navigating the opportunities and challenges of design and design leadership.  

Jesse: On today’s show, despite some audio difficulties, product management consultant and educator Melissa Perri joins us to talk about the view of design from the product management side of the table, the true value that product managers bring to the process, and how designers can collaborate more effectively with their peers in product management.

Peter: We’ve heard from many people and we’ve had our own experiences of challenges between product and UX. I’m curious what you’ve seen in relationships where product and UX, or product and design, are working well together. What is the agreement there? How do they divide up the work, divide up decision making is often a big issue. Who has the call to make certain decisions? What actually works for a healthy relationship between people in those roles?

Melissa: You have to be partners. I’ve seen lot of bad archetypes and it comes down to being partners and seeing yourself as equals, the two halves of it. And the product managers, I try to explain, you are going to be working with designers super closely.

There are certain activities we are going to divide and conquer. Either one of you could do it, but you have to come back and talk about it together. And then there’s certain other things like wireframing, where you should just let your designer do it ‘cause that’s their job, because you need to be going to do the roadmapping and yeah, and making sure that it’s technically feasible to do things, and making sure that we have the launch plan with marketing in place, and making sure that you’re presenting up to the executives, and getting buy-in for your stuff and then scoping it into the business case and figuring out the goals. 

And, the designer could be part of that too, but you have a lot of work over here, and I see that where, where product and UX start to get tense, is because the product manager is trying to do all the design work and all the wireframing and the journey mapping and everything like that. And the designer is, “That’s literally my role.” And it’s because the product manager doesn’t understand that their role is actually all this other stuff that I just listed, not necessarily just the wireframes. Like the basics of wire frames. Yeah. Important.

Just so you understand how users flow. It doesn’t mean that you should necessarily be the one doing that all the time.

So I think there’s this discrepancy between, what should I be doing? versus what should I know how to do or be aware of? A good working relationship I’ve seen on a team level is when a product manager and a UX designer are working really closely through discovery. We plan our research together. We plan our personas together. We are developing these things as partners, right? Yeah. And then as we start to move into the solutioning phase, the designer is going to lead around really understanding what that’s going to manifest as screens or experiences, where the product manager, giving input from a business perspective to say, these are how we have to think about these solutions to meet our objectives, to make sure that we could still function as a business.

But you’re also having that healthy tension where you’re like, let’s just make sure that we’re doing right by the user as well. So what can we do to solve users’ needs, that will move business goals, is always how I looked at it.

Jesse: I feel like I have had a lot of experiences with product managers who did not themselves have a clear idea of the value that they brought to the process. And, as a result, I find that I have a hard time articulating the value that product management brings to the process of creating products.

Technology’s there to build the thing and design is there to shape the thing and research is there to understand the people who are going to use the thing. And when I get to PM, I start to have a lot of question marks about exactly why that person is at the table.

Melissa: So as technology gets more and more complex, you’ve got a lot more parts of the company that you have to bring together to launch a successful product out there into the market. It’s not just about designing a great solution. How do I make sure that solution gets launched?

Well, it targets the right people. It gets marketed. Well, all that information gets carried over to how do I make sure it’s priced well, how do I make sure that it’s still sustainable over time? And then how do I prioritize the order of those things, to account for things like that. The cost of delays, scoping, moving into new markets, unlocking the potential of the revenue.

There’s all these different things that you could possibly do, but now you have to evaluate it from a perspective of, there’s money out there. How much money is there out there? Do we have the capacity to actually take that money?

Because we understand the needs of that market, we can do it as a team, and we have a good plan on how we’re going to go out and discover that, and test it,  and actually get into it. So, it becomes a very business-focused role at the top. And sometimes design plays a critical role in manifesting those things.

But that strategy of, Where do you want to go? And what does it actually take to build to get there? That’s where I see product really coming into play. And then the order, in the focus of how to do it. 

When I come into companies to help with a product transformation or something, the biggest issue that I see is nobody’s focused. Everybody’s trying to solve 15,000 problems at once. I always do this thing when I come in. I talk to all the teams and I’m like, What are you working on? I start to map it out. I’m like, okay, let me write down everybody’s highest priority.

And I’m like, Why are you working on it? And then I go up to the next level and I go up to the next level and go all the way to the top. And then you could see at the top will say, “This is the most important thing we can do.” And I’m like, “Cool, 10% of your people are working on that. Why? Right. Like why 10%?” Because all these things come up and nobody’s really forming that strategy of how do we tackle this market, enter this market, or just grow in general. In a disciplined way, placed with an intent. And I think what product does is bring intent into the process at every level, to keep everybody focused around what are the most important things, and product at the top looks very different than products on the team level.

And I don’t think you need, I tell companies, too, I don’t think they need 7,000 product managers. I think a lot of people honestly have too many product managers in their companies and they need more designers. I would say that in a heartbeat.

Peter: I’m laughing ‘cause we talked about this a couple of episodes ago and, I see this again and again: companies having too many product managers and they keep hiring more. And my sense is, product managers are a promise of possible new value.

If you have a product manager, they can now help you create new value. And so if we have more product managers, there’s more opportunity for new value. I don’t know if that’s why, but I can’t understand this desire to just keep hiring product.

Melissa: It’s not that. It’s agile, it’s scrum, that did it. Those companies are the ones that call me. They’re like, well, we have 2000 product managers and none of them have ever done product management before, so we need you to come train them. So, that’s, like, my email inbox literally every day.

And I’m like, so why do you have 2000 product managers? First of all, what are you building that warrants having 2000 product managers? Because you are probably spinning up stuff in solutions that don’t, actually, aren’t a product. So they were a project and he put somebody on it like a project manager. You have to spin it up. And now they moved on to the next thing. So you’ve got like a hundred products just sitting there that nobody uses, or like two people use each one of them. And this happens, especially in the enterprise, all over the place. But what happened is, when scrum came out and everybody started adopting scrum, they all had teams.

And scrum basically said, we need at least one product owner on every scrum team. So they said, okay, well we’ve got 10,000 developers, so, okay. Let’s divide that by five and seven. And that means we have to have that many product owners. But that doesn’t mean that you need somebody there just running every single user story you possibly think of. And most of the time they make those user stories up because that’s how they teach them in scrum.

This product owner role, the way they teach it, too, is very not like the way that I teach people how to do product management. ‘Cause you become, like, a backlog jockey where you’re just, like, writing stuff and handing it out to teams and I’m like, that’s useless, that’s not a product manager to me. It has no value whatsoever in it. 

How do we really pull a strategy together? Where we look at it from a business perspective, a customer perspective, and a technology perspective, make sure it all works and then break it down so that we prioritize it and then enable the team to go after it. And that’s where I think the value is on having a product where I’ve seen them bring value to the team.

I think if you have a great product manager on your team, they’re critically thinking about every single aspect, they’re crazy systems thinkers. And if you are building, especially, a software product and a software company, product touches everything.

It affects the way that you make money in your financials. It affects the way that you would market it. It affects the pricing and packaging, it affects the technology, it affects the design. It’s that piece that brings it all together.  And a lot of people in the other roles, or in functional silos where they’re not thinking about it holistically, Is this a thing that we can usher out, that’s going to be successful in every aspect, not just successful the way it solves user needs, but also the way it makes us money. Or the way that it’s technologically sound, where we can build on top of it for the future. And that’s where I see product managers thrive is when they do that job, not necessarily when they’re managing a backlog.

Jesse: I notice a parallel here between flavors of designers, where you have some designers who are going to be very deep in the concept development, the exploratory strategic kind of design work. And then you have other designers who are going to be very tactical and they’re going to be about crafting perfect artifacts and that kind of thing.

And it sounds like there’s a similar continuum, or tension, in product management between this, it sounds like, a product strategy kind of a function versus, as you described it, the backlog jockey, which is, frankly, the flavor of product manager that I have more often been exposed to, which is really a requirements wrangler. and not someone who really brings a point of view.

And I think that’s the thing that I’m trying to get at, is what is the perspective or the point of view that product management brings to that collaborative process. You talk about holism, and it’s great to have one person who is aware of all the different facets of a problem. How does the product manager bring that sense of holism to the entire team?

Melissa: A lot of it’s in the communication. It’s also managing their expectations of the executives. Where I see a lot of people struggle is talking them through the choices that they have to make as well from a prioritization perspective at the top.

They’re not aware of the trade-offs, and a good product manager presents that from a holistic perspective of, there’s trade-offs in pricing/packaging, there’s trade-offs in the way we market this, and trade offs in the way we design it, so they’re really taking that and speaking that language of the executives, or they’re bringing that perspective back to the teams to help them understand what needs to be done with the solution. 

I see that flavor of design you’re talking about, that’s very strategic. Like, I’ve met them, I’ve worked with them, and they’ve been some of the best designers I’ve ever worked with my life. And I think those people are usually more on the strategy side things, working with the product managers.

And that’s where that relationship really comes out to play. I think when you get into the solution side of it, that’s where I still think you need some oversight around the solution and figuring out how it manifests, or how it could affect other pieces. But, from the perspective of what do our products really look like, and how does it function as a system, into like the user’s interactions and stuff like that, I think that’s pretty much the designer’s job. That’s what they’re there for.

And I encourage my product managers to just get out of some of that stuff and let the designer lead. They should be working with the developers. And you just want to make sure that it’s not going to adversely affect the business needs, or the requirements of other teams, or the dependencies that are around other parts of the organization.

The purpose of the product manager, to me, is to help scope out and prioritize what we’re working on, with intent.

And that’s the piece, the intent behind why we do things, because you could build 50,000 things if you wanted to, but what’s the right thing? 

So discovering what’s the right thing to build is not necessarily a one-person job. I think it’s involving the team in it. And I think the product manager’s purpose is to be the person who can help steer that, and make sure that we’re all tracking towards it and helping represent that right thing back to the board and executives.

So, I think the view that I see product managers bring in there is, How do we unlock business value by solving customer value? And that’s the bridge that I see them bring. Whereas designers I think can definitely be in tune with the business and I’ve seen a lot of them do that. I think they get very focused into the customer value piece and I don’t believe there is any business value without customer value, but it’s what are the layers and the levers that we can pull as a business to help them lock that customer value and make it profitable for us.

The pushback I see from the product side against designers is they’re, like, well, they’re only focused on the customer value, but you know, we can’t run a business, we would have no jobs here, if we only looked at doing what’s best for the customer.

You could have the best customer value in the world, but if you’re not pricing it or packaging it correctly, it could completely kill your company. 

How do we take that customer value and package it into a solution that’s also desirable for our market and feasible and viable, bringing those things back together there.

Peter: I appreciate your use of the word intent as what the product manager brings, as it connects to a definition of design, I think, that comes from Jared Spool and we used it in our book, Org Design for Design Orgs, which is that design is the rendering of intent.

In the past I had thought lot of designers being responsible for the intent as well, but I kind of like this idea that someone’s responsible for the intent, and then design is, How do we take that intent and make it manifest in some way? And you’re locating the responsibility for intent with product management.

As you were defining your ideal product management state, it reminded me of what I would consider almost more old school product. Like we’ve almost lost our way. It had been well understood 10, 15, 20 years ago, and then it’s gotten corrupted over time into these backlog jockeys and that kind of thing.

The role that you’re talking about of product manager is fairly senior. It wouldn’t make sense to have someone with that pricing and packaging, and executive presence and vision, et cetera, et cetera, on a team of eight people, you know, paired with a designer and working with five engineers. That group can make a feature. They can’t really build a product. 

And so what is the relationship between the product manager, that role as you’ve defined it, and the teams doing the work? Is there one product manager working with four teams, five teams, eight teams? Are there still product people on those teams, product owners, or do we not even need that? Is it more you just call them scrum masters, in terms of what you need for a JIRA jockey? You don’t pretend there’s a product person at that level. 

Melissa: If you had asked me this maybe five years ago, my answer would have been, well, there needs to be a product manager on every team. Like, would have wholeheartedly said that. I think the issue is that there does need to be a product manager on many teams right now.

And the reason is just the maturity of the way that we work together. I think if you have a mature team with software developers and designers who, given good direction and intent by a product manager, can then look at things and work together to scope out how work gets done and take the lead on it… don’t think you need a product manager. 

What I think it really comes down to is the maturity of the team and the ability for the product manager to build context with the team and capacity for the team to understand that context and feel comfortable with it enough to make their own decisions.

One of the top things that product owners on the team level have told me is that, “I don’t have time to work on the strategy because all I do every day is answer questions from the developers.” And if you are answering questions from the developers that often, it means that you failed at your job to build context about what you’re building with them, so now they have nothing to really go off of. So of course, they’re going to come back to somebody and be like, “What am I supposed to work on today?” Because you haven’t given them enough of a vision. 

And that’s why I think companies gravitate towards having one product manager on every team, because now the team’s like, “What do I need to work on?” And the product managers were responsible for that, in the scrum terms, and then they just start putting lists on backlogs that are not scoped. There’s no boundaries around it. 

Jesse: Yeah. I think that context-setting is really important because, to your point, a checklist is not a vision and, it can be easy, for I think the product manager especially, to get into this cycle of just feeling like your role is to be the one to keep answering those little detailed questions.

But I notice that that context, I have found often, has been provided by design because design has described the various features in context with one another, in a holistic experience and experience vision that they’ve crafted and are delivering.

And I think that I find that context a little bit harder to come by for myself when it is formulated less from an experiential point of view and more from a functional point of view, and in a lot of ways that mindset hasn’t really left us, in terms of the way that a lot of folks do their jobs.

I wonder about where the experiential and the functional come together and how you see the role of a product leader versus the role of a design leader in the articulation of that context to help drive those day-to-day decisions.

Melissa: Yeah, I agree. 

I always approach it from an experience perspective. Like that’s just how I figure things out, inward to outward, first taking the point of the user. I’ve seen other people in product approach things from more of a financial perspective to see how the business model works. And I’ve seen people do it from a functional perspective of what are all the requirements in this market that’s needed, or from a market perspective. So part of this, I’m saying, is biased by the way that I think,  compared to the way the other product managers are thinking.

But one of the pieces I see in that is, there is a functional requirement perspective from a product brain that you would bring in, where I’m going, “Okay, this market is characterized by these types of people and this is what the needs are and here’s our product over here, and here’s the gaps of the functionality that’s needed to solve those types of needs.”

One of the things that we would do is, having one of our user researchers, super senior designer, very much in the discovery phase that you’re talking about, when companies were exploring their product strategy and figuring out where to go, should we do what she called deep insights with them, where she would go out and we’d break down your hypothesis together. And we provide the context and the direction around it, and she would go deep with the customers and come back with a synthesis of, here’s where the gaps really lie. And this is what’s not holding up.

So, we’d partner on these two things, then, to go, “Okay, you’re discovering all these gaps. I’m thinking about the financial implications of going after one thing versus another thing, and how we prioritize those gaps.” And then once we get to a good point, we start to synthesize that and then deploy it to the team so that they can surface up what are the right solutions to actually solve those problems that we’ve now prioritized at the top. 

Jesse: One thing that was always a part of our practices at Adaptive Path, and has been a part of how a lot of folks have done this work, has been to use prototyping in some form as a way of validating concepts before you get to a fully-baked product strategy. Before you get to that level, where you’re ready to hand something off to a team.

I’m curious about whether that’s ever been a part of your process. And if so, how that has played out in that dynamic, how a vision gets created and held, in that partnership between product leadership and design leadership.

Melissa: Yeah, a hundred percent. For instance, one team, we’d have a director of product. I think we had three product managers underneath there. And they reported up to a VP of Product in a big corporation with many product lines.

The director of product and the VP of product we’re brainstorming, like, what can we do for our product line to introduce a new upsell or feature set? What’s the problem that we haven’t solved there’s actually a lot of money in? And the product director goes out, and research does a lot of market research first to understand if some of these potential ideas actually hold any water. 

Okay, we’ve got some data saying they do. All right. Let’s bring in the design director. Both of these are now pairing together, and we were starting to say, what’s our customer research hypothesis? Are we going to go out there and talk to your existing customers or new customers to figure out if this hypothesis that we found in the market actually holds water?

Go out and do our user research, right. Come back and say, there’s something here. Cool. Now we’ve got the beginning of business case, saying that if we solve this problem, there’s money here. There’s something that we can actually upsell.

Now, how do we figure out what the solution is? To go say, I need a little bit of money to test this, from the executives.

Now we gotta figure out how to solve it. And this is where the design director might grab some designers and say, “Okay, let’s prototype, let’s start iterating around solutions and testing them out there with customers. And the product director also got four other teams they’re working with overseeing, but they’re spending half their time making sure this business case is really coming to fruition, doing some more research, really helping this side, but they’re also enabling the team on the other side. 

Peter: You’ve explained the process here for product development.  You’ve talked earlier about matters of scrum and agile. And I’m wondering if you ascribe to any common product development process, two week cycles, three week cycles, this, that, the other thing, ‘cause what you described, I don’t know if 

I would say it’s waterfall, but you want to figure out what you’re doing before you do the next thing. And one of the challenges, I think, some UX types like myself have, is my desire to think before acting.

Melissa: I feel like anytime somebody is like, “Oh, I need a week to think,” people go, “Oh this is waterfall.” And that’s just bullshit, honestly. I hate that concept because here’s what I see when people take scrum religiously.

When I was leading a transformation at this company, we had 5,000 software developers and 350 product managers I was training who’ve never done it before. And they had adopted this really strict form of scrum. And they were like, well, we have three-times-a-year releases, and we do two-week sprints. And at the beginning, after the first release, we get a sprint zero, which is two weeks to figure out what we’re going to do for the next three months.

I was like, “How can you shove all that into two weeks?” Like, you can’t do that. And they’re like, “Oh, this is the only time that we can’t be delivering.” And I was like, “That’s dumb.” It should just be an ebb and flow where we’ve got this time;  we don’t know what we should be doing.

We have higher levels of uncertainty. Okay. Let’s go make that a little bit more certain. Now let’s go test, let’s iterate on it. And then when we feel high levels of uncertainty, now we can break that down into an iterative cycle to release it. And I think agile works really well if you have some level of certainty around the solution as the right vision or direction to go after.

I think it’s all about shortening the cycles of how long these take, the mount of time that you should spend in the research phase should be proportional to the risk of what you’re actually building. So if you’re building an entire new business line, like, so you were doing the Apple iPhone, you think Steve jobs gave people two weeks to go, “You figure that out.” Like, no. Right. 

Peter: It’s more like 10 years.

Melissa: Right. So it’s not that they’re spending 10 years in a, “Ooh, let me just do some market research” mode and like check the numbers out there. They’re prototyping, they’re putting it out there and they’re making sure that it’s awesome before they go spend all their money launching it and doing all these big marketing campaigns. 

And I think that’s what people don’t understand. There’s things that companies do internally that you will never know about. They want you to think that it’s magic because that’s their selling point, just observing something from the outside and being like, they just do big bang releases, that’s not how that happens. 

Same thing for agile. You just watched people do scrum. It doesn’t necessarily mean they’re successful. 

Going back to, you were saying about, Where did product management go wrong? It came out of all these companies doing a big bang, agile transformation. And they took all these subject matter experts or project managers, and they said to them, “You’re now a product owner.” And they were like, “Oh, we don’t know what that means.”

And, starting about six or seven years ago, that’s where a lot of my consulting came from. And when people now can look and say, “Oh, there’s no good product managers out there,” they’re looking at some of those places. 

Never been trained. They have no product leaders to learn from. I’ve been in organizations with 2000 product managers and nobody, including senior leadership, has ever done that role before. So, how do you learn, how do you instill a product culture when even your leadership doesn’t know what that means?

And that’s where we’re getting companies, I think, misunderstanding what product management is. There is no value in a backlog jockey. I think there’s value in bringing a partner to the team to help determine what the intent is, like we were saying, it’s just that, I think companies adopted these practices, thinking that it was a holistic, and some of these agile consultancies, honestly, sell it like the panacea of the world.

They’re like, “Oh, just adopt scrum. That’s going to make everything great.” And you’re like, “No, that’s just one piece of it.” Like there’s so many other things that it takes to build great software. And you’re just looking at one piece of it and thinking it applies to everything. And that’s where I think we get into trouble with all this.

Peter: You had a quote in your book that I love, which is, “I’ve trained dozens of teams who are using the Scaled Agile Framework (SAFe), and I have never seen it work well.”

Peter: Something your question leads to, was a question that we got a little while ago where, there’s this one design leader in particular, who’s like, “I’m working with product owners who don’t know their job. They’re just essentially order takers for someone else. And so now I, as the design leader, have to figure out why we have these requirements, ‘cause I want to build something that people will use.” And this design leader found herself having to fight this internal set of expectations in order to do what she thought was the right job.

So I’m wondering, based on your experience, what have you seen that allows the conversation to change? How have you gotten companies to let go of this dogmatic view of scrum or agile in the way that you’ve been describing and embrace other approaches? In part for those who might be listening to this podcast, like things that they could try within their organizations to push back when they see that things are evidently not working out. But no one knows what else to do.

Melissa: Especially if you’re on a team, a lot of people just feel powerless. They’re like, “I’ve got no pull here. I’ve got no sway. I’ve got no authority to do anything.” I say the best thing you could do is go ask people what they expect to happen from a metric standpoint when you released that, and then measure if it really did, because now you just started a conversation about it.

Usually all it takes is that first question. What do we expect to happen when this launches? And then what timeframe like, do we expect 10,000 users to signup, do we expect to increase retention by 40%? And is that a six month thing or a two month thing? When you start having those conversations, leadership usually goes, “Oh, I never thought about that.” And then people will start asking those questions, which is great. So I think if anybody’s not managing towards those outcomes, just starting to ask, like, okay. Cool. That sounds great. No pushback. See everybody get angry. I used to be angry like this too. I just get mad at people telling me what to do. Yeah. I’d be like, I’m not going to do it. Like, you don’t even know what you’re doing. Right. And that’s not the right approach, although I’ve tried it, so I can vouch that it’s not the right approach. But your approach is more like, okay, cool,  I’m on board. What is this going to do? What do you think will happen? What are your expectations? It’s just gets the conversation going that you can start roll down into those gaps and it makes people more aware of what they’re doing has a lack of intent.

It was funny. I was just talking to another professor yesterday about reframing things. ‘Cause he was teaching it from a sales perspective and he’s like, “Have you ever had to go into a sales meeting where somebody’s asking for something, and it’s not really what they need, and how do you reframe it?”

And I was like, “That’s literally my daily life.” Um, cause everybody comes to me and they’re like, we want to do a product transformation and we want to train all of our product managers and I’m like, “Great. So what have you done to enable that what they’re going to learn is sticking.”

They’re like, “Oh, what do you mean?” And I’m like, “Okay, well, what kind of product strategy do you have going on? Great. Like what’s the most important things that you could be building?” “Oh, we don’t know.” I’m like, “Okay. So I’m going to teach them that they have to look at that first to figure out how they should be scoping down their work and what they could do in line for the goals, so without that, they’re probably gonna come to you. Like I could train them, but they’re going to come to you and ask for that. So are you prepared to answer those calls?” “Oh no.” “No worries. Okay. So let’s work on that first.”

Peter: At some point, you have to wonder how these companies are in business.

Melissa: Well, it’s a lot of them found really interesting problems. It’s a problem that they’ve managed to solve somehow, that’s just good enough for the moment, that people really need it. And they’ve made a lot of money doing that.

If you’re a startup, and you’re starting this from scratch, you don’t have any runway so you are spending the time to get it right, because otherwise you never make it out of startup phase.

If you don’t do the research, if you don’t find that product market fit, you are never making it to the next phase. 

