In this episode of the Acima Development Podcast, Mike kicks things off with a humorous comparison between the DMV and employee onboarding, using the DMV’s predictability as a metaphor for what onboarding should feel like: smooth and well-organized. The team, including interns Chloe and Jordan, along with veteran team members like Will, Matt, and Tim, dives into the realities of onboarding experiences. Chloe and Jordan reflect on the value of strong documentation, access to multiple mentors, and feeling emotionally supported. They emphasize how overwhelming onboarding can be when information overload hits or support is unclear, and how even small gestures, like developer lunches or Slack channels, can make a big difference in building comfort and connection.

The discussion expands to include insights from more senior voices like Will and Matt, who underline the psychological and emotional complexity of onboarding, particularly for seasoned professionals used to excelling. Will points out that new hires, especially mid-career professionals, often face an identity crisis when they’re suddenly inexperienced again, and that trust between leadership and new employees must be earned, not assumed. He stresses the importance of proactive communication, asking questions, and building relationships over time. Meanwhile, Matt emphasizes that leaders must take responsibility for initiating that trust and creating a culture of safety and availability, even if time and organizational bandwidth are constraints.

Finally, the group turns to strategies for remote and global onboarding, with Tim detailing Microsoft’s best-in-class processes that pair automation with strong support systems. The consensus is that technical logistics like IAM provisioning and documentation matter, but they’re not enough on their own. What truly shapes a successful onboarding experience is human connection: pairing new hires with mentors, creating safe spaces for questions, recognizing cultural differences, and setting realistic expectations. The episode closes with a collective realization that while automation can streamline processes, it’s trust, empathy, and communication that ultimately empower new team members to thrive.

Transcript:

MIKE: Hello, and welcome to another episode of the Acima Development Podcast. I'm Mike, and I'm hosting again today. We've got a good crew here today. We've got Tim, Kyle, and we've got a couple of interns who are joining with us today¬¬—Chloe and Jordan, great having you. I’m excited to hear your input. It's very topical for today. We have Justin and Dave, and, finally, Will Archer, the crew here. I think I got everybody. Did I get to you, Kyle? I think I mentioned you. If not...[laughs]

Let's start with an ordeal I'm going to have to go through in the next couple of weeks. So, it's been five years or so since I last renewed my driver's license, so I have to go to the DMV next week [laughs].

JUSTIN: I want to see how you're going to tie this together with new hires. This is going to be really entertaining.

[laughter]

MIKE: People do not look forward to going to the DMV. There's an old song that comes to my mind that says, "I've been to hell. I spell it DMV [laughs]." I think of that every time. I went and looked up the lyrics. There's some other lyrics in that song I'm not going to share [laughs]. I'm going to point out the reference. But it makes a point that I think most of us tend to agree with.

However, when I go to the DMV, I know exactly what to expect because they have done this a million times, right? Maybe literally a million times, maybe more than a million, you know, many millions in a large state. They just do this over and over again. So, they have a routine. I know I walk in there. I'm going to get the number, and then they're going to send me down to a seat and wait for who knows how long [laughs]. They might have one of those little counters to let me know when the number is coming.

At the one DMV I would go to, there's, like, three different desks, so there's actually three different lines [laughs]. You have to know which one you're getting to. But they have signs. They've got tape on the floor that sends you to the right direction. And then when they call you up, they've done this so many times that the people there they don't even, like, see your face anymore [laughs]. They just walk you through the routine.

And it's so standardized because they need to make sure that it always works every single time. And it generally does [chuckles], as long as you didn't forget to bring whatever document you needed to bring, and then they send you to the back of the line or send you home [chuckles], and you have to come back. If you get everything right, it just works because they've totally standardized that process.

Now, it's totally impersonal, and [chuckles] you wait forever sometimes, and nobody likes that. I have heard that they've got, like, some...There are offices in Utah, and I've heard that they've got, like, some express DMV out there that works really well. I've heard some people say some good things about that. I'm seeing some nods out there. Because they’ve cut the process...streamlined so you can go in there and just take care of that part that's fast, and they run you through. If you set up an appointment, you go right through.

So, it actually can be pretty good when you have everything lined up and planned ahead of time. I think that we've all been involved in starting something before that did not go so well [chuckles], when things were not planned, and it can be an absolute disaster. We're going to talk today about onboarding new employees.