But when you make it to the next phase, a lot of companies are like, “Oh, I don’t know what to do next.” So they just start spinning their wheels. And they forget to go back and do what they did in the startup mode, which is all that research to really figure out and define what comes next. Because I think they panic, and if you hit the growth stage, taking VC money, they’re like OK, you’ve got five years to IPO. And you’re like, “Oh, I’m making $5 million a year right now. How do we get to 150?” And you’re just throwing ideas at the wall, ‘cause you panic and you don’t go, “Well, how did I get to 5 million? Let me think about it. How do I get to 10 million? How do I refactor some of these things and strategically think through it,” they’re like, “Oh, we just build and we just build.” And I think a lot of people associate more features with more money. 

Peter: Well, right? ‘Cause they can assign a value to it. Even if fictional, but they can put them in a spreadsheet.

Melissa: Yeah, I was talking to my students at HBS, they build teams and companies and stuff. And one of them said, “Well, we got like one beta user and I think they’re great and we’re going to build some more features for them. And we’re trying to figure that out.” And I was like, “Why more features?”

Like what – what’s that do. And they’re like, “Well, we just figured that they’d want more features,” “Well, did you ask them about the features you have? Like, are they using those right now?” They’re like, “Oh, we didn’t actually think about that. I just thought if we had more features, we could charge more money,” and I’m like, “Oh, so for like, what’s the core problem you’re solving, right.”

“Well, yeah, that’s right.” Okay. 

And then they take a step back and they go look at it. But I think we kind of adopted that mentality at scale that more is better, more is more money and doubling down on your core problem that you solve and making that really awesome gets lost in the sauce.

Jesse: Yeah, it feels like if prioritization is going to be such a huge part of the value that you deliver, you have to build up your own prioritization filter for yourself. That’s what you need to be able to bring to that. 

Melissa: To me, like, what you were saying, just that the prioritization framework is product strategy. And when I get a lot of product managers who go, I don’t know how to prioritize those things, because you’re missing that product strategy. And a lot of people go, “Oh, our product strategy, we know where we want to be in five years and we know what we’re doing tomorrow.” And I’m like, “Okay, but what’s in the middle of that. Product strategy is that thing that connects that longterm to what are we doing right now? And what do we have laid out for the next two months?

That’s the piece of the prioritization framewor that’s almost always missing in every company.

Jesse: You’ve mentioned research a few times now, as one of the key drivers of that prioritization for you. I mean, obviously the business concerns are there. But I’ve heard you talk about research a lot more than I think I hear most product managers talk about research informing their decisions.

And I’m curious about what you see as the ideal relationship between product management, research, and design as design and research are often very closely aligned, but it sounds like research needs to be driving product management at least as much as it’s driving design, if not more.

Melissa: Oh, a hundred percent. Yeah. I don’t think you can make decisions without understanding what problems your customers have or where you fall short right now. And I don’t think enough companies spend that time really getting into that. If I was going to build a team from scratch today, the first hire I would do is a user researcher.

When you’re a product leader, you don’t have time to go out and do that yourself, So you have to build that relationship into your team and that role to make sure that you’re getting the insights.

I always look at it as, you’re taking all these different inputs and synthesizing them into a direction. And it’s not necessarily synthesizing it into a solution, it’s synthesizing it into a direction. And that’s the intent. 

So I’m looking at qualitative user feedback. I’m looking at usage data. I’m looking at business financials. I’m looking at revenue, cost drivers of what our current products are. Yeah. Or we’re spending money and where we may need to shift spend. I’m looking at trends in the different markets and competitor analysis, and I’m taking all of that information and I’m synthesizing it into, Where do we go next? 

And that’s not, Where do we go tomorrow? That’s where do we go for the next six months? Where do we go for the next year? And that’s that missing middle piece that’s usually gone from companies, to connect the strategy back into what are the teams doing on a day to day basis.

Peter: One of the challenges I’ve seen is, as companies grow, they have product teams. How those teams are defined will vary by company. Sometimes they are actual products that they’re putting in the market. Often they’re different aspects of some larger service experience. If you’re Lyft or Uber, you’re going to have multiple quote “product teams” working on the rider experience. There’s not real products there. It’s all one product. but, you can’t have a team of 200 trying to work on one thing. So you break them up into teams that are able to kind of digest the work. 

And so these product teams get siloed, they focus on what’s in front of them, their metrics, good product teams doing it the way that you would recommend, in terms that they know the outcomes they want to drive towards, they’re doing experiments to get to those outcomes, et cetera, et cetera. 

And so I’ve seen the role of design to almost run contrary to that siloed product organization and have design really just live across the experience, so that designers aren’t quote “embedded” in product teams, designers are responsible for some end-to-end experience and they intersect and interact with these product teams that necessarily have to have their focus in order to do their job. I’m wondering how you see that relationship between the focus of the delivery of these teams that needs to deliver, especially as these companies grow, these end-to-end services that can get quite hairy and complex.

Melissa: Yeah. I’ve worked with companies that were that way and then I’ve seen it organized more through product lines. I think it depends on which type of products you’re building. Where you’re talking about, it seemed to work super well in the services type businesses that you’re talking about.

I’ve seen other places where it’s not a huge user journey all the way through, and you can break the teams up around jobs-to-be-done. These teams are probably not seeing super specific scope and it’s not so technically complex. The team is almost an experience team, rather than a technical team. 

I find when we do org design with product managers, they typically look to put them around, major jobs-to-be-done, around different products, and if feature sets get too complex to manage, we’ll start to break those jobs up into multiple teams to solve it. 

So if you go into each one of those jobs-to-be-done, are those different feature areas? And designers building for that. They’re not necessarily impacting everything across the area, but when you have a totally intertwined journey, where your products plug into that journey, that’s where I see design sitting across everything. It makes total sense.

Jesse: What do you wish design leaders understood better about the role of product management? That if they did understand it, it would improve their relationship with product managers.

Melissa: Ooh, that’s a really great question. I think one of the things is, how much the other systems come into play in making a successful solution. That it’s not just about getting the screens right and experience right for that perspective. That is a piece of building a successful company.  I teach a CPO accelerator group for product leaders trying to become executives. And I was just telling them, your job is no longer just the success of your product at that position. It’s the success of the company. And I see that’s the tension that a lot of people get into with design leaders too.

I think it’s any leader who’s not seeing themselves as beholden to the company’s success, not just their individual solution or their individual feature success or their product success. And I think when both people are in that mindset, the product leaders, the design leaders, they’re both like, I know I will have to make trade-offs with parts of my design to meet the business’s needs, but I also will sit here and advocate for the customer as well, but I’m not going to be unreasonable. I’m going to work with everybody through this because I know it’s best for the company. That’s where I see these relationships work. And I say that, too, to my product managers for salespeople, because product and sales butt heads like crazy.

I’m like, okay, now you’re an executive. You gotta go sit with that VP of sales and know there may be a feature that you weren’t going to plan. But eventually you might have to bump that up just to make sure this company can survive. If that’s the thing that it really takes, we have to be willing to work with that.

We don’t get to operate in a perfect system. It would be great if everything was perfect and we didn’t have to worry about money, and we didn’t have to worry about anything. We build awesome products that people love and not have to worry about the implications. But, at the end of the day, the company has to survive. Otherwise we won’t get to build anything.

Peter: Thank you, Melissa, for joining us. This was great. I actually learned a bunch, and I suspect others will too. So we’ve talked about your book, Escaping the Build Trap. We’ll make sure that everyone knows about that. Where and how else can people find you?

Melissa: if you want to check out my website, it’s MelissaPerri.com. I run a company called Produx Labs as a consultancy, and an online school for product managers that teaches them what to do that’s not scrum, um, productinstitute.com. And I now have a new class for executives where we’re teaching them how to build great product strategies and really move it to the C suite, at cpoaccelerator.com.

Peter: When, when do you sleep?

Melissa: Never. I was up at like four, o’clock this morning. ‘Cause I was like, I have so many ideas! 

Peter: I, yeah, I was just, I was getting tired, just hearing of all the activities and professional things that you’re doing. Well, that’s awesome. So again, thank you so much for joining us and, take care and see you on the internet.

Melissa: Thank you.

Jesse: As always Peter and I want to hear from you. You can find us on LinkedIn. You can find us on Twitter. He’s @peterme, I’m @jjg. You can also find us on our website, http://findingourway.design, where you’ll find an archive of all our past episodes and full transcripts.

We’ll see you next time.

Sally: Reflecting on it now, I learned so much about my relationship with anger and it really helped me. You know, cause people are trying to kill you.

Peter:  I’m Peter Merholz.

Jesse: And I’m Jesse James Garrett,

Both: And we’re Finding Our Way,

Peter: Navigating the opportunities and challenges of design and design leadership.  

Jesse: On today’s show, design leader Sally Carson of Duo Security joins us to talk about her path to design leadership, growing a design team inside a fast scaling startup, managing your boss, managing burnout, and a whole lot more.

Sally: So I currently lead product design and user research for Duo Security, and Cisco acquired Duo about two years ago now. So I’m now part of Cisco. Yeah.

Peter: And how long have you been at Duo?

Sally: I joined Duo five and a half years ago. Dug Song, the CEO, hired me to build out product design from scratch. They had one user experience designer at that time. But I renamed it to product design at that time, very deliberately…

Peter: From user experience?

Sally: From user experience, yeah. Part of my rationale, why I renamed user experience to product design was to recast it internally within the company, because the engineers and the product managers did have some familiarity with working with the one user experience designer. And I was coming in with a different approach and I wanted to say this isn’t the way that you’ve been operating. This is a different thing, different flavor.

Peter: What was your different approach? How did your approach differ from what they were doing?

Sally: One fundamental difference. I was just able to get resources and budget to actually staff up because I think by the time I joined, it was one designer for maybe 30 engineers and just, you know, that ratio really limits what you’re able to do. I also was intent on bringing in a user research competency and building that out.

So any expectations that had been set in the prior years about how they had operated with the single user experience designer, I wanted to make it clear to everyone that this was going to be a different way of operating, in part, just because we were going to have healthier ratios to start with. So that really changes the type of work that you’re able to engage in.

Peter: So you really wanted just a clean break from the before time to your leadership time.

Sally: Yeah. I’ve found that in general, it’s some of the most challenging work that we do. And we’re talking about driving cultural change. I find it’s easier if you’re working with someone who has no sense of what it means to work with design. It’s almost more difficult if you have someone that has a really strong preconception. They’re like, “I understand exactly what this is,” but their conception of it is different from what you’d like it to be.

Jesse: Enough knowledge to be dangerous, right.

Sally: Yeah. I’ve been interested in, sometimes you all mentioned, change management as opposed to transformation and that nuance, if I remember it’s like the way you defined it, Peter, change management is more like the end state is known and it’s just the process of getting there. Whereas transformation, the end state may not be as well understood. Is that it?

Peter: Right. Exactly. And well, has that been your experience with Duo? Like, were you continually transforming into states that people weren’t quite sure where you were headed?

Sally: It was definitely transformative. There’s an improvisational aspect to it where I sort of had a vision of what we wanted to get to, but the way that I staged it progressively, it did take some, just adapting to the environment at the time, because we were also going through hypergrowth.

So the context was changing. At least every six months, it was a different company.

Peter: Was that a vision that you established when you joined, when it was just you and that one other designer?

Sally: What I came in with was a hodgepodge of what I had seen as best practices throughout my career. Like I think at that point, I would have been about 15 years into my career. And so I had seen one particular shop had done agile really well, and had found a way to integrate design fairly well into agile.

A different shop had healthy ratios, a different shop had really strong research. So I was trying to pluck from the best that I’d experienced and put it together and basically create the design team that I always wanted to work within.

Peter: Had you primarily been in startups up to that point, what was the nature of your background before joining?

Sally: So let’s see. I’m an army brat. I moved all around. Eventually we settled in Virginia and I did go to college. I got a BFA in communication, arts and design at Virginia Commonwealth University in Richmond.

Peter: So you’re a graphic designer.

Sally: Yeah, I got graphic design training. It was really a mixed bag of video, animation, illustration, graphic design, and then amazing faculty that had us reading, you know, Marshall McLuhan and Noam Chomsky, which for my 19-year-old brain was probably mostly over my head. But as I reflect back, it’s come in handy quite a lot, you know, just to make sense of, like, the changing media landscape, for example.

Jesse: How did you find your way into digital?

Sally: So I would have been at VCU in the mid-to-late nineties and there was no web component to my schooling, but I was interested in the web and yeah, I just started doing what a lot of folks at that time did, which was just view source, copy, start hacking it, and figure out FTP.

And then I got really lucky because my first job out of school was a small, educational startup In Charlottesville. And they hired me as a full time illustrator, which is pretty extraordinary. But then when I joined, they found out I knew how to code. And they were like, “Oh, you’re upgraded to multimedia developer.” 

I’m really fortunate where I have this career arc, where if you trace my job titles through the years, it’s a complete parallel to what was happening at large within the industry. Like, I was a multimedia developer. I later was a web designer, interaction designer, user experience designer, product designer, like that is how we all do about our titles through the years.

Peter: Sadly those, Radford surveys that everyone has to use, in order to base industry compensation on, still refer to us as, like, web designers. Cause they’re like way out of date.

Sally: Gosh, yeah, come on, Radford. Get it together.

Jesse: Hey, taxonomy. It’s hard.

Sally: It is. Yeah.

Peter: So, how do you go from being a multimedia developer to a design leader?

Sally: I had plans to move up to New York in the summer of 2001. I rented an apartment up there. And I, found a Polish cyber cafe, and they had satellite internet and that was the only high speed in Greenpoint at the time.

And I bartered with them to get high-speed satellite internet on the roof of my Greenpoint apartment building, by redesigning their website.

Peter: Nice.

Sally: And I worked it out with my boss at the time. That startup in Charlottesville, I was like, I have high speed internet up in New York. Let me keep working remotely. And so I moved up. I lost my job within, I don’t know, three or six months.

They were just like, this remote thing is odd and it’s not really working out. And I was like, okay, that’s fair enough. And then there were no jobs. In New York City in particular, there are no jobs. I was unqualified to wait tables, to, you know, be an assistant, to do any kind of administrative work anywhere.

At the time in New York City, the job ads for anything web-related were like secretary / webmaster. Isn’t that so odd where they’re like, this is just pure administrative work and yeah, I couldn’t…

Jesse: And also, can you configure IIS for us…

Sally: Yeah. Yeah.

Peter: How well can you navigate the shell?

Sally: Yeah, very poorly. 

So I became a bike messenger and did that right after 9/11 in New York for about a year.

It was such an amazing job and it’s such an amazing time to have that work, to get to see every secret pocket of the city that most people don’t have access to.

It was just an adventure. 

Reflecting on it now, I learned so much about my relationship with anger and it really helped me, you know, ‘cause people are trying to kill you when you’re a bike messenger in New York. Like the taxis hate you there. They are trying to kill you. People are doing dumb things that are dangerous. They’re doing scary things that are dangerous, on purpose. And I just learned how much, the more I would engage and get angry and feed into it, it would build my anger, but if I could just let it go and let it wash over me, and not replay the bad incidents in my mind over and over, just really changed my relationship with how I can deal with difficult people or difficult moments, that was helpful for life and for my career.

Peter: For becoming a manager.

Sally: It’s not like I’m fully enlightened. I do notice now, if I’m replaying a situation that made me angry, it just feeds into it. It makes me more upset. You know, I carry that bad emotion with me. It drains me.

Peter: Right. Right. So you’re a bike messenger. At some point you must get back into design and into design leadership.

Sally: Yeah. I was doing a lot of bartering to get things that I needed, still doing design work. And then, the grand finale of my bike messenger career, I did a East Coast bike trip with two friends of mine, two girls from Virginia. 

We were raising money for cancer research. And the three of us rode our bikes from the border of Canada to Miami in three weeks. 

Jesse: Wow. 

Sally: It was too, it was too much, it was too hard, it was nearly a century, which is a hundred miles, every day for three weeks straight. And the first day of that trip was my first century I ever did. Yeah. 

That trip just taught me, How do you do a hundred miles? You really do it a mile at a time. You know, you’re like, okay, five more miles. And then five more miles. And then five more miles you’re just chopping it up into these little bits.

Thanks for indulging me on all the bike stuff. 

Jesse: Well, I think that bike stuff is relevant, honestly, because I hear a lot of  preparation for leadership there in your various travails on two wheels, whether it’s, shaking off the moment-to-moment bad feelings of contending with aggressive drivers in New York City, or just getting up every day and facing another hundred miles on that long ride. Those are lessons in resilience, honestly, that I think are essential for any leader to learn if they’re going to be successful.

Sally: That’s great. Yeah, it certainly gave me confidence.

As we went through the Virginia portion of that ride, some pals of ours rode that leg with us. And this one guy, Ed, was working at a company called Crutchfield at the time in Charlottesville. And I was just chatting with him, riding next to him. And he’s like, you know, we’re hiring a web designer. So call me up when you get back from this trip. 

So then I became a web designer. Crutchfield is an eCommerce shop and they sell high-end audio and video equipment. And I joined right as they were transitioning away from a print catalog business into an eCommerce business.

We were borrowing a lot of ideas around qual and quant from what Amazon is doing at the time. So we were doing funnel analysis, AB testing, tracking conversion metrics.

So that was great for just learning chops around quant informing product decisions. And then we also partnered it with qual. 

Peter: You mentioned, when you joined Duo, the ratios were out of whack. There was one designer for 30 engineers. So I’m guessing early on, you knew you needed to recruit and hire and build out a team.

That was five and a half years ago?

Sally: Yeah.

Peter: I’m wondering if there are stages of your job, stages of your team, how you evolved, how things evolved around you.

Sally: Definitely. But early on, we just needed to grow and we needed to build a team pretty quickly. And I had joined Duo at… I was four months pregnant with my first and only kiddo, so there was also an external deadline, you know, I needed to build up a little nucleus of a team quickly.

Peter: Five months before you were going to be gone for a while.

Sally: Yeah. Yeah. So I was able to make some hires and got a couple of product designers in, got a user researcher in. And really what I wanted to emphasize with the org was the power of user research. And to quickly try to get us to a place where we’re getting beyond strictly usability testing.

Peter: What was the opportunity for user research? What did you witness that was lacking that you felt user research could address?

Sally: Happily Duo was already so customer centric, they really were, so the stage was set in a really great way for me. Because when we’d bring engineers and product managers to observe the usability testing, it, like, pained them to hear the customer struggling and to watch the customer struggling, which was great.

You know, I didn’t have a team that was dismissive of that kind of feedback. 

Peter: I’m curious how you framed the advocacy for user research. I think we’re seeing that it’s easy to build out design orgs because more designers means more assets. The value of user research is less clear, I think, for these organizations, because they’re not making anything, they’re not producing material…

Jesse: It’s less quantifiable at least… 

Peter: Yeah. And so how were you able to advocate for user research and going beyond the expected usability, into stuff that’s more generative? What were the stories that you found that worked? What were stories that maybe you tried that didn’t work?

Sally: One thing that’s been really beneficial for us is to come and present short consumable research nuggets at all-hands meetings. What I really wanted to get away from was, user research goes off for six weeks and comes back with a 30 page PDF.

It’s very participatory. So I think that’s a high level theme. How can we make design and research as participatory as possible, and really bring people along for the ride, co-create together so that they’re truly invested in it. What that might look like for those early days of usability testing are bringing those engineers and product managers into the room and having glass on one side of the lab.

In a hallway where people are walking by, including our cofounders, so that they can see what’s happening in there, generates a lot of interest.

Jesse: So kind of raising the literal physical visibility of the work. By not having it take place off site or in a sealed off soundproofed room that nobody even knows what’s going on behind that door.

Sally: That’s right. Yep., really exposing it. And then, because we’re bringing them along for the ride, getting them excited about it as a unique differentiator for us. Like, I’m not aware of other cybersecurity companies that have this rich investment in design research. So it becomes a point of pride.

Peter: So you mentioned the CEO’s name… was it Dug? I’m curious to hear more about your relationship with him.

If you’ve listened to some of our past episodes, we talk a lot about relationships and in particular for leaders in the position you’re in, there’s a lot of need to manage up and get, maybe not just Dug, other executives also understanding what you’re doing and onboard.

How have you approached that?

Sally: I had done my own internet of things hardware startup prior to joining Duo, for about three years. And he was an advisor and a mentor to me as a first time founder. So I was learning from him directly through him mentoring me, but also just the modeling, watching how he was running Duo as a super successful startup and doing it in a way that’s so humane and customer-centric and people-centric for the employees. So that was wonderful because coming in,  already having had a foundation with the CEO and a relationship there.  

Chester’s my boss, and he leads engineering. And between Dug and Chester, they both are so sympathetic to what design can do, and the value of investing there. It was so helpful for me. It really set the stage where I didn’t have to work, upstream or fight gravity. You know, I was finally in company where generally they understood the value and they understood why I was there.

I had enough credibility that they trusted me to give them things that they didn’t ask for and to show them why that was valuable.

Jesse: How did you earn that credibility?

Sally: I think in part, having had that relationship with Dug prior to working together. But then, you still have to prove it out in your new organization, even if you have the relationships. It’s so key to deliver some quick wins, even if they’re small in scope compared to what you can ultimately deliver. 

And if they’re resonating with your audience, whether that’s executive stakeholders or someone else within the org, really socialize the crap out of those small wins, you’re trying to build out an early portfolio of case studies where you’re delivering value to the business that’s concrete, that’s credible, that’s resonating.

Jesse: Right, right. What is the role of risk-taking for a new design leader in an organization? Because I’m imagining a leader setting out to go get those quick wins. It can be very easy to choose the safest, least disruptive things to do. So how did taking a chance play into your path at Duo?

Sally: Maybe speaking about cycling relates to this. And before cycling, I was a skateboarder, and in the past I’ve been a bit of an adrenaline junkie. 

Peter: Not anymore. 

Sally: Not anymore. I don’t know. There’s so much adrenaline hammering me from the outside world right now that I’m like, I just want peace.

I just want calm.

Jesse: We’re all on a mountain bike right now.

Sally: Totally. Totally. So risk was a big part of it. That’s kinda been, my M.O. is just take huge swings. I can’t imagine being successful in this role without having a big appetite for risk.

Peter: What were some of the risks that you took?

Sally: I had not gotten formal training on being a good leader, a good manager. I hadn’t had any block-and-tackling on that. And I was building out a big team. So for me, there was a lot of learning along the way, just on the basics of being a strong leader, being a good manager, and kudos again to Chester because he has done such an incredible job of building out what he and I sometimes called a “leadership factory.” When you’re in hyper-growth, you have to develop successive waves of leaders, your top talent, ICs that are interested in the management track. How are you going to develop them into managers in 18 months? And. Who are the next wave of directors that could be credible in that role and how can you set them up for success and not extend them beyond what they’re capable of now.

And we all go through the same training when you join as a manager. And, that helps because we have a shared language and understanding. There’s a shorthand when we’re using the same nomenclature, but there’s a really high investment in Duo around professional development. 

I have not encountered an organization better than Duo, that’s better at helping people become first-time managers and then grow their careers from there. It’s very thoughtfully done and we put a lot of investment there ‘cause we want to retain people long-term.

Peter: What, if any, distinction do you make between management and leadership?

Sally: Yup. Oh, this is good, Peter. ‘Cause I feel like you have some thoughts on this if I, if I recall.  And it’s good, ‘cause I think you’ll disagree.

Peter: Well, but I’m wondering because it sounded to me almost like you were using management and leadership interchangeably, and we’ve discussed them as distinct.

Sally: Oh, that’s so good.  I do make a distinction between leadership and management. I think it’s a Venn diagram in my head. There are managers who are not leaders. There are leaders who are not managers, but there are managers who are leaders and, anybody can be a leader in a sense, there are people who are influential over the organization’s culture and they might be individual contributors who don’t have any direct reports, but the way that they carry themselves is either an embodiment of how we all want to show up organizationally, or maybe they’re highly influential over the product or other aspects of the organization. 

There’s a great book that I love called Speaking as a Leader. And I kind of use it as a tuneup every six months. I’ll just listen to like 20 or 30 minutes of it to refresh myself. And it’s so handy because it talks about how, at any given time as a leader, you need to be really clear about what your current talking points are, what you’re saying.  

Being thoughtful about the way you show up and being aware of your audience at any given time. It requires high emotional intelligence, but sort of a different flavor of emotional intelligence. There’s the one-on-one emotional intelligence. There’s also power in reading a room, like the one-to-many kind of emotional intelligence.

Not just being mechanistic and transactional, the way that managers who aren’t leaders can be, but really reading the room, maybe surfacing things that are going unspoken that are too dangerous for individuals to say and using your role power as a leader to go ahead and put voice to things that people who are maybe underrepresented or don’t hold that much power would be putting themselves at risk to say.

It’s easier to train people on management. Are you doing your one-on-ones? Are you building trust with your direct reports? You know, here’s how you delegate work. But it’s a great entry point into leadership at large because management is a little bit more accessible.

It’s a little more like, okay, here’s your checklist. As a first time manager with a few direct reports, make sure you’re doing these things. Just rinse and repeat, rinse and repeat. And you’ll inevitably encounter new challenges, So there’s no real way to practice it without just doing it.

Peter: What are the leadership skills that have been the hardest for you to acquire and learn?

Sally: This is where I get kind of selfish. I’m like, “Ooh, maybe Peter and Jesse can teach me some things here.”

Peter: That’s fine.

Sally: Honestly, it’s been such a joy to be able to hold one position for so many years because there’s things I learned in the course of five and a half years that I wouldn’t possibly have had the opportunity to learn if I had only stayed for two or three years. You know, a product manager might make a key decision on strategy, leave the company. And I get to see how that played out over the next few years. And they didn’t get that learning cycle.

Then I notice how I’m changing, my team is changing, the context is changing right now. 

What’s top of mind for me is energy management. I have days full of meetings and there might be a really important meeting at 3:00 PM where my energy is really flagging. And I’m really just like mentally fatigued because of context switching, so that afternoon slump, if that happens to collide with a really critical meeting, that’s intellectually intense or even emotionally intense, that’s one of my biggest challenges, is just like managing energy. Staying mentally sharp when I need to, right? ‘Cause it’s almost pointless for me to be there if I’m not mentally sharp for some of these conversations. So what do you got for me? You got any advice?

Jesse: Yeah. Well, in general, I think design leader happiness, and day-to-day satisfaction tracks very strongly with the leader’s ability to control their own calendar.

Sally: So true. Yeah.

Jesse: And, to the extent that you are able to create space in your calendar for yourself to give yourself what you need to show up at your highest level of capability, that’s, what’s gonna make you successful.

It’s challenging, though, because in most environments, design leaders don’t have enough authority over their calendar. They are working to rhythms that are set by other departments. 

Peter: I’m a fan of the 20-to-30 minute coffee nap.

Sally: Oh yeah, yeah, yeah, definitely. 

Peter: It seems silly, but if you can take it at the lunch break, if you can give yourself an hour at lunch and you spend that first half hour eating and the second half hour trying to doze, even if you close your eyes and try to ignore stimulus for half an hour and you don’t sleep, you will reset a bit.

Because I’m like you, I’m not great with intellectual energy in the afternoon. I try to do all my intellectual energy in the morning, and then in the afternoon, that’s where I’m doing more kind of administrative stuff. But if I have to do intellectual energy in the afternoon, I will take a nap. If I can get even 20 minutes to try to refill my energy cup, so I can be alert.

You know, I know people who burn out, even when things are fine, ‘cause they just keep working.

There’s a category of person who keeps working, and I think a lot of folks burn themselves out unwittingly, unknowingly. 

That said, burnout is also organizational, contextual, situational, right? Certain contexts lead themselves to burnout. It sounds like Duo is actually not one of those. The prosocial culture you’ve been talking about, I’d be surprised if burnout was a problem, just because of sensitivity that the leadership has had.

Jesse: It sounds like people are really watching out for each other there, which is the big thing that leads to burnout in so many organizations. That there basically isn’t anybody watching to notice that you’re burning yourself out over there.

Sally: That’s right. I’m so lucky the culture is so healthy at Duo and I try to not take it for granted because it has been so long since I’ve been an employee elsewhere. I think Yahoo is really the last place I was an employee and that would have been 2005-6.

You’re making me think of something as you’re talking about burnout. I think I’ve experienced two flavors of burnout. I’ve experienced the one where I’m just simply overworking and maybe something like adrenal fatigue, if that’s a real thing. And some of that for me has been not appreciating my own value. What I mean is I need to over-perform, I need to overdo it, I need to overdeliver because I didn’t have the intrinsic confidence in the value that I’m bringing. And really have worked hard to try to train myself out of that and say, this is what I’m able to give today. And I understand that that’s valuable and that’s why I’m here. That’s why they’ve asked me to be here, yeah.

Jesse: I think that’s a real pitfall, especially for new leaders who are like, “I’m moving into leadership for the first time. I feel like I’ve taken on the mantle of leadership.” Right? And they put all these expectations on themselves about how they now need to show up, that is different from how they were showing up before.

And it’s true. Leadership does have its own set of requirements, but people build that up into this thing, especially that they need to be the hardest-working person on the team by every perceivable measure, in order for them to continue to earn their place at the head of the table, so to speak.

Sally: That’s so true. That’s so true. Really, they’re doing their team a disservice because they need to model to their team taking care of themselves. Taking vacation time, not sending those late night emails. 

Peter: I think a lot of leaders don’t recognize the importance of modeling. They just, they tend to…

Jesse: Do, as I say, not as I do.

Peter: But people do as they do. ‘Cause that’s how we’re programmed.

Jesse: There’s another facet of this that’s related to the culture of leadership and the cultures that leaders establish for their organizations through what they model. You mentioned that you report into an engineering organization. In most contexts, I would say that if I heard from a design leader who was reporting into an engineering organization, I would assume a certain set of cultural difficulties that would come along with thatm of the differences between the way that an engineering organization wants to manage its work and the way that design work wants to be managed, and potentially really conflicting values on the part of a design leader versus an engineering leader in terms of how they make decisions, how they orchestrate the work of their teams, how they communicate.

All of those kinds of things. 

So I wonder what advice you might have for other people who find themselves as design leaders reporting into engineering organizations, for how to manage that relationship effectively. What do you think makes for an effective partnership when design is situated within an engineering culture?

Sally: For me, it really comes down to the leader. So Chester, my boss, has worked with designers before. I feel like on a deep level he groks what I’m here to do. And there’s just so much trust there. 

I’ve learned so much from him talking about modeling and leadership. He’s got such a learner’s mindset. He really listens deeply. He’s open to learning. He will always offer his perspective, but he granted me that autonomy and gave me the space and time that I needed to prove what I was trying to do and to build that credibility. So I think if you’re going to sit within eng, it’s really important to have the right leader as your head of eng. 

Some of the benefits of being in eng, is eng tends to get budget for headcount, so that’s kinda nice. And in the early days, as we were just getting started with my team, we really did want to be in lockstep with eng because they were shipping really frequently. So we wanted to really embed with them, co-create with them. And it was helpful organizationally, so much came for free, was sitting in the same place within the organization, so much communication, there was no silo. 

Then, as we built out research, then the opportunity became, Now, how do you make sure you’re also partnering in a really strong way with product management, as we kind of became more mature, became more strategic. But in those early days, when we were a little bit more delivery/execution focused, sitting within eng, was very helpful. And it hasn’t really been an impediment to us since in large part because of Chester, because of my leader.

Peter: You said you had the autonomy to run your team, as you see fit, regardless of who your leader is.

Sally: That’s right. I’m not expected to run it as though it were an eng team, which is helpful, yeah. So, we were able to demonstrate a different way of working.

Peter: It sounds like when you joined Duo, in terms of things like culture, leadership, you hit a jackpot as a new design leader in an organization where a lot of the challenges that other design leaders face in other organizations just weren’t there.

I’m wondering, though, how, if at all, that changed with the Cisco acquisition. ‘Cause now there’s a whole set of relationships that you didn’t have before, new people that you’re interacting with. How have you had to shift or change how you relate up and out, now that you’re within this much broader context?

Sally: Yeah, I guess the fundamentals are still the same, which is: build relationships, identify who your key partners need to be, and just spend the time to build that trusting partnership. And, I’m happy to say, I haven’t really encountered much in the way of politics at Cisco, which is pretty extraordinary.

‘Cause it’s a huge company. But honestly, like, I’m still learning my way. I’m still finding my way. It’s a massive org and it’s a new set of skills I’m currently developing. How do you seek and gain alignment across a broader organization where you’re not necessarily directing those resources? That’s an interesting pickle.

Peter: So what are some steps that you’re taking to realize that?

Sally: Hm, I think Duo does have a lot of credibility within Cisco. And so using our organization as a model is one. Again, same playbook, build out those case studies and socialize them to demonstrate what we do and credibility, and then really invest in one-on-one relationships with your key partners, just spending time understanding what are their needs, what’s challenging them. That’s been foundational for me. I’m sure if we talk again in a year, I’ll have new stuff.

There is something else on burnout. Can I take us back to burnout for a second? Okay.  ‘Cause I’m again, selfishly, I’m curious to hear what you all have to say. 

Peter: And clearly this is something you’re dealing with. I don’t know why in a pandemic, you would be considering burnout.

Sally: …the smoke-filled air. Yeah. 

Peter: That’s right.

Sally: Yeah, the other flavor of burnout. So there’s the overwork burnout that I’ve certainly experienced at times. And then the other flavor, I suspect particularly as a design leader, is like a creative malaise where part of it is, how do you continue to maintain a creative practice that rejuvenates you so that you can bring your energy and your spirit into leadership? I find that there’s ebbs and flows of feeling lit up creatively, and there’s a form of burnout for me that I encounter sometimes where I’m not particularly inspired. I know I will come out of it because it’s cyclical, but it’s something like a creative malaise and it’s a real bummer when it hits.

And I always know it will resolve itself, but it’s inevitable phase that I have to go through. And it’s always a bummer when it happens. Do you all have that?

Jesse: I think, to your point, I have that less when I have creative work to do, and, as a design leader, your access to creative work is highly variable, and in some cases might be more or less nonexistent for very long stretches of time,  before you ever get to offer a creative opinion, you know, move a thing around on a screen, any of that stuff.

And I think that you touched on something really important, which is that we think of burnout in general in terms of overwork, that if you’re starting to feel burned out, the thing to do is to do less, but, in fact, what it might be is that you’re just not doing the right things, that you’re not doing things that actually fill you up.

That, in fact, what you might need is a little bit less of whatever you’re considering your wind-down time, because it’s not actually replenishing you and you need to go get a hobby.

Sally: Yeah. Yeah. Like I really rely on just taking walks in the middle of the day, so it’s really regenerative for me to take a quick walk outside at least once a day, if not a few times, if I have a little pocket of time. 

Peter: Also following on Jesse’s response, how creative are you in your work these days? You’re running a 30-person organization, product design and research, maybe… do you have content or other functions in your team as well?

Sally: Yeah, we brought in UX writing, UX eng, some design systems, design ops types. 

Peter: Right. So you’ve got a team of 30. And, when I think about people in your role, I think of four sets of activities they’re doing: there’s creative leadership, managerial leadership, operational leadership and I’ve added a fourth. I used to just have those three, I’ve added a fourth, which is this executive leadership, kind of strategic. It’s related to creative, but it’s different, ‘cause you’re setting direction in some ways, or having certain kinds of relationships or conversations. 

And I think a challenge that a lot of design leaders in your position face is, as Jesse pointed out, you’re not doing the creative work, and I’m wondering if that’s been true for you, how you’ve maintained access to the creative work, or if you’ve elected to delegate much of that. When you do do creative work, how do you know where to focus your creative time and your creative energy? What’s your relationship to creativity within your team? ‘Cause I’m sure it’s not what it was when you were two to five people.

Sally: Yeah. Yeah. It’s really different. Now, when we were two to five and maybe up to 15, there would be a Brew:30, Friday afternoons at 4:30. The whole company would get together for happy hour and tap the keg. And it was an extrovert’s dream and all my little tiny baby designers and me who skew more introverted would go hide in our usability testing room and do a quiet drawing hour, where we’d, like, listen to a podcast and not talk, and draw together.

And it was the cutest and it was so fun. And outside there was the hum of people talking to one another and that was kinda nice, like that added to the ambience. But I love that quietly stealing away into our little lab and just drawing quietly together. That was really sweet. 

These days, as you run through those four pillars, flavors, of leadership, the operational, managerial, I’m naturally drawn less to that.

I’m more drawn to the creative and now executive strategy stuff. I have to be really careful though, because with a team of this size, what I don’t want to do is the swoop and poop, where I’m over here doing my executive stuff, and then suddenly I come and mess with people.

You know, people do design reviews with me and I give feedback. And the feedback that I try to give is typically not as much around fit and finish. It’s more around, “Oh, they’re not aware that there’s this whole other thing happening with product over here. But if they were able to find a way to weave that together, we could do more with what they’re working on right now. So let me make sure that they’re aware of that they have the right connections, they’re having the right conversations.” 

It’s sort of like being a cross-pollinator, being a bridge, doing that organizational wayfinding and having the super high-level context for what’s happening and bringing that into the detailed-level design work.

Where I do get involved, I do try to be kind of unapologetically opinionated about anything we design that’s gonna be for the end-user. So we’re a B-to-B company. We sell into the enterprise and we have a couple of key personas and one is like an IT administrator who’s going to deploy and manage Duo, but then he’s going to deploy as a company, and all of his employees have to use Duo as a two-factor authentication device to login to their work. So that’s sort of like the B to B to C in a way, like we are designing for the consumer. We’re selling into the enterprise.

I have a background in consumer web, so I spend a lot of time bringing that consumer web lens to enterprise security, which is kind of cool. And my theory,  my belief, is, if we can make the end-user successful, and make that a really great, super friction-free, experience, the value builds up.

It makes the IT administrator successful. It makes the buyer successful. The Chief Information Security Officer successful. So what we’re trying to do is shape good security behaviors, it’s a gross term, but in the security space, they call it security, hygiene, you know, good, security hygiene make that end user successful.

And that’s where I spend a lot of my attention and time to make sure that’s right.

Peter: That sounds like a conscious choice that you’ve made in terms of where you’re devoting that creative energy.

Sally: Yeah. And part of it is because those people have not opted into Duo. Duo has been foisted upon them, and I’m thinking, too, that your first encounter with Duo might be as a part of onboarding into a brand new job, you know? So you’re so inundated with new stuff when you start a new job, and Duo is one of a couple dozen things that you get introduced to you on your first day of onboarding into a new job. So understanding that as a context, as opposed to the buyer or the IT administrator, who’s done the research, done a little bit of competitive analysis, and has decided to choose Duo to deploy at their company.

So I’m really focused on the person who didn’t opt into this experience and making it great for them.

Peter: You mentioned less interest in the more management and operational aspects of your role. In my experience, those are the things, though, that, you know, keep the engine humming, keep the lights on, and if they’re not attended to, the organization starts kind of falling apart. How have you accommodated your less interest in those functions?

Is that one of those things where you just occasionally suck it up and like, “Okay. Today is my operational day and I’m just gonna kind of power through that.” Or strategies have you adopted to make sure that that’s getting attended to.

Sally: Yeah, I think one is, I’ve just built the self-awareness that those just don’t tend to be things that give me energy. They deplete my energy, but I can do them. And then, finding great leaders and great people who I trust that I can delegate work to who tend to thrive doing that type of work.

Like, that’s the magic is when you find the peanut butter to your jelly, right? Like someone who’s like, “I love doing the ops stuff. That’s my jam. This is what gives me life.” And then it’s a win-win, you know, it’s like every time there’s taxes and I’m like, I can’t believe there’re CPAs and they love doing this.

It’s so great. What a gift to humanity, these people. But yeah, they exist, and finding people who are great, almost like when you hear about CEO/COO partnerships and like the role of the COO is so varied and it’s so much depends on essentially, like, the psychographic profile of the CEO. They need to create a whole greater than the sum of its parts.

Jesse: And this is part of why I always advise leaders to tune into what they need for themselves, rather than trying to model the structure of their leadership on what somebody else created for themselves. Because, you know, your strengths are different. The complements that are going to support you are going to be different. 

So one of the themes I feel like throughout this conversation, has been the need to continue to be flexible in the face of ongoing change. And as we’re winding up here, I am curious about what changes you see around the corner? Is there a process of change that you’re in the middle of right now that you’re looking forward to seeing through?

Sally: Hmm, that’s good. Yeah. I’m in a reflective place right now and I am reflecting quite a lot on… I’m so proud of the work that we’ve done as a team, as a company, I’m really proud of the value that we’re creating in the world. Honestly, it’s such a joy to deeply believe that if more people buy the stuff that we make, the Silicon Valley cliche is, like, “make the world a better place.” 

It really does. We help with election security. We help with critical infrastructure. We help the trains run on time. It’s that part that is so cool. And I’m so proud that a design team can have positive impacts on the safety and trust that people feel when they use the internet. Like that is so cool. 

Earlier this year, before the pandemic set in, I was pushing myself to explore what it means to savor. And that was, like, a new thing for me. I’m feeling proud, I’m still working, I’m not disengaging from the work, but what does it mean to really savor a big accomplishment that I feel proud of? And, now I’m just reflecting forward on, What is the next chapter? I don’t know. It’s neat to talk to you all right now, because I do feel like I’m in a moment of trying to spend time to understand what that could and should mean for me.

Peter: You were referring to some of the societal context that we find ourselves in, and clearly this, this year has been a…

Sally: A Whopper. 

Peter: A difficult one. And I’m wondering how that has interceded into your and your team’s work lives, or do you try to keep a little wall around your team, and there’s work time and not-work time. Like, for eight hours, let’s focus on this and then, and then not, as opposed to, oftentimes, work and non work-life bleed together. How has that manifested within you and your team and how have you approached that?

Sally: I try to be really honest with what I’m struggling with right now, you know, so if I’m having a one-on-one conversation, I try to be really honest about what’s tough right now as an offer of vulnerability. If they feel the need to share, I want to make sure they feel like they can share with me in a way that’s safe.

I don’t want to dump on my team and create more stress for them, but I just want to show up as a real, fully-formed human, and, especially because the lines between personal and work life have blurred, if not completely dissolved for a lot of us, and then also trying to remember to bring some joy back. 

The thing I did yesterday morning was I spent some time over the weekend playing with gouache, and I hadn’t done that in quite awhile. It’s like a more opaque, watercolor-type of paint. So, if you enjoy pushing color around on paper, gouache is a lot of fun, and I’m just playing with it and getting to know it.

And so I just posted that on our team Slack Monday morning, just to remind them, we’re all creative people, and what are you doing to maintain your own creative practice? I try to share a bit of my personal life just to give them permission, if this is something that you would find to be restorative, even in the middle of your workday, giving them permission to do it.

When we’re not having fires, if I step away for a 10-minute walk, I’ll post that to the group Slack and say, “Hey, I just need to take a bit to recharge. And I’m going to go for a little walk.” And it’s not important that they know I’m walking. It’s more about modeling and give them permission to do what they need to do to take care of themselves too.

‘Cause that’s so important to me. One of the joys of leadership is getting to have these long-term form relationships with folks that extend beyond the time that you spend managing them. What a joy it is to see someone in the first few years of their career, and then even after they leave your company, getting to see what they do, and they check in with you, and seeing where they go from there.

Peter: I think that was a remarkably, positive, affirming note to wrap this discussion on, so, at least for me, thank you, Sally. Thank you for taking the time. It was great having you and I don’t want to speak for Jesse.

I actually, because I actually have to bounce. 

Jesse: (joking) I had a terrible time.

Fantastic. Thank you so much. This has been wonderful. 

Peter: And that wraps up another episode of Finding Our Way. As always, you can find Jesse and I on Twitter. I’m @peterme he’s @jjg. You can also find us on our website, http://findingourway.design/, where you can find past episodes with complete transcripts, as well as a contact form. We read everything that comes through there. It’s a great place to send any comments or questions that you have about the show, anything you’d like to hear us talk about in future episodes and with that, thank you for your attention and as always keep on finding your way.

In which Jesse and Peter dig into a few emerging trends we’ve seen in product design teams, including the rise of the senior individual contributor, the increasingly tangled relationship between design, engineering, and product management, and what it takes to lay the foundation for lasting change.

Peter: Oh, shit. Design leaders are spending all their time managing and recruiting and hiring and, caring and nurturing for their teams, but they’re not spending any of their time leading design.

Peter: I’m Peter Merholz,

Jesse: And I am Jesse James Garrett…

Together: …and we are Finding Our Way…

Peter: …Navigating the challenges and opportunities of design and design leadership.   

Jesse: On today’s show Peter and I dig into a few emerging trends we’ve seen in product design teams, including the rise of the senior individual contributor, the increasingly tangled relationship between design, engineering, and product management, and what it takes to lay the foundation for lasting change.

Peter: One of the things that I think is interesting that I’ve seen more of during our break is a legit establishment of this design leadership role that doesn’t assume management.  So, one of the companies I’m working for, a big bank, is hiring up to 20 people who are true senior design leaders. They would be senior manager or director level, but with no expectation of management and direct reports. They are organizational leaders, they are creative leaders, they are strategic leaders. They are there in large part because those folks who do manage are so overwhelmed with their relationship responsibilities, that they need support from folks who can focus on the work.

I’m seeing it more and more, and I’m hearing from other design leaders that I’m talking to a desire to establish that role within their organizations. It’s almost like, wait, can we do that? We can have someone who’s really senior, but not manages people? Will they allow that to happen? And it’s like, yeah, if you want it.

Jesse: Well, it depends on where you are, and it depends on cultural context that you’re in because, in a lot of cases, one of the challenges with the senior individual contributor is, How do you measure the impact that they’re having beyond the work that they’re delivering? How do you measure the leadership dimension of what that person does so that the organization can know if they’ve got the right people in those senior roles?

Peter: How would you measure that if they had direct reports?

Jesse: Well, if they had direct reports, then you’ve got a broader set of data to consider in terms of the contribution that the individual is making and the success that they’re finding in the organization. It becomes about team cohesion, team success, team delivery kinds of metrics.

Peter: You measure these senior IC leaders similarly, it’s just the team doesn’t report to them. So way this is structured, and I think this is why we’re starting to see this more and more, management is functional, you’ll have design managers managing designers, and design directors managing design managers, and often not just functional within design, but like research managers managing researchers, and content strategy managers managing content strategists. This individual contributor design leadership role is a principal designer role, and s leading a team that is cross-functional within design. So there will be product designers, researchers, content strategists. 

So it’s around leading the work, not leading, not managing the resource to put it another way. And then additionally, as they get more senior, they’re very active in leading cross-functionally. So they’re not necessarily directing product people and engineers, but definitely influencing them.

And in terms of accountability, these folks are ultimately held accountable for the output of the teams that they are directing.

Jesse: So tell me about how formal authority works in these situations because what happens generally is that authority tends to hew pretty closely to reporting structures.

Peter: You’re seeing that less and less, I think, in these product development organizations where reporting is functional, but delivery is cross-functional. This is becoming an accepted just way of being. So a design director has less creative authority than the design lead within a cross functional team often, right, because the design lead in a cross functional team, working with the product manager and engineer, is making the design decisions at that level of delivery. And that is where the authority thus resides.

Jesse: Yeah. If you don’t have the ability to actively direct the work of a designer, if it is, as you describe, influence, then how do you assess how much influence you have had?

Peter: It depends on where you locate creative authority within these structures. So you can imagine at the simplest level, you have two structures: you have your reporting structure of design and engineering and product reporting up through their functions; and then you have the work structure, which is cross-functional teams. Think of that as squads, pods, whatever, where you have a mix of product managers, designers, engineers, working together. 