And I bring up the DMV because if you have everything lined up, you might not enjoy it, but it'll be relatively fast. You're probably not going to be there for a week [chuckles], and they will take care of your needs, and you will leave with your business taken care of. And sometimes when we onboard new employees, it does not go like that at all. I've seen some horror stories where people did not get their computer for a month [laughs], and...I’ll work someday, you know [laughs], and nothing goes through. It can be a total disaster. And somehow, we've been doing this for however many decades we've been doing it in software, and it still takes...it's still hard. It's still hard.

That's what we're going to talk about today. We talked about onboarding, actually, about a year ago. You can go back, and I think it was July of 2024. We talked some about this. And that time, we focused a lot on the mentoring aspects of it. Today I thought we'd talk a little bit more...to have a little more opportunity for horror stories [laughs] we’ve seen. And we've got some people who've recently onboarded. We can talk about the good and the bad. And we’re going to talk about a little bit more of the hands-on, nuts and bolts. How do we make this work?

So, I would like to start by asking our recent hires here [chuckles], so Chloe and Jordan, what went well, and what did not go well about your onboarding process?

CHLOE: I can start. I feel like one thing that went really well is there was a lot of documentation, so a lot of really good resources to get help when it came to onboarding, as well as I was paired with somebody who has recently onboarded just a few months prior. And so, they had a lot of really fresh experience as well as advice when it came to onboarding because they had just done it, so they had already kind of figured out a lot of the things that could go wrong or any problems that I might have encountered.

Something that was a little bit more challenging was, I think, when you are onboarding, it just feels like you are in a pool of water, and there's these big waves. And it's really hard to feel like you can catch a breath and feel like you're understanding everything, and that's common to a lot of places. But it feels like there's so much to learn, and you always feel behind, which is a tough feeling to feel when you're coming into a new company.

MIKE: Great. Thank you. Jordan, any thoughts from you?

JORDAN: Yeah, so this is, like, something that is kind of obvious, but I think good documentation is a must. And this isn't any fault of the company, but maybe of my own from last year. Since we started the project, there's very minimal documentation for it [laughs], and it's simple enough where you can get it figured out. But I think that was a little bit of a struggle trying to remember what I did and asking some people, like, “Did I do this right?” So, there's that.

But something I thought was helpful was having some early low-hanging fruit tickets that got ready for us, basically. He had chosen them and said, “These are good tickets for you guys to kind of remember what you're doing or learn how to do things again,” so that was very nice.

MIKE: Nice. Well, thank you. Now, we've talked to you all who just recently started at Acima. But we also have some others here on the call. Will has recently started a new position, so I think he's got some fresh onboarding stories in mind as well, and I think some others as well. So, go ahead, Will.

WILL: Well, I've onboarded a lot, and I think, like, oh gosh, like, I'm getting through it. I mean, part of it, like, the biggest thing, I think, to keep in mind is you're just going to have to embrace the suck. You know, like, it's going to be bad, and it's always going to be bad. There's no comfortable way, I think, for, like, ordinarily high-achieving people who are used to not looking like an idiot to be real dumb and real helpless and completely ignorant for a period of weeks, if not months. There's just no...you know what I mean? Like, there's not a lot of, like, C minus students [laughs] getting onboarded, but, like, you're just going to have to take...you're going to have to take a bunch of Ls.

And I’ve sort of, like, as I look...so, I mean, like, having done it, I always find the process really, really rewarding when I'm through it. But I have to remind myself, like, “This isn't supposed to feel good [laughs]. This isn't supposed to feel good,” at every point there. And so, if I'm reminding myself, like, as I'm through it...because, like, it's me and a buddy. We both came in here. We got recruited at the same time, and sort of, like, we're both sort of our support group, right? Because, like, I'm extremely old, and I get hired on because people expect me to come in, you know, plug and play. Like, I'm expected to produce.

I'm not an intern, and there is, I mean, like, I think everybody is understanding, but, like, there is a certain level of expectation that I have to, like, get things done. And so, like, me and my buddy are just sort of...we're constantly reminding each other: you need to be vocal. You need to be out there, like, asking questions. You need to be bringing people in. You need to be sort of getting on pairs. You need to be proactively searching out documentation and following it and not being surprised when it's wrong because it's frequently wrong.

And you need to be aware of asking questions in the right way, where, like, if you're asking a question, you need to be doing the work. You need to be visibly working harder than whoever you're asking a question of. You need to be sort of, like, cognizant of chain of command, whereby you go up to your team lead, and then you go up to your manager, and maybe you go up to, like, a staff engineer, a principal or whoever, and then, like, if you've got to go...if you have to go to a director, you can go to a director, and I will.