Now in some organizations, they are using that work structure as the management structure. But I’m frankly seeing that less and less. What I’m seeing more and more of is a recognition that we should organize reporting structures by function, because there’s value there: Professional development, recruiting and hiring, there’s value in making it clear how you grow within your function. 

But the work is being organized in these cross functional teams, which have their own structure. 

When I’ve worked in marketplace models, you’ll have a team dedicated to the sell side of the marketplace and a team dedicated to the buy side of the marketplace. and those become these work structures. And so the creative authority resides on the work side, not on the reporting side.

Design directors aren’t coming over necessarily to the work side. They are seen primarily as organizational minders, because there’s plenty of work to do recruiting and hiring, professional development, and one-on-ones, and all that kind of stuff. 

But you still need creative leaders. There can be a different authority structure specific to the work from a reporting structure. And so these super-senior ICs might report to a design director, but they lead a set of work in the work structure.

Jesse: Who looks after design as a practice in this model?

Peter: Oftentimes those leaders will also be practice leads. 

So you’ll have your content strategists or UX writers reporting to a manager of content strategy, possibly reporting to a director of content strategy. Director and manager of content strategy own the practice and the reporting relationships. The issue that arises is: I’m a director of product design. And I have product design leads, who report to me who are in the workstream leading work.

They are the creative authority for work in their area. What is my job as a creative authority as a director of product design?

And my take on it is that the practice leads—director of product design, director of content strategy, director of user research—they establish a framework for quality. So they create the shared understanding of what quality is. The people doing the work are then expected to deliver at those levels of quality.

Jesse: And who evaluates that?

Peter: So evaluation becomes an interesting question, because in my worldview, and this goes back to our work at Adaptive Path, that creative lead needs to be the sole authority over what gets launched. 

That director of product design might look at what that lead product designer’s putting out there and saying, “That’s not living up to our quality standards.” There’s a disjuncture here. In the moment, the director of product design, and unless it is truly egregious and they want to pull the emergency cord, doesn’t really have the authority to stop that work in the construct that I’m putting out there. If the lead in the moment is like, “No, this is what solving the problem. We’re going to launch it.” 

Then, if there is a disconnect between an established understanding of quality and what is actually getting shipped under a particular lead product designer, Then there’s a conversation about what’s going on there. Often, what you find going on there is that there are a lot of conditions within that cross-functional team that inhibit that designer’s ability to deliver at the level of quality that the practice lead has established. So then it becomes this other challenge of, “Do we need to encourage new organizational practices to enable us to achieve the level of quality that we are establishing?”

Jesse: Right, right. This is a thing that I’ve seen organizations struggle with figuring out, where that line is, how involved the senior most leader is in looking at the details of the creative work being produced by the leads underneath them.

And how do they influence practice and process based on that, because a lot of what you’re talking about is stuff that emerges out of the negotiations across a cross-functional team, as they are figuring out how to balance all the considerations in order to deliver. This role, as you’re describing it, that has responsibility for those practices and processes is also pretty far removed from them, and is also really just kind of seeing things after the fact. What I’ve seen is that that loop never gets closed. Energy and attention of the senior-most leader is so focused on things like budget and resources and things like that, that they don’t have the space to be able to actually take stewardship, take ownership of design as a practice in these organizations.

Peter: That is definitely an issue, especially as these organizations scale. 

But, that’s where Design Operations plays a part. 

I was actually just talking with one of the heads of product design that I work with. He has a team 80 or so, and he’s been able to get himself, right now and for the next month or so, where two days a week he’s doing what you would expect a design leader to do: going to meetings, one-on-ones, recruiting, hiring, that kind of stuff. 

The other three days a week, he’s working with a small team, small cross-functional team, on building out a vision, a product vision, a North-Star type work for the company. And he recognizes it’s temporary, right? It’s time boxed. This couldn’t be his job forever because he does need to get back to it. But he’s able, for a while, to only do two days a week doing what people consider his job-job. So he can spend three days a week being the creative leader that no one else can be in this organization.

And one of the reasons he can do it is he delegated all of his budgetary activity to his head of design ops. Just, like, “You own it. You do it. If you need me to check in, provide direction, give you guidance, whatever, happy to. It’s my org, so I care about this stuff, but literally you are going to all those meetings with the finance people. You are in charge of that now.” 

And so I think we don’t do enough to decompose the responsibilities of design leaders, and really recognize all the things that they need to be doing, and, What are those things that really the design leadership should be focused on? And what are the things that they can delegate or put off their plate? 

That’s why DesignOps is emerging, is this recognition that design leaders were spending all their time operating and none of their time leading design. But now this other thing is happening is, “Okay. So we’re delegating design operations, oh, shit, design leaders are spending all their time managing and recruiting and hiring and caring and nurturing for their teams, but they’re not spending any of their time leading design. So how do we shift those activities and responsibilities among a set of leaders so that everyone can deliver well on some aspect of this, instead of one person, half-assing a whole bunch of things.

Jesse: Right. Right.

Peter: And I hear you in terms of we’re not caught up there. And so loops don’t get closed. People are far away from the work and that’s still a problem to solve.

Jesse: It takes a village to lead design, right?

Peter: Essentially. Yeah. And I think we recognized this 20 years ago in engineering, you’ve had a VP role of engineering, which tended to be the org minder. You had your CTO or architect roles that tended to be what we would consider creative leads or technology leads, the ones figuring out how to solve the problems, the technical problems.

So there was that bifurcation happened a long time ago. You had technical program management, is this other function that was then essentially there to support engineering. With the agile revolution, you have agile coaches and scrum masters and all these other people figuring out how to keep the work engine humming.

So there had already been this recognition of all these different things that need to get done and a decomposition of activities across roles to enable that to get done, and design is just behind. ‘Cause it’s taken us longer to get to a similar scale. 

Music break 1

Jesse: Part of this really has to do with the culture of leadership within the larger organization that you’re a part of, especially how collaborative, how consensus-driven, how consultative the decision-making culture of the organization is, because in an organization that broadly asks its leaders to take a more command-and-control kind of stance, approaching leadership in this way can be really challenging, because even if it feels, to the design leader, like there is a better way to do this, that is more hands off, that distributes power and authority at a lower level in the organization more effectively, they may be contending with a larger culture that looks at what they’re doing, and it looks to them like they’re fucking it up because they’re not leading according to the model that the rest of the entire organization, including the CEO, potentially leads.

Peter: Totally. What’s interesting to me– the problem I’ve seen is actually the inverse, where the cultural direction was more bottom-up. It was autonomous product teams. Do whatever you want. The output is crappy, for any number of reasons: it’s not coordinated across these teams, plus there’s not a shared understanding of what quality looks like. And, in this one instance when leadership would review the work of these teams and say, “It’s not good enough, don’t ship it,” these teams would ship it anyway. And there was no accountability.

There was no… 

Jesse: …that loop closing. Yeah. Right. 

Peter: Some organizations could stand to have a little more top-down, command-and-control, to drive quality. 

What’s happened in this organization, is they’re at some stage in their cycle where they need a shock to the system to improve quality, and that shock is not going to come from the bottom-up. It’s too fractured. The amount of effort it would take to kind of dial up all these individual teams would be too great. 

But one of the benefits of hierarchies, when you can wield them appropriately, is to do a hopefully positive shock from the top-down and say, “No, that’s not appropriate. Here’s some new standards of quality. And if your work is not measuring up to these handed-down standards of quality, then it is not shipping,  and we need to take this approach because the problem is so severe that we need to almost explicitly work in a way that we don’t want to work, work to overcome this issue in an effort to reset.”

Try to get a new normal understood within the organization so that after you do this top-down, command-and-control for a while, there’s the understanding, the awareness, the appreciation of that built so that you can then pull back and have some faith that the teams will continue to deliver it, that new level of quality. 

So I, I almost, I long for command and control. Which goes against my, a lot of my philosophy as I was saying earlier, the authority has to be given to the person who has accountability for delivery. And that’s usually someone at that level of a product team, shipping stuff.

Jesse: So, typically, that locus of power either resides with the creative lead for the particular piece of work as you’re describing, or the person who is that person’s manager, that person’s performance manager. And this third element that you’re talking about, this senior-level individual contributor without

performance management responsibilities,feels like this extra thing in these organizations that they’re trying to figure out. How this third center of authority fits in with these other two. And organizations are struggling to give it teeth because the larger organizations are looking at design teams alongside their technology teams and the various other teams that are responsible for delivering all of the functions of the business, and trying to figure out how to make the design team look more like their other teams as much as they can, to simplify their management of a complex cross-functional ecosystem.

Peter: In the case of this one company, they have an engineering team that actually is serving as a positive model. 

What I’m sensing based on this conversation is what we’re all part of, is there is a shift occurring from whatever was standard, let’s say 20 years ago, that I think was much more like you were saying: a lot more command-and-control, the reporting organization was also the delivery organization. Your manager was responsible for your performance and your output, and their manager was responsible, and, and it was cleaner in some way.

And then what happened essentially, is this recognition of, in the 21st century, to succeed in doing work requires cross-functional teams. You cannot go inside an organization that doesn’t recognize the importance of a truly cross-functional team. We’re talking design and engineering and product management and data science and marketing, like true cross-functional teams. And the model before was you didn’t collaborate cross-functionally, you did your work and then you handed it off to the next function, and you handed it off to the next function. And so that, it’s not even waterfall model so much as this kind of yeah, the production line model.

It doesn’t work when you’re trying to be nimble, responsive. When you’re working in a world of software as a service and, you’re constantly shipping and all that kind of stuff. And so they’ve moved to this cross-functional team where you have representatives of those functions present at all times.

We still don’t quite know how to manage complex cross-functional delivery. We know how to manage functional organizations. Certain aspects are still being managed functionally—your professional development and, and your, performance reviews and the skills growth and all that kind of stuff

We don’t have clear, well-understood models of how you manage cross functional teams, particularly at scale. 

To take what you said moving forward: I just think we’re not there yet. There is not an answer. We’re still figuring it out.

And what I think we’re seeing is that issue, the challenge, conflict, that soreness that is happening with design leaders is because we’re trying to manage cross-functional work teams akin to how we managed perhaps in the past, these hierarchical teams and it’s not quite working.

And so now we’re trying, let’s go the other direction and it’s all autonomous and every team’s on its own and that’s not working. And we’re stumbling toward what is a model that allows functions to work well together as teams at scale. And no one has really solved that in a clear, repeatable way that people can feel pretty good about.

Jesse: It’s interesting that you keep referring back to development methodologies, in that I think that for most of my career, if not all of my career, the conventional wisdom among designers would have been that you should not attempt to manage design the way that you manage engineering, that engineering management practices are too factory floor production line oriented.

They don’t have enough flex or space in them for the creative exploration that’s necessary for design. That design as a practice was fundamentally incompatible with the way that technical development gets managed. And it feels like you’re saying that if that was true, that maybe is not as true anymore, or even perhaps that the folks who have been doing this work to define these approaches to technical development have lapped us basically, and gotten out in front on these issues of how to get multiple functions actually integrated together effectively, which is really different from, frankly, most of what I’ve heard from most designers for most of my career.

Peter: So they’ve lapped us. I wouldn’t say that they’ve solved it though. If you ever hear of a designer embedded in a product team, squad, scrum, et cetera, that is a model created for engineering delivery. And, it is not a model that leads to good design, but they got out in front of us.

They’ve been dealing with these problems longer because engineering orgs tend to be bigger. The value of engineering was more evident to internal leaders. And so they built out engineering orgs sooner.  But these, what are meant to be cross-functional, organizational frameworks definitely skewed towards  supporting engineering over the other functions. That’s actually one of the reasons we wrote the book, was I saw this occurring and I was frustrated because you are right. Design works best in its own way, not by adopting engineering processes. But when design got subsumed into these, what were supposed to be cross-functional, team structures, that were really about how do we help engineering be as effective as it can be, and to heck with anyone else,   design suffered in that regard.

People often forget that much of what we think of as agile is simply a way for engineers to to assert the authority over their work, because it had gotten away from them. They were being told by managers, who didn’t actually understand what it took to deliver, what to do. And the engineers were like, no, we’re taking the reins back. Right? It was their own form of, frankly, a kind of quasi-Marxist maneuver. What’s happened, though, is designers haven’t yet done that themselves. Designers haven’t taken those reins.

Music break 2

Jesse: All of this makes me very curious about the work that was done by technology leaders, you know, 15 years ago to start pushing the

process and organizational change in these organizations, away from the way that software had traditionally been made up to that point. And how they were able to make the argument for such a radically different style to their leadership.  Because, frankly, that is one of the things that we as designers and as design leaders have had the hardest time doing, is simply convincing our leaders that there is a different way to do things and we should be given the permission to try.

Peter: Part of their ability to make that change is the phrase, “Double the work in half the time.” And what CEO isn’t going to like pause for a second. 

Jesse: “Tell me more,” 

Peter: “Yeah. I want some of that.” 

I think the challenge, I hadn’t thought about it this way, but it kind of goes back to what you were saying about the difference earlier, but just between engineering practices and design practices, engineering is measured on productivity and how they define quality, which is uptime, no bugs, stability, performance. All very mechanized outputs. 

Engineering is not held accountable for business success. Engineering is not held accountable for customer engagement. Engineering is not held accountable for all those fuzzier, squishier impacts on users and customers. Engineering is held accountable for, Are our machines able to do what we want the machines to do?

If all you want from design is more design, then, yes, you can put design in a similar context and you will get more design, but that’s, yeah, it’s laughable ‘cause it’s meaningless and, there’s just this fundamental difference in the paradigm of what the value is that design delivers and the value is that engineering delivers.

Jesse: And I think it comes back to how that value is communicated to and understood by the senior business leadership.

Peter: I thought tou were going to say, “Senior bean counters.”

Jesse: That, yes, those, too. So, as you describe the agile transformation, it sounds like those people were able to speak to value in a way that their nontechnical leaders could understand, right? You didn’t have to understand the ins and outs of technical development processes in order to be able to understand the value of “double the work in half the time.”

And we don’t even have ways to talk about the value that we’re delivering now, nevermind talking about increasing that value in the future. They already had a reference point for engineering when agile came onto the scene. They had ways of evaluating. They were maybe not the best ways, but they had ways of evaluating that were needles that they could see would be moved by a move to a different approach.

And they don’t have that for us. They don’t have needles that they can look at and go, well, this, and this, and this will obviously change if this works the way that you guys say it will.

Peter: They do and they don’t. Unfortunately the needles they have for us are productivity needles. That’s why I think much of design as it has scaled has also been reduced to output. My question or my, my wonderment based on what you’re saying is, nor do they have metrics to justify more product management, but they invest in it.

Jesse: Okay. So what’s that about?

Peter: That’s a good question. I think about this.. I found myself thinking about it again more recently. I find myself wondering why companies keep hiring product managers. They love hiring product managers, but what ends up happening is from a ratio standpoint, you get these ratios out of whack, where you get multiple product managers for a single designer.

And I’m like, “Why do companies keep hiring product managers when they don’t have the team to deliver what the product manager is working on?” And I think the reason they keep hiring product managers is that product management is a promise of future value. 

Jesse: And design is not even that, is it?

Peter: It’s not recognized as that. We know it is, but it’s not recognized as that. So, by hiring a product manager, you believe you are enabling the ability to deliver more product, new product. And with that delivery of more, a new product, the generation of increased value. So, you hire product managers because for every product manager, we can launch another feature and another feature.

For some reason, what’s not fully understood or appreciated is when you have product managers, the job of a product manager is to make work for other people.

Jesse: Hmm.

Peter: And so you have all these product managers generating work, but if you’re not also hiring engineers and designers and others at a similar clip, what ends up happening is, and I’ve seen this, I’ve been in environments where product managers almost literally are walking the halls with requirements, looking for someone to execute on them, just like, “Do you have time? Can you, can you help me build this thing?”

And now everybody else is somehow pulled into this person’s insanity. It leads to all these problems. That said, thinking about what you were saying in terms of design and the ability to cleanly and clearly value design, design’s value is

essentially the same as product management value. When you want to look at it from a business lens, designers help you with acquiring new customers, help you with retaining customers, help you engage customers, help you potentially get those customers to spend more while they are engaged. So, you know, unlocking more revenue or whatever, right?

Those are all metrics that a business cares about. That doesn’t take a lot of imagination to connect a designer’s work to those metrics. Those metrics though, tend to be owned by product, but product doesn’t actually deliver on those metrics or do anything to make those metrics happen.

Usually they rely on their teams. And their job is to coordinate the efforts of those teams towards those business goals. As we said, though, the engineers, their metrics aren’t really product metrics. Engineers’ metrics are engineering metrics with this assumption that, I guess, a magic in the system, that if the engineers focusing on their metrics keep machines running and product is focusing on their metrics and value creation, then it’ll all work out. 

Now, this is a thought I hadn’t had before. And I think that the hidden connection that hadn’t been realized was the designer is the person who turns that engineering quality into value realized by the product manager.

Jesse: And is cut out of the equation altogether themselves.

It feels like there is, is a lack of things for designers to uniquely own that have value beyond the aesthetic, beyond the subjective.

Peter: That is basically true. There is no meaningful design metric that isn’t also a product metric.

You’re making me want to look up a tweet. Hopefully it won’t take long. 

On February 23rd, 2020, Jared Spool wrote, “I’m of the belief that in a few years, product management and UX design leadership will be indistinguishable. In some orgs they already are.”  And that, I think, speaks to what we’re talking about. 

Jesse: Yeah. I think most of the time, if you look at two different functions in the organization and they are impacting the same metrics, that seems like a pretty good argument that those functions should be combined in some way. You know, maybe design is an adjunct to product management, maybe there is a space for a design practice that is more fully integrated with product management as a way of sort of borrowing that understanding of value and being able to transfer that to the design work. Should designers be reporting to product managers?

Peter: Product managers. Hmmm, no. At least not the way that it is typically practiced in most organizations. I think this is another area, as the tweet suggests, we’re seeing change and evolution. 

There’s no reason that that product manager can’t be a designer or could not have once been aa designer. And we’re seeing that all throughout the industry, more and more designers are turning into product managers. It’s still the vast minority, but we’re seeing a greater and greater acceptance of designer as product manager, as opposed to historically it was MBA as product manager or

engineering lead as product manager. We’re now seeing companies realize like, oh, the product is this thing that people use. Maybe the person who’s managing the product should have a ability to understand that use.

Jesse: I have been advocating for at least 10 years now that designers who actually want more authority, want more power, need to move toward product management. They can do product management from a design sort of stance. I don’t think it means leaving behind that creative influence. And in fact, I feel like there is something missing in the practice of product management, as I’ve seen it, that designers bring, which is this holistic experiential sense. That is not something that I’ve seen a part of how product managers do their jobs. 

Peter: Right. No, that’s and, that is, I think, largely true. It is changing, but still largely true. It was probably about 15 years ago that you created a talk called The Experience is the Product. Which I don’t think we realized at the time what we were saying. Organizationally, we were just commenting on what we saw in the world, and that instead of focusing on products as these one-offs, we wanted to encourage people to think about a broader experience context in which these products sat. 

I have a 2020 version of that talk still called The Experience is the Product, which makes much more explicit that connection between user experience of the word experience, and product management of the word product and that user experience and product management are essentially the same thing.

Music Break 

Peter: One of the companies I’m working with has come to a realization that the quality of the product that they are delivering is subpar. A few years ago, they brought on a very senior design leader who came in, was given a mandate, looked around, was like, “This isn’t great. I gotta do a lot of stuff. I got to fix this,” and wasn’t able to get traction. Wasn’t able to make kind of change happen that they realized needed to happen. And three years later, this team is still producing crap. As I started digging around, I found out that there had also been, within the last couple of years, a new head of product management and a new head of product marketing hired, who similarly came in, looked around, said, “Oh, I gotta make some changes.” And realized much greater success in making changes in their part of the organization. 

So, my initial concern was that it was some type of broadly cultural thing, but no, this new head of product was able to do a real reorg, make some real changes. Their new head of product marketing basically changed how they do product marketing, like the processes by which they operated. And I was like, “Why is it that this new senior design leader wasn’t able to realize their vision, the way that this person’s peers did?” And as I unpacked it, I found out that this new design leader, their leaders didn’t have their back the same way that the product management and product marketing leaders basically ran cover for these new leaders that they brought in. 

So when the new product leader or the new product marketing leader is making these changes and ruffling feathers and pissing people off, and the message is going back to their boss, “What’s what’s going on here? So, and so’s doing all this stuff. This is new, it’s different. It’s not right.” Those leaders were like, “You know what? That person’s in charge. If this is what they think needs to happen,  they have my full support.” in this design context, when that happened, those super senior design leaders told this new design leader, “Hey, Hey, you need to back off a bit. You’re upsetting people. You’re not doing it the way we work here.” 

And what it pointed out to me is, however senior you are as a leader, you need another leader to support you in the change that you are trying to make.

We tend to think that leaders are almost operating on an island or like if they have a strong enough vision they can just carry people forward. 

And in reality, leaders need leaders to protect and cover and enable and support them. And it’s not something I had been as cognizant of, until seeing this side-by-side compare-and-contrast of a leader who’s been given that cover and the change they were able to make, and a leader not given that cover and them getting stonewalled.

And now years later, I’m hearing that this leader maybe isn’t delivering up to what would be expected. And it’s like, “Yeah, because they weren’t given the support they needed when, they were like, ‘Hey, we should do these things.’”

Jesse: You didn’t let them optimize the environment for their own success… 

Peter: Yeah, yeah…

Jesse: …so don’t be surprised when they’re not successful. Yeah. Yeah. And, this goes back a little bit to what we were talking about a few minutes ago, about the early days of agile and how those folks made the case for that change in those organizations.

And it did eventually take somebody up top who didn’t understand the deeper implications, who didn’t understand the reasons for all of the changes, say, “I don’t care that I don’t understand it. I believe in you. And I believe in what you’re doing and I believe you’re the right person to orchestrate this.”

And that I think is a level of credibility and trust that engineering leaders had circa 2005 as they were starting to push agile as process change, as cultural change, in these organizations, that designers haven’t gotten to yet. And in fact, product managers have stepped in and they’ve already got more power than we’ve got and they just showed up.

Peter: Yeah, I think it ties back to what we talked quite a while ago about trust and about relationships. And I think a lot of design leaders don’t know how important it is to manage up and manage those relationships well, in order to then manage down to get what you want.

They come in, look around, they see the problem. They feel it must be evident to everybody and they start trying to make change and it tends to be out and down. ‘Cause that’s where they’re seeing problems are. And they haven’t done the work to manage up, to play the politics, to get the relationships, to get the connections, to get the cover so that when they then do manage down, it’s going to ruffle feathers, right? Change, upsets people. So you need to have prepared yourself and others for that disruption and seeded the ground appropriately to make sure that when there’s the hue and cry about change, you are enabled to continue that change.

Not encouraged to just roll it back.

Jesse: And I think it’s on the design leader as well to accurately assess the organization’s true appetite for disruption. 

Peter: Appetite for disruption! 

Jesse: Our new album. 

By the way, you have to know that your leadership is already on board with the chaos that’s going to come with change before you start trying to make it, because if you start trying to make that change when you’re not sure if your boss wants it or is ready for it… I mean, we ran into this over and over again, as consultants at Adaptive Path, where would come into organizations, we would be working directly with a client who was very motivated to create change, had gotten the budget to bring us in and had spun up a whole bunch of work around creating that change. But had not accurately assessed their leadership’s appetite for it. And the work ended up dead in the water as a result.

Peter: Totally. Totally. Yeah. and while it would be easy to point fingers at the super senior leaders for not providing the cover for this new leader to realize the changes they wanted, I did also realize that this new leader hadn’t done their diligence in making sure they’d had the relationships established.