But I'm not going to go there without the checklist filled out where it's, like, I would do this and this and this and this and this, and this led me to you. This is what I'm trying to do. This is the problem, and this is what I need you to sign off on, right? And then, as you do that, eventually, the sun will come out, you know, come out through the clouds, and you can start getting things done, and you're not going to piss too many people off in the process. I don't know. Sorry. It was a vague prompt, and I'm trying to distill, like, you know, what to do, right [chuckles]?

MIKE: Will, you and Chloe both pointed out something that I think is really interesting. You both talked about from the perspective of somebody who's being onboarded and said it's hard, and Chloe swimming against those waves [chuckles]. And you talked about, you know, you're just going to feel dumb, and that is hard. I’ve worked with --

WILL: You're going to be dumb [laughs]. It's not a feeling. You suck [laughs].

MIKE: Well, I've worked with...I've seen a number of people who switch careers later on, and some of them really, really struggle because they were successful before and now they're not, right [chuckles]?

WILL: Yeah.

MIKE: They're the noob, you know, they don't know what they're doing. And they are making mistakes, and they can't figure things out. And they feel like everybody knows this better than them. And that is not a good feeling. But you have to just embrace that for way longer than is comfortable if you want to be successful. And you have to say, okay, yeah, I'm back in high school. Maybe I'm back in junior high [laughs], and I just have to live that role again.

WILL: Well, man, I think...I don't know. I mean, this is maybe, like...this is not an intern problem. Like, you guys have been dumb recently enough that, like [laughter], you can still remember the feeling and cope with it. But, like, I'm 45 years old, and I've been good at my job for a very long time. And, like, imagine, like, going back to school, going back to high school and, like, not doing great [laughter]. But I feel like that's a trap. I feel like it's a trap that later on in your career you can get trapped in, later on in your life, you know.

Like, you could get into your mid-40s and be like, I always wanted to learn, I don't know, basket weaving or, like...you know what I mean? But, like, I'm so good at everything else in my life. If I go and do this thing, you know, I wanted to learn ballroom dancing and, like, I'm bad at it. And there's no skipping over that first...that first rung of the ladder. You're just going to be bad at it. So, you're going to either figure out a way to, like, embrace stupidity later on in life, or you're going to stagnate, and that will just be...you'll just be stuck forever. And I think that's --

MATT: We've all gone through it, right? And we still do, regardless of our level. You talked about going up through leads, managers, staff, principals, directors. I'm currently a director with a company.

WILL: I'm sorry.

MATT: And I still go through it. We don't always know everything, and we're always going to need some help. Part of it is just accepting that and understanding that everybody goes through it. Other people go through it, and more likely than not, they're going to be willing to help you through it. So, go in with that mindset, and I think you'll do all right.

I don't require someone to go through all of the chains of command to come talk to me, at all. If it's something really trivial that they could have leaned over to the guy next to them or the girl next to them and got an answer really quick, then maybe I'll say, “Hey, did you ask these guys at all?” But door's always open. You need help --

WILL: Yeah, but they don't know that, Matt. They don't know that. They don't know you. They don't know who you are.

MATT: Yeah, it's my responsibility to make that clear, right, and, hopefully, I have with Jordan and Chloe, you know, as I’ve talked to them over the time they’ve been here but --

WILL: I’m going to lean back on that one, Matt, because it cannot be done. Like, what you’re talking about, you could say that, and you could say it clearly and effectively, and you could say it with clarity and confidence. You can say that in that sentence, right? But, like, you cannot establish that level of trust in a 15-minute getting-to-know-you meeting. Like, that has to be grown over time.

You can't just be like, “Listen, my door is always open.” And I'm more open, and I'd say, like...you know what I mean, like, most critically, I think virtually everybody, you know, at a director level or VP level, like, if you reach out to them and you need help and they can help you, they'll help you, but you got to get on their calendar. And the reason you go through the chain of command is, like, A, you know what I mean, like, yeah, don't waste your director's time; don't waste your VP's time. But also, B, you know, that pyramid gets pretty narrow towards the top, like, you know, you can't be on your calendar just at a whim. But your team lead, yeah, man, if I need five minutes from my team lead, yeah, they better give it to me, you know [laughs], like --

MATT: Yeah, and that's fair. That's fair. Calendar can certainly be tough, you know, it's generally booked all the time. But the way you earn that trust is, try me. You know, you have something you need to talk to me about; you want career advice; you want software advice, try me. And if I don't give you that time, then that trust isn't earned, right, but if I do, then we can establish that rapport. And, yes, it does take a little time to build it, but that's how you do it.