They had gotten very problem-focused and “I’m just going to solve the problem,” which designers do and had lost sight of the people parts around that. 

Jesse: And this is really what was behind my pivot toward leadership coaching,  helping individuals maintain that level of awareness and that level of engagement beyond the tactics of delivery, toward: look around the room, who are the people in the room and how are you engaging with them? Because it’s very easy to think that these problems can be solved with more process when actually what you need to be doing is having conversations with people. 

Jesse: Well that wraps up another episode of Finding Our Way. Thanks, Peter.  

Peter: Thank you, Jesse. 

Jesse: He’s @peterme. I’m @jjg.  

Peter: You can find us on our website at http://findingourway.design/, where you can also find past episodes and complete transcripts of every episode, as well as a contact page where you can send us your thoughts. We read everything that comes through, and those submissions have often spurred further discussions.

Jesse: Thanks, Peter. 

Peter: Thanks, Jesse.

Peter: Me me, me, me, me… Do you have a top knot or back knot or something?

Jesse: I have a, I have a high pony.

Peter: Is that what it’s called?

Jesse: That’s what I’m calling it.

Peter: So you have a pony that is high.

Jesse: Yes. Yes.

Peter: It’s those Oakland oats.

Jesse: It’s, it’s wandering around my backyard. Just sort of like eating everything.

In which Jesse and Peter answer questions on funding models, shifting from output to impact, demonstrating value, and the challenges of being a design leader right now.

Questions addressed:

(01:00) “How does a good business fund design activity?”

(09:28) “How can one handle being a good lead designer, when in the company where you work, the majority of product owners don’t understand their role.”

(12:43) “[How can] design influence their orgs to move from an artifact/output-based model of design to a practice/impact one?”

(16:40) “How [can] a design team better frame their unique value inside an organization that is crowded out by engineering voices and investment. How can I articulate the value that the design team creates as being as critical as sound software engineering?”

(26:34) “How can I help my team feel secure and supported when my own world is adrift on stormy seas,” and “How to help my designers feel safe and secure in rocky times.”

Peter: Welcome to Finding Our Way, the podcast where Peter and Jesse invite you on their journey as they navigate the challenges and opportunities of design and design leadership. I’m Peter Merholz. And, as always, with me is Jesse James Garrett. 

Jesse: Hello Peter.

Peter: Hi, Jesse. So today as we enter a kind of summer hiatus, we thought we would take questions from listeners. We polled listeners across Twitter and LinkedIn and got a number of questions. 

To start, thanks to everybody who offered a question, we read them all.

We won’t be able to get to them all. 

There were a set of questions that came in that were essentially around the idea of how to value design

Lar Veale on Twitter asks us: “How does a good business fund design activity?”

Jesse: Where does the money come from?

Peter: This is one of those topics that when I think about understanding what’s really going on behind the scenes, one of those moments for design leaders, at least for some design leaders, is when they realize that finance runs everything.  

Those design leaders have never been equipped to handle that conversation, but the budgets that they get, the headcount that they get, the resources that they get, all of that gets reduced to money. And that money is controlled by those folks over there in finance and in order for design to succeed, the design leader now needs to figure out how to bridge with finance.

Jesse: Right. A whole new audience, a whole new language, a whole different set of things than the leader has ever had to engage with as a designer, most likely.

Peter: When I read this question, I actually thought about a company that we are both familiar with. The funding model was an interesting one. They have a massive centralized product design team.

And the funding for those designers comes from the different lines of business. And so even though the team is managed centrally, the money is contributed, essentially, in a decentralized fashion. And it led to what I considered to be the existential crisis of the design organization, which is a lack of control over how many people they hired and what they had those people work on, because a design leader needs to be able to make a decision around what are people working on, based on the priorities of the business as they understand it.

But if your funding presupposes your headcount, you have now had a key lever of your decision making taken away from you. And then that further puts you in a subservient relationship to that line of business, because you’re basically their work for hire.

Jesse: That’s an interesting take, because it suggests that if you can’t get close to the sources of funding, if you can’t get in a position of power around your funding, you’re never going to have the strategic influence as a design organization that you want to have, is that true?

Peter: I think that’s true. But my ideal world is… Let’s say taking that example where you have different lines of business who all recognize that they need design. Instead of enabling this kind of transactional relationship between that line of business and design, now all those lines of business, somewhat blindly, maybe based on a percentage of their revenue, or percentage of their effort, or some algorithm separate from all of this, that line of business basically pays a tax to the centralized design function. And that goes into a big pool of money that is managed by this design function.

The design team, then looking across the entire business, identifies what matters, what’s important, what are we going to act against, and figures out how to shape its teams and resources to deliver on what the whole business has deemed important.

One of the things that you get with this, that is hard to do when you’re working in this transactional relationship, to answer your other point around being able to make a strategic impact, is that ability to work across the lines of business.

Jesse: You know, I do think that there is a concrete value for businesses in having those purse strings controlled by product owners rather than by design organizations, because those are the people who are currently engaged at that peer level with each other to do that strategic coordination across your product lines.

Unless you’re going to invest design with that responsibility, which really means in some ways elevating design above product management, you’re not going to get there. And so I’m curious about how you do get there. 

So the question is, How does a good business fund design activity? What’s the best funding model for design that you’ve seen in your experience?

Peter: The best model is essentially tied to general company growth. When I was at Groupon, we didn’t have lines of business that funded me or whatever. We had an understanding of how we wanted to grow as an organization, and there was an appreciation of what was needed from a product development standpoint, not just design, but product managers, engineering, data analysis, dev ops, all that kind of stuff.

And design just kind of gets carried along with that growth. Now that ends up leading to ratios often, which is a heuristic for design funding. So if we’re going to hire eight engineers, we’re going to hire one designer. That kind of thing. And those ratios, I’m not against, but I’m not a huge fan of. I find that they are a proxy for understanding growth.

What I’ve tried to do is, when you’re engaged in these headcount planning points in the second half of the year, you’re doing the planning for the next year and you understand what the strategic direction is, and thus what all the programs are. I then plan my designers against those programs, regardless of what other decisions are being made. If we’re going to engage in these five programs of work, well, I’m going to need 10 designers, roughly two per program. And that’s what I asked for. 

What I’ve also learned is you always have to ask for twice as many resources as you actually think you need. 

Jesse: The secret ratio.

Peter: Yeah, well, you know, it’s negotiation. 

When you start operating in these funding models, typical for any large enterprise, you’ve probably already lost the plot, because those funding models end up becoming very transactional and it doesn’t only affect design. 

So you were talking about product management and others. What you’re starting to see is… lines of business. You have your line of business over there. And they’re responsible for P and L of a different business. And then separate from those lines of businesses are technology services. And so these UX designers say are part of a technology service that includes development, engineering, product owners, QA, and dev ops and all that kind of stuff.

Jesse: So everything about product is construed as basically a service organization to the business.

Peter: Exactly. These product development organizations, say they embrace agile at scale, maybe Scaled Agile. 

The problem is baked into agile, baked into scrum. It assumes that that team has autonomy. But if that team is really in service to the line of business, they don’t have autonomy. They’re getting their requirements from outside of their bubble, from people who don’t actually understand what’s happening, but just have these expectations and that really puts the product owner in a difficult position. 

This is one of those challenges, I think, product owners or product managers face that designers often don’t respect or understand—is how much of the decision making has been done before the product owner even starts their work. And they’re just expected to execute on a set of requirements that have been handed to them. One of my clients has been operating in this way and they’re starting to take people from the line of business and make them the product owners.

You know, that’s one of those key distinctions between quote unquote tech, companies, your FAANG companies, and your legacy firms. In tech, those product owners, those product managers are the business there. It’s not a distinction between a line of business and a product.  

In these legacy enterprises, you have lines of business and tech as these distinct entities within the business. And once you have that, you’ve basically already lost it. You’re done. You might as well go back to waterfall. 

Jesse: Wow. that’s I think a bold statement. It’s interesting that you mentioned this just because we actually have an email here that is related to this, coincidentally.

Marina writes in via email, “How can one handle being a good lead designer, when in the company where you work, the majority of product owners don’t understand their role? They are merely order takers for a higher level of the company.” 

And that’s exactly what you’re talking about. She’s sharing the frustration of being in the lead designer role and having to be the person who is chasing down the true meaning behind the requirements that they’re being handed, where the product owners can’t articulate it for them, because it’s not a conversation that they’ve even had with the people in the business that they’re engaging with.

And so then it ends up falling, not on the lead designer, as much as it does on the design leader to reach out into those other parts of the business and start that engagement, but that’s challenging when, to your point about funding models, the funding model that you’ve been set up with creates a prejudice in people’s minds about the nature of the value that you deliver.

There are all kinds of assumptions about your value that are built into how you are funded. And so when you’re engaging with these new parts, these organizations, when you’re diving deeper into the business to have these conversations about the true meaning of these requirements, it’s really hard to engage them in these strategic conversations, when their perception of you is colored by this funding model that puts you in a purely tactical service-oriented role.

Peter: All of that is exactly right. To address Marina’s question, you know, these product owners, they may understand their role, they might be delivering their role. Their role is to execute on what the higher levels of the company have told them. So order-taking might be their role. 

Now, that’s not what we believe is what product owners should be doing, in an ideal context. But that might be what they are expected to be doing in that specific context. And so this is no longer a design and delivery problem.

This is a change management issue. You need to start working with your product peers and engineering peers and, developing arguments for why you should be working differently with those higher orders of the company. You need to help those higher orders of the company understand how they are constraining opportunity from square one with how they are behaving, and that if they want to realize greater potential, need to change how you all work together. 

So, it’s not a straightforward design problem. It is this organization, process-oriented change management problem, that’s going to be really hard, it’s not going to be straightforward. It’s a quick thing to say, and it will take years, it will take literally years to deliver.

Jesse: Yeah. Well, when framed that way, what I hear is a lot of politics and politics is a slow and messy business and anything that requires a lot of politics to bring about is not something that’s going to happen on a six-month timeline. It’s going to be 18 months to two years to lay the groundwork for that kind of change at that scale that you’re talking about.

Music break

Peter: I think we can connect this thread to another question, from Pavel Samsonov, who asks, “It’d be great to hear your thoughts on how designers can influence their orgs to move from an artifact/output-based model of design to a practice/impact-based one.”

When I was working with Capital One, many years ago, I ended up talking a little bit with Aradhana Goel, who developed an approach to trying to address this funding model, to make it less directly transactional—“I give you money. You give me heads.” And instead, because her background was consulting, she was able to draw on that consulting practice and say, “You’re not giving me money for heads. You’re giving me money for results. And here’s my commitment to you. I will deliver this kind of impact through this work. So let’s have that agreement in terms of figuring out what are essentially metrics of our success that I am committing to in exchange for this money. And so you will give me that money. I will spend it as I see fit to deliver that impact. And that’s my commitment to you. And if I don’t deliver on that, you can hold me accountable.” 

And so you change the conversation away from money for heads to money for results. And that’s, I think, essentially what Pavel was asking about. How do you frame it, not so that it’s about artifacts and outputs, but practice and impact.

And the mechanism I’ve seen that works best, it still takes quite a fair bit of management in order to realize its success, but is, OKRs, objectives and key results.

I had a boss, Jocelyn Mangan, she hired me at Snagajob, and she was a firm believer in OKRs. And OKRs done right focus an organization, not on output, but on impact. Key results should be about, How are we making an impact? Key results aren’t, “I shipped something, check.” Key results are “20% of people are engaged in a new activity” or, ”Revenues have gone up 35%,” or whatever, and you focus on those results and whatever it takes to get to those results, that’s up to the team to figure out.

That might be a mechanism that you can introduce to shift that orientation away from output and towards outcomes. And if you’re looking for resources on that front, Radical Focus by Christina Wodtke is probably the best handbook for OKRs that I am familiar with.

Jesse: It’s a good one. You highlight an interesting challenge in this, which is that in a lot of organizations, the way that design work is framed is not actually that much in the control of the design leader. That the way that the value is framed by the executive leadership of the organization is often filtered through the perception of design by your peers, particularly your peers in technology as, as you were talking about, design often ends up lashed to technology, as an enterprise level service in these organizations, then the models by which development and engineering are managed, then become the models that design inherits, because that’s what the executive leadership is used to consuming from their technology organization.

It then entails a reframing of what a performance metric even is in some of these organizations, to bring about the kind of conversation that you’re talking about to shift that perception. 

Peter: I like your use of the verb lashed, like somehow we’re kind of manacled or otherwise like literally bound to these technologies. So what you just said, I think connects, to Chris Jones, who sent us an email:

“I’m curious how you would consult a design team to better frame their unique value inside an organization that is crowded out by engineering voices and investment. How can I articulate the value the design team creates as being as critical as sound software engineering?” 

This is part of why, a number of episodes ago, we talked as much as we did about charter-building and team definition. Design teams don’t do enough to define themselves, which means in the absence of that, they are defined by the others around them and those that preceded them.

Unless a designer is a founder who is establishing a design practice, when the design practice is established, it’s established by a non-designer who has a set of expectations that are likely not as robust or sophisticated as we would hope. And so as design blooms within an organization, it needs to take that time to define itself in a fashion that’s distinct from the other parts of the organization. 

I just did this with a product design team. And there were two aspects that I think are interesting in this regard. One is, and I’m biased towards this term, as you’ll see in a moment, one is we define the design team as essentially bearing the torch for humanism within product development. That recognition that there are people at the other end, those people lead messy lives, and it is the design team’s responsibility to make sure that what we build connects with the humanity that we are serving, because frankly, no one else in product development is in this organization.

The product managers are primarily held responsible to revenue goals, and engineering is held responsible to software delivery. And so no one actually has that empathetic view of the customer. There’s an extractive view of the customer as a source, as a source of revenue, but not an empathetic view of the customer. And so let’s make explicit design exists to serve the customer in that way, because nobody else in this context is.  

And then the other thing you can do is, be very clear in your measures of success, the value that you see yourself bringing. I think there’s some concern that designers, you know, don’t want to be held accountable. It’s like, no, here’s a set of metrics. Hold us accountable. Please hold us accountable. But hold us accountable to stuff that we think that matters, that we can now get others to agree matters. We’re happy to sign up for them. Yeah. So you have to make the time and effort to be explicit about defining design within your context yourselves, and not let others define it for you, or allow it to have happened through neglect or ignorance.

Jesse: Yeah, you can’t just leave it out there and hope that it’s going to be all right. You have to take active control of the message about design and its value within the organization. And I think this comes back around to something that we’ve talked about in the past, which is honestly the need for a design leader, especially early on, to be something of a salesperson for design as a practice, more broadly, and not simply for the value that their team delivers, but the value of design itself.

Peter: Yeah. Looking at Chris’s question again, I think it ties into Pavel’s. “How can I articulate the value the design team creates as being as critical as sound software engineering?” And I think the way you do that is try to understand what does the company value. So in this instance that I was talking about before, the company valued revenue obviously, but, okay.

So if that’s the highest order bit that the company is oriented on, well, then connect what you’re doing to revenue. Show how the efforts of your team will generate more revenue. Maybe reduce the bottom line. It shouldn’t be that hard to connect the efforts of design to those levers that the business is most interested in, you just have to do the work.

When we did that ROI of design report a thousand years ago at Adaptive Path, we had this thing called the linking elephants. Where you connected a business problem with a desired behavior, you measure that behavior, you connect a value metric to that behavior, and then you identify a financial metric.

And so you can say, if, you know, we did this for a financial services client, if we can get 20% of our existing customers to open one additional account, so you have a checking account, we want you to open a savings account, or we want you to have a credit card with us. So the desired behavior opening an account. And then there’s modeling there that should allow you to spreadsheet that out.

But, it requires designers and design leaders to be willing to put on their business hat and work with spreadsheets, which is not something many are comfortable with. But if you want to make the kind of change that people are asking for in these questions, you now need to be part of that conversation.

Jesse: I think that’s true. I will say also though, that models like the linking elephants model presumed that there is a trail to follow there. That it presumes that there is something concrete that you can nail down and name at every stage of that investigation into the underlying value of the work.

But the truth is that that’s not always there. And sometimes the value that’s delivered really is not identifiable in as concrete away. And I think in cases like this, it becomes a question of culture, because the truth is that as much as we think of design as being unique in these organizations, in the sort of weirdness of design as a function, the truth is that most organizations have some functions for which the value and the impact are not tangible in this way. In these organizations, there will be a culture of decision making around how they measure the unmeasurable, how they qualify the unquantifiable, how they come to decisions about areas where there is value that they can perceive, but that value is intangible.

And if you can figure out where the other intangible sources of value are in the organization, learn about the culture of how the organization makes decisions around those things, you can then start to leverage those patterns in how you make the case for the intangible value of design.

Peter: My sense, based on the questions, is that these folks are in an environment where before they get to be culturally intangibly valuable, they need to be explicit and demonstrate some hard value first. I don’t think it’s an either/or, I think it’s a yes-and.

Jesse: I think these questions do come into play to different degrees based on the maturity of the design organization within the larger organization that they’re a part of because yes, in the early days, there is going to be a lot of proving tactical value. Getting those delivery wins in order to start to gain more attention. But then having to push it toward that broader strategic holistic intangible impact conversation because you can’t rely on your executives to do it for you.

Peter: That’s right. That is exactly right. My point was only that you can’t only pursue the cultural intangible.

Jesse: Oh yeah. Yeah. Just, sometimes there is no trail of evidence to follow.

Peter: Right. Yeah. If I think of engineering as really about building, maybe the challenge here is that there’s a building aspect of design, but then there’s the generative and creative aspects of design. 

I think the challenge that we see within the world of quote design unquote, is that there are two components of it that are kind of represented by both sides of the double diamond. There’s design work that can be used in a strategic fashion that identifies opportunities, that’s generative and creative and harder to measure. That’s where you’re going to be more in the intangible. And then there’s the design work in the second diamond. And that’s much more about delivery, much more about production, much more about tweaking to realize incremental gains.

Both are valuable, both are called design, but they’re really different parts of the value chain. They don’t think that that function that helps with delivery, you can take those same practices and generate that strategic understanding.

In either way, design gets dismissed. Design, if seen as a delivery function, design is not brought in to help with the strategic kinds of questions. But if it’s seen as primarily strategic, then design is sometimes just seen as a bunch of hand-wavy management consultants who don’t really know what it takes deliver value in the very end. And it’s just like, we can’t win either way.

Jesse: Right, yeah. I think that’s true. And I think that this leads to some of the confusion in the marketplace about what a UX role even entails. So we have these young people coming out of these UX programs and boot camps and so forth who think that they’re going to get to do soup to nuts UX out there in the world. And the roles that are available, you’re going to be kind of shunted to one side or another.

Music break  

Peter: So two questions that came in, both on Twitter, both addressed the challenges of being a design leader right now. Austin Govella asked about, “helping my team feel secure and supported when my own world is a drift on stormy seas,” and Joie Chung asked, “The main thing top of mind these days is maybe getting advice on how to help my designers feel safe and secure in rocky times, and especially keeping the morale up after dealing with layoffs of other teams and reorgs because of those layoffs. The key thing is there’s a lot of change and I can’t promise them there won’t be more.”

Jesse: Hmm. Stormy seas.

Peter: So we’ve got stormy seas, rocky times, its a lot of weather, and, nautical references.

Jesse: Well, there’s a lot of weather for sure.

Helping people hang in through layoffs and reorgs is tough. I think it puts everybody into a questioning mindset, and they start questioning things that are not actually up for grabs, but it can feel that way. It can feel like everything about a company is suddenly questionable when the leadership starts making these unexpected and rather dramatic moves. You know, this is where I come back to the stuff that I’ve been talking about all season, which is building emotionally resilient teams. And that has mostly to do with the people that you interact with every day and whether you feel like they are on your side and whether you feel like you are on theirs.

And if you were feeling strong alignment with the people around you, and if you feel like you can show up honestly and vulnerably with what’s challenging you, and can feel supported by the people around you, that goes a long way, because you can’t actually promise as a design leader that there won’t be more change. You can’t promise that that change won’t be really very difficult for people. You can’t insulate them. You can’t keep them safe.

Peter: You can’t promise that you’ll be there.

A glib answer to this that I still think has some merit is, it is up to the leader, even in difficult times, rocky and stormy times, to maintain positivity. If we extend the nautical metaphor, to point the way forward towards calmer seas, to orient people on not getting stuck in this muck, but problem solving around how are we going to get to a more desirable outcome and how do we focus our energies now. Not on worrying about what’s happening around us, that we don’t have control over,  but on doing what we can on the things that we do have control over, to make progress and to chart that progress and to recognize the steps that you’re taking to move things forward, and even if it’s very near term or very seemingly minor, getting folks focused on those steps towards something better.

Jesse: Yeah, I think that what you’re speaking to is a kind of a leveling up that the leader can do. To step back away from the immediate tactical churn of the moment and remind the team, if you’ve done charter work, as we’ve talked about on this show, then you have something to fall back on to talk about shared purpose. And if that charter seems to be in doubt in the current environment, then you have your own sense of purpose to fall back on. And this is something that I think is really critical for maintaining that positivity that you’re talking about, which I agree is absolutely essential, which is that you, as the leader, have to take care of yourself, you have to maintain your own resilience.

You have to maintain your own ability to bounce back in the face of these things. And what that means is making sure that you are, even in the uncertainty, even in the doubt, even in the face of all of it, remembering for yourself, why you do what you do and giving yourself whatever space, whatever time, whatever ritual you need to maintain that connection for yourself so that you can show up for your team.

Peter: Yeah, I… one) try to get plenty of sleep. I find that that has more impact on my personal mood than literally any other thing in my life. As you were talking, it reminded me of a leadership coach that I worked with through this former boss of mine through Jocelyn, she had an executive coach that she brought to work with all of her directs, including me. And this woman had a model that maybe you’re familiar with. I don’t know where she got it from, but it was this idea of the line. And there’s below the line and above the line, and below the line is that initial, emotional, visceral reaction that often is frightened, negative, worried, and her point is to acknowledge that which happens below the line, but don’t let that drive your behavior. Like sit with it, recognize it, work through it. But if you behave based on your below-the-line feelings, you are going to lash out.

You are going to yell, you are going to engage in negative behaviors that bring others down. And so what you need to do is figure out, how do you get yourself above the line, into a more, progressive, positive, optimistic, forward-looking space, that’s still true to the concerns that you were feeling below the line, but now your response is more measured and is one of taking charge, of taking positive action, of problem solving, of, again, that kind of forward motion.

So it’s not a simple reaction. Sometimes, it’s the simplest thing of, like, what we say to a five-year-old before they react: count to 10, take belly breaths. 

Jesse: Yeah. Yeah. Yeah. What you’re talking about is behaving intentionally and not reflexively. And those reflexes don’t always look like a big lashing out or yelling at your team or anything like that. Those reflexes can also look like procrastination. They can also look like suddenly becoming really, really vague in your communications or avoiding particular people or particular conversations.

There are lots of counterproductive reflexive habits that are driven by these emotional states that we find ourselves in, and yeah, there’s definitely a lot to leadership that involves simply being able to manage your own emotional states. And being able to process whatever comes up for you and to be able to hold yourself in non-judgment in the same ways that we’ve talked about holding others in non-judgment. In order to maintain, and this fear of trust and mutual support.

First, you’ve gotta be able to give that support to yourself.

Peter: Part of, I think, giving that support to yourself, whether it’s something you invest in directly, or your organization invests in for you, is recognition that you need your outlet, you can’t bottle this stuff up. You need a way to get this out. 

I mean, this was something that Maria touched on when we spoke with her, which is at some point you get to a point where simply talking to your manager isn’t enough. They’re not going to be the ones to help you. And maybe, depending on your relationship with your manager, maybe you can be frank about the challenges you’re facing. You can, you can expose a little bit of that negativity upwards, because you need their help. You need some guidance.  

Jesse: And a good leader should expect that, and be ready for it. 

Peter: Exactly, exactly. So that they can then help you work through that. Maybe even just talk it out. Sometimes it’s one of those things, it’s like therapy. Just getting it out of your head and into the world or sharing that challenge with someone else makes you realize like you’re not alone in it.

And that is enough to help you get from below the line to above the line. But then hopefully they have strategies for thinking about how to address whatever the specific situation is. If you don’t have that, that’s where you might need to find coaches, mentors, but it is incumbent upon you to identify people that you can turn to when things become difficult, or folks are just going to suffer with what you were just talking about, Jesse, in terms of kind of bringing it on themselves and kind of becomes this vicious cycle, even if it’s not aggressive, it might be, procrastinating or literally passive but it’s, it’s problematic. 

Jesse: Yes, there are a million paths to self sabotage.

Peter: How many have you taken?  

Jesse: I’m, I’m, I’m trying to catch them all just like Pokemon.

Uh, you and I, over the course of this first season of this show have often talked about the path of the leader as a fairly lonely one and a fairly isolating one and a fairly solitary one. And we often talk about what do you do when you’re the only one who can do the thing that needs to be done. And I think that what you point out is really essential for all leaders, which is not to stay alone. But to go find yourself a peer group and find some folks that you can turn to for support.  

Peter: Right. I want to, refocus on a word that both Joie and Austin had, which was the word “secure,” and Joie asks how to help designers feel safe/secure. Austin asks, “helping my team feel secure and supported.” And I think… I’m not certain… I’m thinking through this… I’m not certain that it is the design leader’s job to provide security, particularly in the face of this rockines, if that security feels like a false promise, right? 

You don’t want to mislead, and security might literally be misleading to your team.

Here, that security would be, “Everything is going to be fine. You’re not going anywhere. You’ve got a good job. Do work and it will all be okay.” That might not be true. And you might know that might not be true. And so don’t provide a false sense of security if that’s not going to help your team actually do what they need to, to address whatever the situation is. Austin used the word “supported.” That, you can do. That is within your control. You can support your team a hundred percent and you should do everything you can to support your team. Get them the resources they need. Give them the time that they need, give them guidance around how to move forward in the ways we were talking about. Maybe it’s baby steps on project work, and just focus on what we do control and try to ignore what we don’t control to make your way through, Right? 

So you can support them. But I don’t think you can help them feel secure. Their security is their responsibility. Through your supporting actions, through your nurturing actions, through your leadership and guidance, you are going to affect their security, but you cannot provide security. They are not your children. 

Jesse: You can definitely undermine a sense of security through your choices.

Peter: Well, right. And you will undermine that sense of security if you provide a false sense of security that then is not delivered on. As we discussed, then 

they’ll just lose trust, and then all bets are off. So, what I would say is focus less on security and focus more on trust. And engage in behaviors that encourage your team to trust you. ‘Cause that’s about all you’re going to have control over, and one another, because that’s all your going to have control over. 

Jesse: Yes.  Beautifully put. 

Peter: Does that distinction make sense to you? 

Jesse: Oh, yeah, that does make sense to me. Yeah, I actually don’t have anything to add to that. That was great. So with that, I think we ought to just say thank you to folks for sticking with us through these first 15 episodes.

Peter: Yeah, this is 15, huh?  Wow.

Before we go, I do want to shout out folks who sent us questions that we did not yet get to. This is going to be like Magic Mirror on Romper Room. I’m not going to give people’s full, I’m not going to give people’s full names. But Dan, Daniel, Shelby, Sharon: Jesse and I see you, we read you, we appreciate your questions. Some of those questions frankly are episodes in and of themselves. And we expect to get to them when we’re on the other side of this hiatus, we will not lose them, but we couldn’t get to it.

Jesse: All good questions, some of them we were so confident we would come back to, we wanted to give them enough space.

Peter: Exactly. Exactly.

So with that, we are wrapping up another episode of Finding Our Way, and wrapping up what Jesse and I have referred to as this first season, this 15 episode chunk. We are taking some time off for the summer. And so…

Jesse: Get out in the sunshine! 

Peter: That’s right. get some vitamin D, limit our exposure to COVID and episodes should be be coming out again, sometime, we think in the late-ish August timeframe. 

Jesse: Right around Labor Day, plus or minus. 

Peter: Yeah. And so until then, we thank you for joining us on our journey, as we have been figuring out how we find our way through some of these challenges of design and design leadership.

And just because we are not publishing doesn’t mean we’re not around, feel free to hit us up on Twitter. I’m @peterme, he’s @jjg.  You can find us through our website, http://findingourway.design/, where you can also find all of our episodes, transcripts of every episode, and then a contact form that we read.

That’s where some of the questions that we have received came through. And until then have a great summer, take care of yourselves. Take care of those around you. And we look forward to further discussions in the future. Thank you, Jesse.

Jesse: Finding our way. 

Peter: [Singing] How many roads must a man walk down before he is a… 

Jesse: Is the, this is the musical episode, finding our way.

Peter: [Singing] A whole new world.

Jesse: Peter, what are you doing?

Peter: I’m singing. I had a, I had a double espresso, on top of my morning coffee, so I am good to go.

Jesse: Oh man. Well, I should have been more prepared, I guess…

Peter: You can…

Jesse: I thought we were going to sort of take it easy here for the last…

Peter: You can be yin to my yang.

Jesse: Isn’t this where we came in?

In which Peter shares some of his Design Leadership Truisms (inspired by the work of Jenny Holzer), and Jesse reacts.

The image that spurred the episode:

Truisms discussed:
“People are not their job titles.”
“If your team’s work isn’t good, you didn’t set clear expectations.”
“Bad design is a result of context, not individual aptitude.”
“If you focus on the organization, quality will take care of itself.”
“You cannot calculate an ROI for design.”
“If you haven’t pissed someone off, you are not doing your job right.”
“For someone who talks a lot about empathy. You show little for your colleagues.” 
“Introversion inhibits design’s ultimate impact.”

Peter: Welcome to Finding Our Way, the podcast where Peter and Jesse welcome you to their journey as they navigate the opportunities and challenges of design and design leadership. I’m Peter Merholz and with me is Jesse James Garrett.

Jesse: Hello, Peter.

Peter: Hi Jesse.

Jesse: So we were riffing on in email other things that we could talk about today and sort of almost in passing, you shared this image with me, which, is this a slide from one of your talks?

Peter: Yeah. So, last October I spoke at the Design Leadership Summit and I gave my design leadership talk called “Coach, Diplomat, Champion, Architect:  The Four Archetypes of the Design Leader.” And when I first gave this talk, at the very end, I tacked on what I called “hard truths about design leadership,” and it was a series of statements.

And I realized before this event, because this event was a little more homegrown, a little less polished, I felt I could play with it a bit more. I actually ended up pulling up those statements at the very beginning. And what I did was essentially a cold open, so I walk out on stage, you can see in this… there’s a YouTube video, I walk out on stage wearing all black. A black shirt, black pants. And the title slide says “Design Leadership Truisms, from mer-Holzer” because I’m trying, I’m playing on Jenny Holzer, and her work with truisms. And then I just state each of these truisms.

And then the slide I gave you was all those truisms on one slide, just like, here’s everything that I just shared. And I ended up doing that as this preamble to my normal talk.

Jesse: I love this. So, first of all, I definitely, when I was reading the slide, detected the Holzer-ian nature of it. Her work is something that I’ve admired for many, many years. And I think anybody who has read any amount of what I’ve done can detect a trend toward the aphoristic.

Peter: Declarative aphoristic.

Jesse: Yeah. Yeah. The desire to reduce ideas down to their most potent and concise expression. And that is something that I’ve always admired about Jenny Holzer’s work as an artist as well. And so you sent me this thing, and that sounds awesome by the way, dressing all in black. I think it’s always a smart look. 

And I just started reading a couple of them and I was like, I have opinions about these. And then I put it away. And I was like, I want to talk about these opinions later. So there were a couple of these that I’ve glanced at for a while…

Peter: So is now later? 

Jesse: Later has arrived, Yes. And I thought it would be fun for us to just read through them and talk about them and see how many we get through in the time that we have. And, maybe see if there are any of them where we have any particularly interesting reflections or points of contention. 

Peter: Why don’t I read them?  Since I wrote them. 

Jesse: Okay. In fact, what I’m going to do is I’m going to put the slide away, so I’m not looking at it. So I’m just listening to you read.

Peter: Great.

Jesse: Implicit in this, I sense, is the idea that you should not treat people like they are their job titles.

Peter: Yes, basically, too often we are encouraged, particularly as managers, to reduce people to their job title and then swap people with the same job title and treat them the same, treat them interchangeably.

And we need to engage with everybody as individuals. A job title should not define anyone.

Jesse: Well, I think, especially when you’re talking about design roles, where the particular background, the particular creative strengths of the individual are going to very, very strongly influence the results that you get, I think that is definitely true. 

I think there is a spectrum. That there are some roles that are more operational, that are processes that can be taught. But in the case where you are looking at people who are going to make a creative contribution to where the entire endeavor is going, in those cases, you do want to look more closely at the individuals and what they bring to the table.  So yeah. Yes. And yes.

Peter: I’m not going to read them all. I’m realizing I’m going to skip a couple. 

Jesse: You should definitely choose because there are too many. 

Peter:

Jesse: I’m going to say no to this one. I think that there are lots of ways in which a team’s work can go wrong. I also think expectation setting from leaders can go awry when the leaders themselves are not clear on what they want. So there’s knowing what you want and then there’s communicating it. And those are separate skills.

Peter: Right. So that would be not setting clear expectations.

Jesse: Okay. Fair.

Peter: Behind this, is talking to design leaders who are frustrated by the quality of the work their team is producing, but then when you ask them what they have done to help people understand what is acceptable in terms of quality, you realize the answer is, “Nothing.”

I’ve literally had conversations with design leaders who basically imply that they feel other people should read their minds as to what is an acceptable level of quality and deliver on that.

Jesse: I hear that. And I definitely have seen that. And. I know that I have gotten impatient in the past with designers when I felt that I had to explain something to them that I felt they should already know about what constitutes quality in design, and that impatience for me came from an expectation that I wouldn’t have to be teaching as much as I found myself teaching in that role, in that context, in that moment, especially in the context of consulting work, where there was potentially not really enough time to teach skills along the way as we were trying to meet client deadlines. 

So I think there’s an element in this of how much mentorship is the leader willing to take on, in bringing people along with understanding their expectations. And what do you do when that gap really does exist, when there is somebody who simply doesn’t understand the baseline thing that you thought you wouldn’t have to explain.

Peter: There is no universal standard for quality when it comes to design.  

So when I talk to these design leaders and I ask them, so how does someone deep within your team know what good looks like? And when they think about it, they respond, “Well, I guess that’s their manager helping them, like through direction or critique or review.” 

So design quality, two things there. One, it becomes very localized, and so different managers with a different understanding of quality might be managing towards different quality within the same organization. And two, it’s largely folklore, it’s spoken. It is not codified, and that raises its own challenges. Because something that’s not codified can become quite arbitrary. It can change, and that’s not great. 

One assumes that, if you are hiring someone, they know what they’re doing, right? You’ve gone through some process to vet their ability. And if they’re not doing good work too often, I find the design leader thinks that they don’t know good design. When in fact they don’t know what good design looks like in this environment or what is expected of them.

Jesse: So definitely I hear in that, the trap of assuming that your standard is a universally held standard, that is therefore universally understood by your fellow professionals. Right?

Peter: Right. I have a few elements here on this that are related to quality. Let me read the next one. 

Jesse: So what you’re saying is a good designer can produce bad design if they are in the wrong context. And it seems to be letting the designer off the hook a little bit in terms of what they bring to the table. This seems to imply that individual performance issues are more often a sign of organizational dysfunction. Either that dysfunction exists at the level of recruiting and hiring, or it exists at the level of performance management and mentorship and skills development.

Peter:

Jesse: Hmm. I don’t think I believe that. In fact, I think that articulates a gap that I am trying to fill in my work, in that I think the quality arises out of high-trust, collaborative relationships and not out of organizational structures.

Peter: I don’t disagree. I think I would place that as an organizational matter, the point of this being, design quality is often not addressed until you’re looking at output. When, in fact, what drives that output was heavily determined by a series of factors long preceding that output, that I am maybe broadly labeling is organizational, but I would also argue organizational as opposed to say procedural, or a matter of process.

Jesse: Okay. So what is the distinction between organization and process in your view? Because I guess that those things are very much intertwined to me.

 Peter: So I wrote a whole book on organization and never really addressed process, except for including the Double Diamond briefly. When we talk about design, we often talk about process—that’s a thing you can talk about ‘cause it’s set of activities, it’s a set of methods, it’s a shared understanding that we can bring to the conversation.

What we often don’t talk about are the organizational factors behind the scenes that lay a foundation for the activities: how you recruit and hire, how you manage, how you mentor, how you grow, how you value, how you coordinate in relationship with one another within design, and how you coordinate In relationship between design and other functions. All of those things are the organizational matters.

Your internal agency organization can be practicing user centered design.

It’s just going to find itself highly constrained because all that user research is almost for naught because it’s not actually able to drive the upfront thinking because, organizationally, the designers aren’t in the right relationship with their peers, with the power to make that change.

Jesse: I guess there were a few different ways to think about it. So, there is a football analogy that comes to mind, which is that you have the players on the field and the players are playing certain positions. And you have different ways you can line those players up according to those positions. And there are different positions you can deploy on the field, according to your needs. And so that feels like the organizational stuff. Who are the players on the field? What are the skills that I’m putting out there to accomplish my goal? 

And then you’ve got process, which is the playbook. Once you get the players on the field, how do they interact with each other? How do they move in an organized way toward a goal? 

And then you’ve got the people stuff at the individual level of the stuff that you’ve been talking about, recruiting and hiring and making sure that the guy that you have brought in as wide receiver is actually somebody who is suitable to be a wide receiver. 

But I think there’s this other level, too, of team cohesion. And this is something that I’ve heard you talk about, about how the coordination, the orchestration of the individuals who are performing these roles in the context of this process and ensuring that they stay in sync with one another along the way. And that’s the rocky shoal that I’ve seen too many corporate ships run aground on. They got all the organizational stuff right. They got all the process stuff right. But no one was looking after the people. No one was looking after the relationships and it all fell apart along the way.

Peter: Hmm, I guess I would say if you’re not looking after people and relationships, you’re not looking after the organizational stuff. You might be architecting an organization.  

Jesse: I guess that’s the thing that I hear in this that I would push back against, is the architectural impulse to think that you can solve all of these problems, a priori, before any people show up in the door.

Peter: Yes, that I believe. Part of my point is to shift the focus, though, away from process and even, again, individual aptitude, towards matters of organization. And I would include relationship within that, because as I see it, when you have an organization, you don’t only have the structure, but you have the connection between those elements and, yes, you could even look at that architecturally, but there’s a relationship there that I think matters and is part of what I intend when I talk about organization.

Jesse: Okay. Well, thank you. That’s clarifying to me.I don’t know if I have a particularly narrow view of it, or if I have inherited a particularly narrow view of it from the things that I’ve read, but I tend to think of the organizational stuff, in terms of let’s figure out management reporting, performance management, incentive structures, that will ensure a certain quality of outcome.

And I don’t think that stuff goes far enough. And I agree with you. I don’t think the process stuff goes far enough either.

Peter: Well, and my sense is folks focus on that which they can get their hands around, and the structural organizational stuff is easier. But insufficient. It’s the same reason that one of the challenges that we have in delivering good designed experiences is we end up getting nudged towards delivering only on that which can be measured. Through monthly active users. And, how far down a funnel someone gets, et cetera, et cetera.

And we lose sight of this stuff, which can’t be measured, but which is as important in terms of the nature and the quality of the experience. And that comes from a bunch of ineffable details that someone is having engaging with an experience. And the same thing happens with organizations where they over-focus on that which can be measured and modeled, and lose sight of the messy stuff that, as you’re pointing out, is kind of the beating heart of those organizations.

Jesse: I think a corollary of this is the tendency of leaders, when they find themselves challenged by their circumstances, to fall back on those areas where they feel the most empowered, and often the areas where they feel the most empowered are the areas where they feel they have the most control, where they feel like they can dictate circumstances rather than be subjected to them. And so this is where you have leaders run into challenging times and declare it’s time for a reorg, and the team is like, great, this is another challenge on top of the challenges that we were already facing, because reorgs create just immense waves of chaos and confusion through organizations.

But from the leadership perspective, it can feel like they’re taking control of the situation, when in fact all they’re doing is retreating to the things that they do feel some level of control over, because they don’t know what to do about the things that they don’t.

Music break

Peter:   

Jesse: Ooh, I suspect that’s almost certainly true, but I’d love to hear your articulation of an argument for it.

Peter: So in 2002, Adaptive Path attempted to unpack the notion of an ROI for design, an ROI for user experience. 

What we found was that you couldn’t calculate an ROI for design because design is too integrated with too many other activities, that you can’t isolate design in any meaningful way. That said, what we saw was when you consider design as a lever for business value, when it was involved in the right conversations, when those activities of design were informing strategy, then those businesses both seemed to fare better, and the design teams were much happier, were much more engaged and did what was believed to be better work. 

Jesse: I think a lot of this has to do with how UX design has always grown up in the shadow of engineering and engineering management practices and the strong cultural trend within engineering management to attempt to quantize and reduce the work to something that is measurable factory-like piecework.

I mean, one of the most legendary pieces of writing in software engineering management is a book called The Mythical Man Month, which is about, in fact, how you can’t effectively quantize a lot of these things, because you can’t reduce software engineering to that kind of piecework. Software engineering management methods have adapted a lot in the time since that book was written, but there is still this desire that I see in waterfall and agile and everything that’s come since to try to squeeze the work down. 

And design is even weirder. A very small amount of design can deliver a vastly disproportionate amount of value across an entire product in a way that the same chunk of development time can’t accomplish the same thing.

And I think that is the disjunct between engineering management practices and design management practices that leads to these breakdowns that we see in these organizations.

Peter: Totally. That’s exactly—…

Peter:  

Jesse: I think that’s true for as long as design leaders continue to be forced into the role of cultural change agents within organizations, for as long as we are continuing to have to fight for the voice of user research in strategic decisions. As long as we are having to continue to argue for experimentation and collaboration and iteration and adaptation in business strategy and design strategy and technology strategy, we are going to continue to be in this position of resident gadfly within organizations.

My hope is that eventually we get to a place where we have more leaders who understand where we’re coming from, and we don’t have to piss as many people off in order to make our points. It’s an outstanding question for me, whether that is actually possible.

Peter: Right. And there’s a kind of double-edge to this because, you’re talking mostly around a design leader, working with non-designers, and pissing them off as part of change. There’s also, if you haven’t pissed someone off within your team, you’re probably not doing something right.

Jesse: Okay. This, I would like to hear more about. 

Peter: Well, right? Because leadership requires making hard decisions and you’re taking a lot of different stuff from different people. But as the leader, you are the one with the authority to make a decision and set a direction.

And that will likely go against somebody’s input that was delivered to you. 

I’ve hired people over the objection of folks who were part of the process, because I felt that their contribution, while informative, was essentially misguided, and I had to make a hard call of who to hire between two candidates.

And I made a call that ended up pissing some people off. 

I could have either tried to make a more popular call, hiring the person who people were more aligned with, but I didn’t feel that was the right call.

I could have tried to ameliorate, maybe, say, “Let’s not hire anyone.” Let me make a decision by not making a decision. that probably wouldn’t piss anybody off. They might not be happy about it, but they wouldn’t be angry about it. But instead, I made a decision that actively upset someone.

I think too often design leaders, in trying to get along, in trying to make everybody happy within their team, either defers decisions, or doesn’t commit to hard decisions because they’re afraid that they’re going to make somebody on their team unhappy.

Jesse: Yes, I think that’s a risk, but I think this goes against some of the things that you’ve been saying in terms of recruiting and hiring and bringing people into the team that you feel are strongly aligned with you as a leader, people who are strongly aligned with your values.

If you, as a leader, are regularly making decisions that are pissing off your team, you don’t have the right people on your team. There’s some breakdown in alignment there between your intentions, your values, your perception of the problem, your perception of what’s needed for the solution, and the perspective of your team.

And if you aren’t bridging that gap, you probably are working with the wrong people.

Peter: That’s fair. I see what you’re saying. If in a group of eight, four or five folks are upset, then yes, you clearly have a misalignment. And if in that group of eight, one or two folks continue to be upset over many months, that’s, I think, the kind of misalignment that you’re talking about is likely happening. 

If in that group of eight, over the course of a year, you try to never make anyone mad, so that what you value is not making anyone mad over making the right decision, that’s where the problem is.

Jesse: Yeah. So I might flip this statement around and say, “If you’re never pissing anyone off, you’re probably doing something wrong.”

Peter: Okay. That’s fair.  

Jesse: Ooh. Yeah, I definitely feel this one. I’ve definitely seen this one a lot. 

Peter: Have you done this one?

Jesse: Oh, yes, I, yes, definitely. I, I have definitely fallen into the trap of the us versus them. The sense that we, as the designers, have some unique Batphone to heaven that communicates to us the absolute truth of things, and everybody else is misguided and in need of education and possibly angling against us. 

And, yeah, I think that’s definitely a real risk, especially if you’re, if you are a design leader who has to fight against the cultural tides all the time to demonstrate that you belong at the table to prove the worth and the value of the work that your team is doing. If you are contending with that stuff all the time, this is a very easy mindset to fall into.

Peter: Yeah, one of the things I say, both when I give this talk formally, and then it’s been coming up over and over again with this team definition work I’ve been doing with some design teams, is the phrase “assume good intentions.” And I think when we say it, we’re like, Oh yeah, of course. We’re all trying to do the right thing. And we’re engaging from wherever we’re coming from. 

It’s easy to say, it’s harder to remember.

Jesse: I think that’s a really important overarching point. In general, that generosity of spirit that I think is necessary to maintain the optimism that this work requires of design leaders. If you are going in every day with the attitude that the whole world is against you, it’s going to be hard for you to muster and maintain the positive energy required to motivate a team toward creating something new and valuable in the world. And I think that that is a lesson that really underlies so many of our relationships as leaders, whether they are relationships with the leaders above us in organizations, whether they are the relationships with our peers, whether they are the relationships with our teams to try to assume good intentions as much as possible, I think is essential. 

Peter:

Jesse: Oh man. We could do a whole episode about introversion because I think that introversion has become a fucked-up trap psychologically for creative people. And I think that people’s commitment to their identities as introverts is undermining their success broadly in the world. So, yes, I totally agree with this one.

Peter: Wow. And here, I thought, as my favorite, highly introverted colleague,  that you…

Jesse: Oh, yeah, but I’m a self-hating introvert. I think my own introversion is absolutely maladaptive and I actually have a lot of judgment toward other introverts. I think that introversion as a cultural identity provides a very safe way for introverts to run away from their own insecurities and interacting with other people. And it does them a disservice to allow them that escape.

That’s pretty harsh. I know. 

Peter: No, no, because, well, this is the one of the 25 that I actually heard back from more, probably than any other one, like, in the hallway or, you know, maybe on a Slack message.   

Because, well, one) design as a profession tends towards introversion. Understandably, right? In order to be able to sit, often by yourself, for long periods of time producing work, that takes an introvert’s mindset and capacity. As you grow as a designer, at some point, introversion becomes a challenge. If you’re not able to speak up, if you’re not willing to put yourself out there, if you have trouble communicating your rationale, as you become a leader that introversion becomes this deficit.

Because in order to lead, as we’ve said, you need to relate. You need to communicate, you need to put yourself out there. Introverts have a harder time of that. And what ends up happening, the reason for this phrase is, functions that are more extroverted–marketing functions, product manager functions–when you’re in those contexts where cross functions are getting together, it might be to do the work, but it might also be kind of an all hands and an evangelism moment, extroverts tend to dominate those spaces 

Jesse: Yes.

Peter: Product managers then grab the mic at the all hands and talk about the great work that their team has done. And the designers don’t see their design leader doing something similar. They don’t feel that the product manager represents them, even if their work supported the work that product manager was doing.

But the design managers, if they’re an introvert, is, like, “Well, the product manager is speaking for the whole team,” or, “I just don’t, I don’t like, it feels fake to get up there and go rah rah, I’m a designer. I’m going to play it cool.” All that kind of stuff. 

We probably should take an episode to dig into this because I want to be respectful of introverts. I work with them, I live with them. And as part of a desire to be big-tent, to accommodate all neurotypes of backgrounds and experiences, it’s not fair, for lack of a better word. It’s not fair that introverts are put in an uncomfortable position that in order for them to continue to succeed, they have to overcome this aspect of their personality now. But it’s also, at least in the current moment, real. Extroverts thrive in this professional environment in a way that introverts do not.

And I’m mostly just trying to call attention to it. My hope was that in 5 to 10 years, we can figure out contexts in which introverts and extroverts can be their full selves as introverts and extroverts. And neither is advantaged. 

What you said suggests that you might not feel that way, and that introverts need to get over themselves and their introversion. 

Jesse: My perception, and this may be ungenerous, and it may be that my own status as an introvert qualifies me to make this assessment and maybe it doesn’t, but my perception is that most introversion comes down to a frankly, very childish, “I don’t wanna. I don’t want to have to explain my work to other people.

I don’t want to have to figure out from moment to moment what somebody else is thinking of what I have to say. I don’t want to engage,” and that’s not productive and that’s not how humans get anywhere together as a species and this privileging of your own comfort over the success of your work is never going to serve you as a creative professional. So that’s my point of view.

Peter: Kind of like we did when we wrapped up that one episode, talking about trust and realized that we had a lot more to get to. I have a feeling, I have a feeling that is true with this topic as well. 

Well, we didn’t get through all the design leadership truisms. We probably got to about maybe a third, probably a quarter of them. So this can be…

Jesse: We can do another round, maybe next season.

Peter: Yeah, yeah, exactly. But that wraps up another episode of Finding Our Way. As always you can find us out on the internet in various forms. On Twitter, I am @peterme. Jesse is @jjg. You can also find us on our website, http://findingourway.design/, where we have all the episodes posted, including with full transcripts, and there is a contact form that Jesse and I read everything that comes through. And that is how many people have reached out to us so far,  which has been great. We’ve had some interesting feedback, from folks through those means. So, yes, please reach out, let us know what you think. Give us ideas for future conversations.

And until then, we hope that you are doing well on your journey as you continue finding your way.

Jesse: Finding your way. Thanks Peter. 

In which Jesse and Peter discuss their relationship to systemic racism, as individuals, as leaders, and as members of the design and UX communities.

Peter:  Welcome to Finding Our Way, the podcast where Peter and Jessee welcome you to their journey as they navigate the opportunities and challenges of design and design leadership. I’m Peter Merholz, and with me is Jesse James Garrett. 

Jesse: Hello, Peter.

Peter: Hello, Jesse. What are we going to talk about?

Jesse: Well, yeah. I mean, I think there’s an elephant in this room that is getting larger by the day. And, I think it would be useful… What we hear, what I have heard, what I have read from people of color about the conversations that need to happen about race in this country. One of the big things that I have heard is, “Don’t come talk to me about your racism. Go talk to each other about your racism.” So I think it would be great for us to talk to each other about race and how race has played out in our careers and how we see race playing out, all around us. But especially, you know, you and I are in a position where we have, quite a history of choices to interrogate as designers and as collaborators and as design leaders. And I think that all of those are topics worthy of exploration.

Peter: I agree. The subject has come up with some of the people I work with, where, particularly, the white men don’t quite know how to navigate this conversation with their teams. They’re like us—they’re middle aged white dudes whose hearts are in the right place, but, almost don’t know where to begin.

Which is frankly kind of where I am, okay, when it comes to this.

I gave a presentation yesterday to UX Waterloo, a local IXDA chapter in Waterloo, Ontario, which is about an hour outside of Toronto. And during the Q and A, it came up, you know, basically asking, “What should we be doing during these strange times?”

And, I don’t have a good answer beyond, “Listen” at this point, still, though. It’s probably time to start turning that corner from listening to acting. I’ve been thinking about how I could act, but then I allow myself to get distracted ‘cause it’s hard. And, there’s, you know, any number of things competing for my attention.

And I choose to deal with the things that I feel like I have a handle on. 

Earlier this week, I took part in San Francisco Design Week. Every one of their sessions has a link to the Inneract Project. I N N E R A C T, which is a cause to support bringing more Black and Brown folks into the design field, going into schooling and then supporting them all the way into joining the profession. So getting involved with Inneract, I actually signed up to conduct pseudo job interviews for early stage Black and Brown designers.

Jesse: Like practice interviews for them to sharpen their skills. That’s awesome. 

Peter: A link had come across, in one of the community Slacks I’m part of, and it was really easy to sign up and say, “Hey, I’ll do this.” And here’s the time.

Those are small ways, but it’s not something I’ve really sat down to work through. I know that you are going through these coaching classes and are developing a toolkit or an approach to tackle and work through some more challenging stuff. And I’m wondering whether from that or stuff you’ve learned prior to that how you are thinking about this, what tools you have for yourself and perhaps for others you’re working with to ddress these challenges.

Jesse: Yeah. This stuff intersects, in that the work that I’m doing is about how leaders show up day to day and how they navigate these more flexible, more fluid, more challenging kinds of situations. And this stuff actually started coming into play for me in my role at Capital One. 

Peter: You say “this stuff,” specifically, matters of diversity and inclusion, racism. Yeah.

Jesse: Well, yeah. I mean, diversity and inclusion, I think, is the nice corporate frame that we put on what we’re actually talking about, which is systemic racism.

Peter: Yeah, yeah. D & I became this initiative that we have a director of it. So we’re doing what we can…

Jesse: Yeah. I mean, it’s an easy way for an organization to flag, you know, this is important to us. We’ve heard you. And so we have appointed a person, and I ended up as that person for the team that I was supporting. I was coaching the leaders of a group of teams that were all under one umbrella that was collectively about 80 people.

And as coach to the leadership team, I was charged with thinking about, as we’ve talked about, these holistic systemic issues going on across the team that were impediments to the team success. And this bubbled up, it really was something that the staff took the leadership to task basically, and said, “We don’t feel like you guys are taking this seriously enough. We don’t feel like the answers that we’re getting are satisfactory, and we don’t feel like we’re seeing cultural change in the ways that we want to see,” in terms of, especially, whose voices got heard, how recognition happened, and then ultimately, obviously, how, power and authority get distributed in an environment like that.

And the leadership turned to me and went, “Well, you’re our holistic systemic problem solver. Here’s one.”

Peter: ”Can you, can you solve racism for us? Can you model it?”

Jesse: Well, it wasn’t exactly that. It was like, we know that this is not how we want to show up as an organization, and, we want to be the vanguards of this change. We don’t want to wait around for somebody else to tell us how to create it or tell us at a corporate level what the official approach was going to be. We felt we needed to generate something of our own. And so we jumped in with both feet, and set out to create some safe spaces for these conversations to happen.

And I would say we got very, very mixed results with that.

In fact, I would say that the people of color on our team probably would say that “mixed results” is a generous assessment of how that went.

Peter: What were the obstacles for, what were the barriers?

Jesse: I think the major mistake that I made was not fully understanding what, creating these formalized structures, what position that put the people of color on the team in, in terms of having the spotlight put on them and their experiences in a way that they may or may not be ready or willing or eager to share, or the feeling that they are going to be put in the position of having to explain systemic racism to a room full of white people and that they are going to have all of this extra stuff put on them, this extra emotional burden of having to talk through their past traumas,

Peter: Right. “It’s not bad enough that we’re subject to the systemic racism our entire lives. We now have to educate you about it.”

Jesse: Right. And in an effort to create a sense that the leadership was actively engaged in this process, and actively engaged in listening, we had our leaders facilitate these conversations and our leaders did not have the skillset to facilitate these conversations, first of all. And secondly, we did not, I did not, really fully appreciate how the power dynamic in that room, when you have the leader facilitating the conversation, was going to skew things. And so, there were a couple of really fundamental misunderstandings that I had of what I was doing that led to that whole approach not working for us.

Peter: Yeah, there are times when leaders should be playing the role of facilitator in an effort to quiet their voice and elevate others. And sometimes it’s the right solution. But I think when it’s charged, if there’s an emotional tenor to it, even if they try to be as dispassionate or blank as possible, just the fact that they are the leader colors this, and you need, probably, ideally someone who has almost no context, no agenda that they could be accused of falling back on.

Jesse: Well, and I think part of the reason that I was tapped for that role was that I was not a leader of a team. So I was not in that same position, but I wasn’t facilitating sessions.

But yeah, honestly, and this was the reason I had to get out of Capital One altogether, I was, at the end of the day, embedded in the power structure. And could not play that outsider role to the extent that I needed to in order to be successful as a coach.

Peter: Right.

Jesse: So what we did after that, then, was we went and got some help, and we hired a consulting group out of Oakland called Circle Up. And they do consulting and workshops around helping organizations have these kinds of difficult conversations. And they led us through a process that was very helpful and enlightening to us.

And we were just starting the process of engaging with them to actually train up leaders, to have better facilitation skills around this stuff, at the time that I left the organization and handed that work off to others.

Peter: Right. How do you get people to expose themselves? Candidly, honestly, frankly, in an environment like that, where even if it is a safe space, there’s a fair degree of risk. Whether you feel risk based on your employment status or just risk in terms of exposing your own ignorance. I have to imagine that no one is being open and honest in these conversations. Were you able to get there?

Jesse: It’s challenging. It is tremendously challenging. It comes back to the stuff that we’ve been talking about actually, which is that when you have a high trust, high interpersonal connection environment, these kinds of conversations are easier. When you have people who are habitually, practicing things that we’ve talked about. Non-judgment. People who have practices of curiosity in their work. If these are your cultural values, then it’s going to be easier to get there, but still it is touchy stuff. But it’s too important not to do. And so I think that as leaders, we have to be willing to acknowledge what we don’t know and acknowledge that this is a problem that is not going to be solved in our lifetimes. And so we can’t ever craft what we as designers always want, which is that perfectly honed, eternally right solution. It is all satisficing what we’re doing right now. It is cobbling together little bits of things and making mistakes and learning from them. I do think that relationship as a frame is really important for this because when you talk about leaders as facilitators, what I’m thinking about are all of the relationships that that leader has with each individual in the room and how all of those dynamics get piled up on top of each other.

And the effectiveness of that group environment in a lot of ways depends on How is the leader doing in their relationships with their people individually? And are there things that are unsaid in those relationships that have been bottled up waiting to come out? If that stuff is all there and then you ask that of people in a group environment it’s going to be really hard.

So one question that I would put to leaders is how are you one-on-one’s going?

Peter: So a project I’m about to start, there’s a leader who is extremely eager to get going and solve a problem and dive into the mechanics of solving the problem. And based on my initial assessment of the situation, I feel like the people who would be engaging in solving this problem, many of whom are direct reports of this leader, will not bring their full selves, if it starts with problem solving, and I’m like, “I need to have one-on-ones with all these individuals and try to get at some of the underlying stuff. ‘Cause I think there’s basically relationship stuff, relationship baggage, et cetera, that is affecting people’s abilities to act in their fullest. And if we don’t acknowledge the relationship stuff, yeah, we can kind of muddle along and talk about some solutions and probably, make things better, but the ultimate effectiveness will be blunted. And there are times, and this is one, where it’s not about great design. It’s about how we are engaging with one another. We have to resolve that and then we can get to the great design. But if we just start with, let’s just make design great, without acknowledging the underlying relationship stuff, you will never actually get to great design.

Jesse: That’s right. That’s the premise of my whole everything I’m doing right now.

Music break

Peter: Something you said though, you’re talking about power dynamics. One of the things that has occurred to me, as we’ve had these conversations about leadership, and which has forced me to just think more intentionally and reflectively about leadership at all times, is that I don’t think many leaders recognize the responsibility that they take on as leaders. That their actions have all these knock-on follow-on consequences. They don’t receive it as a responsibility beyond, “Let’s make something great. Let’s get to the next place, I am leading us towards something.” 

Jesse: It’s almost as, as if all of their sense of responsibility is directed upward in the organization, their responsibility to their leaders, rather than their responsibility downward toward their teams.

Peter: Right, right. Yes. You know, there’s the line from Spider-man, “With great power comes great responsibility.” And I think a lot of leaders don’t recognize that the power they wield has these impacts on people throughout their organizations, intentional or otherwise, that they should be responsible for, but it’s not often seen as a responsibility.

I think people assume to be a leader is to do good things, is to take us to good places, and through all of my actions, that is what will happen. And like, on all this stuff I ever hear about, or read about, or am thinking about, when it comes to leadership, there’s this lack of a recognition that your actions will affect people, and might affect people negatively.

And that just doesn’t resonate. And I don’t know why we hold our leaders accountable, but we don’t hold them responsible, and…

Jesse: They’re accountable when things go sideways, right? When a team blows up, because this stuff came into play in a bad way, then it’s like, “Oh, leader, you should’ve known.” But until that happens, the organization is happy to pretend that none of this stuff ever exists. And I think that you’ve hit on something really important, which is that leaders are not just there to perform and deliver. Leaders are cultural stewards for their organizations and have to cultivate cultures that do not harm the people who are in those organizations.

Peter: That’s right. I think that’s exactly right. You know, in prior episodes we talked about the distinction between management and leadership. And I think with management, there’s this recognition, because you have direct reports and, part of your job is to grow your team, that management has a responsibility, in this way.

But somehow we don’t use the same language or the same frame when we talk about leadership. But I think, to your point, successful leaders, because they are these cultural stewards, because they become models within the organization, often have a greater impact on these factors than the managers do.

But again, they don’t see that as part of their responsibility. And something that I’m starting to come to terms with. 

Another theme that’s emerging for me is that I want to discourage most people from embracing leadership, because not only is it hard, it has these outsized impacts that I think most people assuming leadership are not ready for. And are not aware of and are not cognizant of, and, because of that, it’s the baby with the gun. They’re wielding this influence and not doing so, appropriately.

Jesse: Right. But, with these issues, I feel that an overabundance of caution represents a different kind of harm.

Peter: Well, it’s a challenge that I feel personally. I am over-abundantly cautious when it comes to speaking about racism, systemic racism, my privilege. I will defer to, “Let’s listen to the Black and Brown folks.” ‘Cause what could I have to contribute as a middle aged white guy? And partly that’s true. I haven’t had those experiences. Idon’t want to take the stage away from others who are better suited to address it. But part of it is I’m afraid of saying the wrong thing. I am abundantly cautious because I have had a career of speaking my mind, and getting into trouble often for it.

But the trouble is around whether or not everyone is a designer or the trouble is around information architecture versus visual design, and subjects that were not truly charged in the same way that this is. And, a fear I have is that, with all good intentions, I will put my foot in it and get called out and I’ll get canceled or whatever, right? Because I’ll say the wrong thing. And that is what I’m seeing happening with some of the people I’m working with. Middle-aged white dudes running these sizable teams who are paralyzed when they’re at their all-hands.

They’re just like, “Can I just have the person of color, who’s maybe one of my directors, talk now because that’s the right thing to do, right, is to make a space for them? Problem solved.” 

‘Cause they don’t know how to act or what to say, because they’re afraid if they say the wrong thing, now they’re going to get canceled in some way in their organization.

Jesse: Congratulations. Welcome to leadership. Leadership entails stepping into unknown situations with uncertain outcomes and choosing a course and taking action. And it’s this lack of action from leadership that led to the diversity and inclusion initiative that I led at Capital One, that the staff were like, you guys all look like deer in the headlights here. That’s not enough for us. It’s not going to be enough for any leader to continue to show up that way. 

If you want some credibility as a white guy, you have to be able to be honest with yourself about your privilege and I’m still working on this. I mean, it’s a path that never, I think, really ends, because it’s so deep and so layered and so complex. But, you and I are design leaders because of our privilege. I think I can confidently say that.

Peter: I can’t dispute it, right? Like I, you know… 

Jesse: Well, let’s talk about, let’s talk about UX as a whole and the early days of UX and the moment at which you and I were engaging with this work, what we did in diving into a new medium, trying to define an unknown field that no one had ever heard of, turning around and trying to sell that to people in power, convince them that it was something that was worth paying a lot of money for, even though you couldn’t go out and get a degree in it. There were no books on the topic until we started writing them.

No person of color could have done anything like that. It would have been way too risky from the start. And they would have had enormous obstacles that you and I never faced in order to get to that place that we got to. 

Peter: I’m, I’m, I don’t have anything much to say because I don’t, I don’t have anything much to add. I think, I think…

Jesse: Tell me about your perspective, like, your experience, like, where has privilege played a role in your career, do you think?

Peter: Well, it’s played a role in my entire life. I remember, it must have been an email ’cause I’m sure my dad wrote it to me. I was in my mid-twenties. Maybe I was living in New York or, after I moved back to San Francisco, and he wrote to me, “it’s great to be young, white, and have plastic,” meaning credit card, with the recognition that as a 24-year old white guy with a credit card, the world was my oyster. Society kind of existed essentially to enable me. And that phrase has stuck with me, because I have never feared materially. And, I’ve just kind of doubtless been buoyed along by privilege that I hadn’t even recognized. 

And there were times when I, could pat myself on the back for certain career choices. My first full-time design job at Studio Archetype, men and women, roughly equal proportions, the senior, most leadership, the CEO is a man, but, like, women in leadership roles, women as executive creative directors.

Studio Archetype was also, being in San Francisco, gender and sexual orientation equity as well, open out gay people in leadership, bringing their partners to work…

Jesse: Studio Verso was the same way. Studio Verso had women in leadership, was led by a gay man. And we had several other queer folk, in leadership roles as well. So, yeah.

Peter: Yeah. So I was like, “Look at me! I chose a career in a field that is like super open and super inclusive!” Pat myself on the back. And it was probably not until starting to go to conferences like the IA Summit, 2000, 2001, and you look around that room, and you see a lot of women, see a lot of men, you don’t see any black people or like two, and then that’s, that’s obviously not right. But I also didn’t do anything about it. I tended to figure, you know, what, we’re an open hearted, big hearted, liberal minded, touchy-feely community. It’ll work itself out. We’re not putting up the barriers. We’re not inhibiting anyone from joining our community. 

Jesse: We’re just waiting for them to show up. 

Peter: You know, it’s early, so, as the crank turns, and things evolve, I’m sure it’ll work itself out. 

Narrator: it didn’t.

You can get so daunted, the issues that we’re talking about obviously are deeply societally systemic, not even specific to the United States, though they’re probably greater here, but we’re seeing demonstrations around the world. And so the next question is what to do about that. Do I engage at a societal level? Do we engage in an industry level?

Jesse: I think that, certainly, there are some of us that are wired for activism that want to be and have the motivation, the interest, the acumen, the wherewithal to be active change-makers at a societal level.

And God bless those people cause we need them. We need lots of them. But there are lots of roles to play in this. And all of us, I think, have to continue to look at ourselves, continue to root out the racism in our own makeup. To notice when we are contributing toward these systemic effects. 

Here’s a great example, actually. I was reflecting on my time at Adaptive Path and we did not have many people of color at Adaptive Path during its lifespan. We were much better on gender equity than we were on any other kind of equity within Adaptive Path. 

But when I was at Adaptive Path, I hated the idea of myself as this creative director who was going to present all of the teams’ work to the client. And so one thing that I was always doing as a project team lead was orchestrating our client presentation so that everybody got to present their own work.

So, everybody got practice in presenting. So the person who was closest to the work, had the opportunity to speak to it. And so if you knew that you were presenting the work, you were also thinking about, how you were going to talk through your ideas. And what that meant was I was sometimes putting very junior people in front of very senior people and telling them, “It’s okay, you’ve got this.

It’s all good. I’ve got your back.”

But I was not taking into account the way that these kinds of dynamics and the past histories that those designers brought to those experiences might have affected their ability to show up and be successful. I put some people in over their heads by not acknowledging the fact that their status changed the dynamic.

It was not the same as me as a white guy, just showing up and presenting the idea, similar to the founder privilege that you were talking about a few episodes ago.

Peter: I don’t have much to add apart from, looking back at Adaptive Path and, frankly, feeling a little ashamed at the lack of racial diversity. I’m trying to think if we had, I don’t know if we had any, at least in the design staff, Black or Brown folks, some of the administrative, back office folks, yes, but, our designers were largely white as the driven snow. And that’s been a challenge even since leaving Adaptive Path. I never until very recently made diversity and inclusion priority in my work. I would hope fairness in the process would lead to equity in the outcome.

Jesse: Yeah. And that’s a trap that I think a lot of us fall into. I think it’s a very comfortable, safe thing to fall back on to say, “If my intentions are good and I stick to those intentions that everything is going to work out in the end.” And the existence of systemic racism is proof that that is false.

Peter: Right, right, right, right. Totally. There’s two things I’ve learned, which are hard for me because the ways I’ve been successful in recruiting and hiring are: I have a big network. And I a nose for talent. And two things I have learned are, if you hire only in your network, you’re not going to provide access, you’re constraining access.

And, if you rely on your intuition to guide you through choosing candidates, you are subject to your own bias. And, learning how to still tap into that, which allows me to succeed, but recognizing that I need to do it in the context of some of these structures that hopefully remove the bias that I bring to the situation. That has been a challenge. You know, I’ve gotten to appreciate bureaucratic HR recruiting and hiring approaches, which exists mostly to cover the ass of the corporation. But, done right, also should be providing fairness for candidates. 

Jesse: Well, and I think that this is similar to the trust thing in that it’s something that can’t just be addressed at the level of systems and processes and all of the machinery that HR creates to try to prevent these outcomes from happening. It can’t just be about that. It also has to be about how you conduct the interviews, how you, as a leader, approach engaging with people of color. If you have a hard time engaging with people of color, you’re going to have a hard time leading them. 

Peter: Right. 

Jesse: And at some point you do, I think, just have to double down on it and say, this is going to be a priority.

 Music break

Jesse: So at Adaptive Path, years ago, we did an event which was not an event that I had programmed, but I was attending and at the end of the day, I was speaking to some attendees and they talked about the fact that every speaker on the stage that day had been a man. And I looked at the program and I was like, what happened here?

And there were women speakers on the overall program, but they were later in the show. They were not on the opening day. And I was pretty angry, honestly, that we had not caught that. And at that point, going forward with the events that I programmed, I made gender equity on the stage of priority. Despite the fact that I had a series of event managers, all women, who would, complain about the ways in which I was slowing down the process and creating more work for them in seeking out that equity. I just felt it was necessary and worked very hard, for UX Week, for the last several years to create that, and got very good at patting myself on the back for it, and completely had my blinders on to the people of color issue. I would say, you know, it was great anytime we had managed to find a person of color to come speak. That was awesome. And, I was grateful to see it there, but I never prioritized it.

It wasn’t until the final year of UX Week that, in conversation with some of the folks I was working with on the programming, that it became clear to me that this needed to level up to the same level of focus for us as a programming team. And that last UX Week, honestly, is the brownest panel I’ve ever seen at any user experience conference.

Peter: Yes, definitely, thinking a little bit about Adaptive Path, I actually want to give a shout out to one of our co founders, Janice. So of the seven founders, one of them was Janice Fraser.

Janice wrote one of the things that I’ve taken, probably, myself more away from, and maybe it’s as a white person speaking to another white person, she’s helping me think about how I’m showing up. And, so she wrote this post on LinkedIn, June 6th, and basically what she was able to recognize about herself, and I think this is true about me as well, is that it’s easy to try to come across as an ally. You say the right things. You put a Black Lives Matter icon on your Twitter feed and you use the hashtag. But to really commit, to really make the effort to de-center yourself in this conversation can be hard.

And I think what she hits on is part of the reason about that is simply fear. She has a line here: “I was selfish because I was so, so very afraid.” And I, when I read that, that struck me to my core. I know I can be quite selfish in my practices. As a primary breadwinner in a household, I seek opportunities to speak, to write, to be exposed, as a way to support my business and thus support my family.  And there’s a selfishness to that, because, I’m afraid if I don’t continue to get speaking opportunities, my star will decline. The phone will stop ringing (no one actually calls me), the emails will stop coming in, and I’ll lose part of my livelihood. And, I can intellectualize that that is likely not true. 

Jesse: Hmm. 

Peter: I’m almost 50. I’ve got a moderately successful book. People will still pay attention to me. Yeah. People will still pay attention to me, but one of the things we have to overcome is that there seems to be a human condition, that your gain is my loss. There’s somewhere in our psyche, the zero-sum-ness. And I can occasionally find myself feeling that when I reach out to a conference organizer and say, “You’re programming your event. I would love to take part,” and they respond, “We have our fill of white dudes,” and I’m like, “But you didn’t reach out to me before you filled up with white dudes!”

And I get it. I can intellectually understand it. And if I was in their shoes, I’d probably do the same thing, much as the same way you discussed, in programming UX Week. But there’s limbic system, lizard brain, something core, that’s like, “I now feel threatened because I don’t have access to the things that I assumed I should have access to, that I’ve always had access to before. And now I don’t.” And that leads to a fear of relevance, legitimacy, and it’s something I need to overcome, to recognize that immediate gut response for what it is, and how to moderate it. And also, frankly, to be more generous, that’s something that I personally have a challenge with, is generosity.

When I’m invited to speak on a panel, to not jump at the opportunity, but, instead to be, like, “You know what, let me introduce you to other people I know who don’t get those opportunities, who aren’t the first person reached out to when there’s an opening on a panel,” and let me encourage these organizers to consider them. And that’s a change I have to make. And maybe by saying it in this somewhat public forum, others can hold me accountable to that.

Jesse: One thing that comes up on this topic of selfishness is the way that leaders behave when their power feels threatened in some way. And how that can lead them to kind of fall back on these shortcuts, try to hold onto that power, and not maintaining that level of awareness of how their choices are playing out around them. 

I think that, like a lot of the other things that we’ve talked about, this has to be approached as both an organizational problem, and a problem at the level of leaders and their relationships and how they show up day-to-day. You have to be able to address it from both perspectives.

Peter: I guess I don’t want to tell leaders what to do, ‘cause I don’t know what to do. But going back to that responsibility notion, leaders need to recognize, intentionally or unintentionally, how they show up has an impact, but like, doing nothing is not a strategy. 

Being afraid and being aware that you’re afraid, you might think that you’re actually contributing by pulling back. and that’s not how we get through this. Nor is it, though, that you grabbed the mic and tell everybody what to do. 

Jesse: Yeah. Yeah. It’s not one or the other. In fact, I think what you’ve touched on here is one of the most critical things, which is self-awareness. It’s like, how much are you paying attention towWhat you talked about, that gut instinct, that reflexive reaction that you have, and questioning it, interrogating it, challenging your own thoughts. You know, I grew up in the South. There is a raging racist asshole in my brain. I can hear that voice, and the more I listen for it, the more I hear it. And every time I hear it, I can go, okay, that can fuck off. And the more that I do that, yes, practicing that awareness, it’s just like, noticing if you’re meeting a new team for the first time and assuming that, Oh, the young woman at the end of the table, she’s probably the admin, right? Or the junior project manager. It’s exactly that same kind of thing. Only just extending that level of awareness to all of our interactions, in all of our lives, and noticing the places where we take those convenient shortcuts, noting the places where we fall back on what is easy, what is comfortable and noticing where we can change our attitudes, change our perspectives, change our approaches.

Peter: So that about wraps up another episode of Finding Our Way. Thank you for joining us on this journey. Jesse and I grappled with some pretty challenging issues, and not come to any specific resolution, but, I think, that speaks to there’s no easy solution. This is an ongoing process. And so we thank you for joining us as we think through it ourselves, and we’ll continue to do so. 

As always, we are eager to hear what you have to say. You can find us through a number of ways. On Twitter, I am @peterme. Jesse is @jjg.

You can also find us on our website, http://findingourway.design, use the contact form there. We continue to receive emails through that. We read all of them and appreciate all the questions and contributions that people are making. That about wraps it up. So again, thank you for listening and thank you, Jesse, for a good conversation,

Jesse: Thanks, Peter.  Finding our Way.

In which we are joined by Maria Giudice, founder of Hot Studio, former design executive at Facebook and Autodesk, for a whirlwind discussion of her career, design leadership, and coaching.

Topics: Frank Frazetta; Working Girl; art school; white designer dudes; New York in the mid-80s; Richard Saul Wurman telling us we’re all full of shit; designing guidebooks; command-and-control leadership style; San Francisco in the late 80s; becoming a design leader; hiring misfits; match between leader and the team; inheriting teams; the brutality of corporate America; learning from mistakes; change-making at scale; consulting vs in-house; the need for executive sponsorship; where we find joy in our lives; meaning and purpose in our work; leading and coaching in a fashion authentic to you; the value of coaching for senior leaders.

Peter: Welcome to Finding Our Way, the podcast on design and design leadership. I’m Peter Merholz. And with me as always is Jesse James Garrett.

Jesse: Hello, Peter.

Peter: And today we have a special guest, Maria Giudice.

Maria: Hi, everybody. Peter. I’m so happy, you know how to pronounce my last name.

Peter: I’ve known you for, has it been 25 years? 1997. And so, we’re excited to have you with us today. Maria, I think you’ve, as… as we were saying, have a lot of lived experience as a design leader…

Maria: Yes we have…

Peter: I also am interested in your experience with other design leaders, maybe even earlier in your career before you became one. So, you know, I want to kind of cede the floor to you to let you talk about yourself and how you would like to introduce yourself to, to our audience.

Maria: So my journey, boy, it’s like if you look at it in terms of timeline, it’s a lot of years, but the good thing is I always feel like, because things are always changing, it feels like it’s a relatively short timeline in weird ways. Does that make sense? It’s sort of like, that’s the beauty of the industry that we’re in, that we have had the gift of constant change throughout the courses of our career. 

Jesse: You can’t get bored, for sure.

Maria: No, you can’t. So, but when I started out, I thought I was going to be a fine artist. My uncle was a pretty well known fantasy painter named Frank Frazetta, and some people right now who are hearing this…

Peter: I bet Jesse had some of his posters in his dorm room…

Jesse: I was not that guy, but I was friends with that guy.

Maria: Yeah, exactly. Some of your people on your podcasts are like, their mind is blown right now, but most people on your podcast don’t know who he is, but some people it’s like, a secret code. If you know, Frank Frazetta’s work. 

Jesse: If you have any visual memory of the classic poster of Arnold Schwartzenegger as Conan, the Barbarian, Frank Frazetta painted that poster.

Maria: Yeah. So I grew up with a famous uncle who was a painter. And that just was like permission to want to be a fine artist as well. So I never thought of fine art as something that was a nice-to-have. I saw I had models early on that you could follow your dreams and make money doing those dreams.

And in my senior year of college, I was taking design classes. And I was really struggling with design in general. I thought it was incredibly formulaic and I was like, “Ugh.”Iit was all about the Bauhaus, was all about like grids and white space and hierarchy and find a nice image and use Helvetica and wear black and be a white man. It was like, these are all the formulas of what it meant to be a designer. It wasn’t until my senior year when Richard Saul Wurman came in and gave a talk to our class.

And did you guys ever see the movie Working Girl? With Melanie Griffith.

Peter: I have not.

Maria: You should look that up because I

Peter: Melanie Griffith and, Sigourney, Sigourney Waver…

Maria: Yes, I, I was that girl. I was that girl working from Staten Island. Yeah. I did not look like a typical designer. And so I grew up in the era of Vignelli and, Rudy de Harak and like these, the New York, Pushpin Studio. Yeah. Yeah. Milton Glaser. I grew up in that era and those were all men who had basically harems of people, peons, working for them. So first model of leadership, command and control. And it was really formal and you had to look and act a certain way.

But then in my senior year, Richard Wurman walks into our class, who does not look like a designer. He’s short, he was overweight. He had a big scarf and he was cursing up a fucking storm. And I fell in love. I totally fell in love. That was like, Oh my God, this is the first person that doesn’t follow and conform to the norms of what typical design leadership was like.

And he basically yelled at us. He basically said you’re all full of shit. And he talked about design being in service to others. And I’ve said this story over and over again. I don’t think he used those words, but this is my version of the story because It just hit me over the head. It was one of those moments in life that we all have, you can reflect back on it, where suddenly something gets hit on the head and you go in a different path. And that was a very seminal moment in my life where he said the right thing at the right time. And design started making sense to me. That my job, my purpose, was to help people navigate life through the lens of design. And I went to work for him. I graduated college and I worked for him designing guidebooks in New York City. 

I started working with Richard in 1985 as a graphic designer, but it was really a human-centered designer. It’s that philosophy of thinking about who you’re serving and what is the appropriate way to deliver that content? What’s the appropriate medium, what’s the appropriate format, what’s the appropriate way to categorize information? It’s still the same stuff that we do today. It’s the same thinking process. Like, I have not deviated from my thinking process and the way I think about design since that lightning bolt struck me in the head in 1985.

Peter: You mentioned the primary model you had seen was this command and control model. And then there was Richard, what was Richard’s approach to leadership? Was he…

Maria: Command and control, too. 

Peter: So he was a creative director. You were an extension of his brain.

Maria: Oh yeah. Yeah, I remember. I’m rough around the edges. I’ve always been rough around the edges. I was really rough around the edges back then. ‘Cause I had the lack of experience and the nuance and I loved the way he saw the world and the way he looked at information at different lenses and different

categories and different scales. I just was soaking that in. 

That’s command and control style back in the day where you had a creative director and then you were his pair of hands. Right. And I would just argue with him constantly about the layouts, or I would give him alternative layouts. I would redesign the cover and he just would never, ever listen to me. And I just remember at one point sitting in his office, just crying and saying, “You know, why can’t you listen to me? Like, why can’t I have a point of view?” And he just dead-pan looked at me and he said, “Maria, I’m 50 years old,” I was like 25, “I’m 50 years old. Chances are, you are not going to change my opinion anytime soon.”

Jesse: [Laughs]. 

Maria: I accidentally moved to California because he opened an office to redesign the Pacific Bell yellow pages, and I knew that if I didn’t get out of town, I was going to get fired, that, you know, like, our relationship was souring pretty fast, and just so happened that my girlfriend was moving to California and I was thinking, oh, I could do a road trip and hang out with her for six months.

I had no intention of living in California. I didn’t even care about the yellow pages. I was just like, “Free road trip. I’m going to go.” And it was the best move of my life because I went and I worked with a small group of people who had to create the office, which became The Understanding Business.

And it wasn’t until I had distance from Richard, where I had leverage.

Peter: So, how long were you at The Understanding Business?

Maria: I was there from 1987 to 1990, and by the end of the three years, I was a creative director with like 25 people reporting to me.

Peter: So you were now a design leader.

Maria: I was a design leader because I was in charge of maps and then it was like, I can’t do all the maps myself. So we started hiring people and then I became in charge of all the maps. And so suddenly I had a group of people working with me on maps and this is where I first discovered that I was really great at being a good leader. 

Like, if I really am honest about myself, I used to throw great parties. I’m great at getting people together around some sort of purpose and I became really great at motivating and inspiring people to work really hard and believe and hit a high bar of quality.

Peter: You felt, you demonstrated good design leadership. Were you operating as a command and control leader the way that you had seen and if not, what was your mode and how did you develop your leadership style?

Maria: it was totally intuitive. It was really just maybe because I was not like most people. And I felt very intimidated when I was in college by not looking like a white male with good clothing. I felt very empathetic to other people who didn’t fit the format.

I looked for the weirdos. I look for the edge cases. I looked for the misfits. I looked for people who really wanted to learn, had a voracious appetite to learn, had incredibly good, great design and production skills. I cultivated that and I really acted more as a coach and a teacher and collected good ideas.

I never thought of myself as a great designer. I still don’t think I’m a great designer. I think I’m a really good designer. I think I have a great eye for design, but I don’t think that I’m the best designer. So because of that, I cultivated and looked for people who were better than me and I mined for the best ideas.

And then we adopted the best ideas as a collective. So I really was very focused on the collective body of the people that worked for me. 

Music break

Jesse: I think there’s something in your story about the match between a leader and the people on the team. You talk about the way that you were seeking out the people who maybe didn’t quite fit the mold of what a traditional designer looked like, or maybe who didn’t come from the same kind of background.

And I think that if you had inherited a team that was full of those more traditional graphic designer-type people, it would have been much more difficult for you to be successful as a design leader. So there was something about you also selecting for people that you could lead and bringing them into the team.

Maria: Yes. Yes. I had the ability to continue to hire people that I wanted to work with. It wasn’t until I went to Facebook where I started inheriting people. And that’s a whole nother ball of wax when you have to inherit people.

Peter: Well, let’s talk about that for a little…

Maria: Yeah.

Peter: ‘Cause you know, we have some similarities here, like you, Jesse, and I started a consulting business, doing design. We hired people we wanted to work with. We, I think, similarly had our flavors of misfits, which might be different than your flavors of misfits, but still certain misfit personalities.

Maria: We all had our own brand of misfits. They all found their home in the misfit land of agencies.

Peter: Something we’ve talked about before is inheriting teams. I’ve had to do it, after I left Adaptive Path. And, so I’m wondering, what your experience was when you inherited teams at Facebook and then I’m assuming again at Autodesk.

Did you have to adopt or adapt your style or did you just try to get rid of as many of the people who were there as you could and bring in your own misfits, or, like, what’s your approach when it comes to inheriting teams? How has that worked for you, or did it not?

Maria: Yeah, boy, I really struggled. I don’t know about you guys, but to go from like master of your own queendom to suddenly in corporate America where you have to fit into a system, that was a really rude awakening for me. But, I want to jump from Facebook to Autodesk because Autodesk was really interesting in that it was kind of brutal.

And I think this happens a lot in corporate America, where I get hired, and I have to assume that this is the test of a lot of like C-level people. Or, you know, SVP level people. Right. I get hired in as VP of Design and I don’t have like a budget. I don’t have like staff.

Peter: Are you the first VP of design they’ve ever had?

Maria: Yeah, first VP and this is a company that’s rooted in traditional engineering thinking for 30-something years. And I just had an enlightened boss who wanted this change, and also Carl Bass is very creative. So I get in and they didn’t budget me in. Like in corporate America, right, they budget you, you get head count.

So suddenly I get hired and I’m not in the plan. So, an SVP wanted to get rid of his design team. And so he gave me his design team, so basically they moved money from his over to my new org by giving me this design team.

So he gives me this team, which has nothing to do with my mission. This is a product team and I’m in charge of weaving design throughout the company. My job was still unclear at that point. I had a three-month period to define my job, but they give me this group of people who didn’t fit any of the profiles that inevitably what I needed.

So they gave me this team. Woohoo. I don’t have a plan for them. And this is the move. This is the perfect move, Maria. This is your head count. This is the budget you’re getting. In order for you to hire new people, you have to fire the people that you have.

Jesse: Wow.

Maria: Fucking brutal.

Peter: So how do you approach that?

Maria: And I didn’t even know who these people are. Right. But this is what they do when you’re a VP, they want to test you. Okay, let’s talk about, like corporate America, corporate America can be brutal at the top.

So it’s like, okay, how tough is she? She’s going to lay people off. 

It’s true. It’s the same way at Facebook. This is what I didn’t like about Facebook. Facebook considers it an act of strength when somebody is struggling, they feel like you are a strong leader, if you can get rid of the weak people, right?

Peter: Up or out, is what I’ve heard. 

Maria: And that’s true. You’re only as good as your weakest person. We all know that. But give people a chance to grow and succeed. What happens in corporate America, if you’re struggling, they put you on a PIP, right? Maybe you get “meets most” two or three times and you get put on a PIP.

Right. But once you’re in “meets most” you’re basically feeling so unconfident, you’re feeling like you suck, you’re in the dog house when you’re in “meets most.” So your mindset is already in this really low point. And then it’s like, fuck you, corporate America, here’s the list of things you gotta do to pull yourself out. And if you don’t do it, we’re gonna push you out. And it’s a sign of strength when the leader can push those people out. It didn’t sit with my values. It doesn’t sit with my values.

Peter: I hear you. I’ve inherited a few teams and, I’m not the only design leader who’s inherited a team and had either your boss tell you or your peers tell you, part of the job is going to have to be managing a couple of these people out that are underperforming. And you’re like, why, why did you wait–?

Maria: Passing the buck to you, right. Passing the buck to you.

Peter: But what I often found is that the designers that I inherited were often capable, but they had been put in a context that, that didn’t allow them to be a good designer. So it wasn’t about the designer. It was about the stuff surrounding them.

Maria: Exactly. And that’s how I feel like you got to really unpack why somebody’s not doing well. Sometimes, it’s not a good skill match, but sometimes it’s because they had a shitty leader who, like, knocked them down. But in Facebook, if you don’t push that person out, you are considered weak.

And it really killed me because I wanted to give those people time to. Evolve or if it wasn’t a good match, what is a better humane way to give them dignity and get them out on their own timeline? 

Peter: Let’s rewind a bit then. You ran hot for, what, 15, almost 20 years? How long did it last?

Maria: Over 15 years 

Peter: 15 years.

So you then had Richard Saul Wurman as a model, good or bad.

Maria: Yes. Yeah. Good and bad. 

Peter: Then you went out on your own (good or bad). Then you went out on your own and you were intuiting your way through design leadership and, and, I’m assuming largely self-taught. 

And then, you know, Hot gets acquired at Facebook. You’re there for a couple of years. You’re at Autodesk for a couple years. You’ve clearly had some challenged experiences, but I’m wondering coming out of Autodesk, you know, those four to five years in corporate America, what did you learn that you were able to take away and actually grow from?

Maria: Yeah. Great question, Peter, because, and, you know, my exit at Autodesk, wasn’t, like, lovely, right? I was kicking ass at Autodesk and making great change at scale. And then there was a change in leadership. Carl Bass steps down, my champion steps down, a new leader comes into place and basically tells me to my face that I’m in the wrong place at the wrong time.

He basically said, “We’re not ready for somebody like you. You’re Autodesk three years from now.” The things that I care about were not their priority. 

Fair enough. But it hurt. But it gave me a lot of time to self reflect. Like, what are the lessons? What are the opportunities? What were the things that I did really well? What was the things I really fucked up because really, I was so ill-prepared for corporate America and I made so many mistakes. And then when I got to Autodesk, I was like, I’m not going to make those mistakes again. So I made a list of all the things I fucked up and I was like, don’t do those things at Autodesk, do the opposite. Right. But now, like two years at Autodesk, there was a whole bunch of things that I fucked up that I could reflect on.

And so this got me really passionate about change-making at scale, that there are people like me who are entering companies at the VP level, they’re told that their job is X, but their job will really be Y. There’s no playbook for being that person.

So I started getting curious and I started interviewing design leaders, VPs and above, and I’ve collected like 25-30 stories from people in all different industries. And now I’m ready to write a book on change-making at scale. I speak about it.

It led to coaching. I want to bring these lessons to light so that somebody like me who is entering a new company could read, and better prepare for the change that will inevitably hit them. And so there’s tons of lessons there that I want to share, not only from my own life experience, but the people who are living it now.

Jesse: I’m interested in this idea of change-making because I feel like for my entire career, I have been, and Peter has been in, you have been constantly driving change in one way or another. We’ve been a part of this wave of digital media and the internet and all of the evolution of user experience design that has sprung out of that. 

And I find myself wondering, like, are we condemned to forever be change agents? Or does user experience design at least get to some place where somebody coming into an organization as a design leader no longer has to carry the assumption that they’re going to have to do a whole bunch of change-making work in order to be successful.

Maria: Really depends on the maturity of the organization in terms of how they’re embracing design and human-centered design. Most companies, design is not part of the culture. Design is a new phenomenon that people are learning about and embracing and this was where I got very cavalier. It’s like, Oh yeah, I’ve worked for hundreds of companies over my 20 year tenure, working in an agency.

It’s nothing like when you’re inside a company, because when we’re working in an agency, people are hiring us to do change. They know time is money, we like basically go in and have sex and leave. We don’t stay the night. We’re like, that was great. Get the clothes back on, go home, sleep in your own bed. Right.

When you’re inside a company, you are living in the house  

Music break

Peter: I want to pursue one thread there. You were brought in by a CEO at Autodesk, Carl Bass, who recognized it.

Maria: Yes.

Peter: Now, most people are working at companies where the CEOs don’t get this. So do they have any hope or are they…

Maria: Are they, are they fucked? Are they fucked?

Peter: Are they, like, what is the opportunity for change when you don’t have the CEO providing some cover? Or, and how can you get this? How do you help a CEO understand…

Maria: See, this is the thing, if you look up and you don’t see people who believe in your agenda, you are pushing water upstream. You need somebody at the high levels or you gotta look for those tradition holders, those people who’ve been in companies a long time who have some cache and power. And if they can believe in it and give you time. 

If you look up and you don’t have somebody who believes in your mission, that is a huge red flag and it may not be worth your time. So you have to really decide, are you at the right place at the right time in your career?

I’m an executive coach and I spent a lot of time helping people. Figure out that they have to quit their job.

Peter: Oh, that one’s tough, right? ‘Cause we all need jobs. You know, when Jesse and I were younger and maverick and running Adaptive Path and we’d speak at conferences or hold our own events and we would talk about the glories of good UX practice and inevitably someone would raise their hand and say, “There’s no way I can make this happen in my company” or “How can I make this happen in my company, ‘cause conditions aren’t allowing it.” And I was the glib privileged white dude who was like, quit, get a job elsewhere.

Maria: Yeah, I know. Yeah. That is a very privileged place to be. I always ask people, “Why do you have your job? What’s important to you. What brings you joy? How can you bring joy into your life?”

Some people bring joy into life after they leave their job. Some people say, “There’s enough there for me to be interested and I’m going to go and leave. And I’m going to paint for three hours a night.” That’s valid. You have to find your purpose in life, and figure out what are the baseline ways that you need to survive. 

So you can’t just say, “Look, you hate your job, quit it.” Some people can’t, okay? But then what are some other mechanisms that you can do to bring joy into your life?

People might say, “That’s my job. My joy is my children.” And then I would ask, “How can you bring joy into your work life?” So that it’s not something that you hate going to, and I knew that I was not happy at Facebook because I was so happy when Friday came along and I was so miserable when Monday started. 

Jesse: Telltale signs. 

Maria: So I had to cope with being in a company that wasn’t really congruent with my values. Was it the right move? Absolutely. Was I prepared for it? No fucking way. 

Jesse: Well, I think that we’re all looking for our right fit, right? Regardless of where you are in your career, whether you’re a designer or a leader, designers are looking for leaders who are going to be the right fit. Leaders are looking for people to join their teams who are the right fit. And they’re looking for larger organizations to be a part of that are the right fit. 

Maria: Yeah. So you have to really weigh everything and you have to find the joy because life is short. Life is short. If you are waking up every day miserable, you have to figure out what do you need to change in order to bring some joy into your life, some purpose and meaning, and you might not get it from your job. And that is okay, but that means you have to get it somewhere else.