WILL: I don't know, man. I think you have people for that reason because that trust is something that is built over time. You don't have...you can only...what is it, the Dunbar's number? You know what I mean? Like, how many relationships can you maintain? Well, you got to have...that's why you've got people to build that trust among, you know, people that you can't meet with every day or every month, really, you know? It just can't be done.

MATT: And that's correct. You know, it's much easier as you're down the pyramid because the bandwidth is there, right? But ultimately, trust comes from the top. If I can’t trust my leaders, then I don't want to be wherever it is I am.

MIKE: There's something there to be said about the leaders making themselves genuinely, like, doing something to make themselves a little bit vulnerable, like, oh, hey, I can trust you. You know, the thing that, you know, the dog rolls over on its back, shows its belly. And, like, oh, I could hurt you, but I'm not going to. It's giving the opportunity to be hurt so that you know that, hey, I'm here, and I'm not here to hurt you. And the person in that role, in that leadership role has to do something like that, reveal a little bit of vulnerability, and that's, you know, that's just part of relationships.

They still have limited time. That calendar is still going to be limited, no matter how much they do that, and that's a challenge. And you're a new person. You're that new person. You say, “Okay, here's somebody I can go talk to three weeks from now on Tuesday at 8:00 a.m. [laughs],” and that's a problem. So, you're going to have to be assertive with the people closer to you.

MATT: Somebody --

MIKE: Go ahead.

MATT: Yeah, somebody once said to me something that really struck a chord, and that is, we all have time; it's, do I have time for you?

DAVE: Don't say, “I don't have enough time.” Say, “I have too much to do.” Because you can't give yourself more time, but you can reduce the things you've committed to.

MATT: Yes, you can rearrange your schedule because we have time. We have 24 hours in a day, every day. So, it's priority, right? So, am I going to make you a priority? Is my superior going to make me a priority? And that's something that I think we all need to try to do. Sometimes it's not possible because there's other commitments and other people are relying on us, but we can make time.

WILL: I mean, the reason I'm pushing back on this is because you can't. It's a zero-sum game. You can burn yourself out. You can spread yourself too thin, you know? But I think the reason I'm like, no, you can't command trust; you can't command a relationship; you can grow the relationship, but your bandwidth is limited, and you're only going to be able to maintain so many relationships. If you don't respect that process, then you'll find yourself in a trap.

We’ve diverged really badly from onboarding, but I do think there's a point that needs to be made, where you'll go to somebody and you'll say, "Listen, my door's always open. I need feedback. If something's going bad with this project, I need you to let me know. I need reality. I need this relationship to be strong." But then you say that, and you mean it. It's not that you don't mean it, but because you haven't grown that trust, that relationship isn't actually there. And you rely on it, but it isn't actually there.

And then, you can get these really weird communication mismatches. And you can get these really weird things because you said, "Do this thing," and they said, "Sure, boss." But it isn't there, but you think it's there, and you rely on it, but it isn't. It's ephemeral. You have to respect the need for cultivating those things and the limits around what you can and can't do.

DAVE: I think you guys are both right. I'm hearing something interesting from both of you guys. What I'm hearing from Will, and I think you're right, that there's a boundary. You can teach me something, but you can't understand it for me. You can offer psychological safeties, but you can't make me trust you.

But I think Matt is right that you have to get up and go offer it. If you're the training or the onboarder, it behooves you to actually make an explicit, “I have to go do this. I have to go talk to you and let you know that my door...I have to tell you what the culture is, unless I'm assuming that you're weapons grade good at reading rooms,” which most of us aren't. So, I think you guys have both got the right...you can only go up to your own boundary. And so, what Matt is saying, you've got to charge your boundary if you're a leader. You've got to get right up to their boundary. And I think Will's right that you can't go over it. You can't make them take it.

MATT: I totally agree with that.

DAVE: I have an illustration for that, but I figured I would yield the floor.

MATT: There's responsibility and accountability on both sides, right, for --?

DAVE: 100%.

WILL: Kind of, sort of, but not equally divided. Like, if you're in charge, then you're in charge, you know?

DAVE: Scope of power.

WILL: If that reporting relationship is not good and you're a people manager and managing relationships is your primary function or role, then, like, yeah, that's on you.

DAVE: You’re bad at your job.

WILL: It's not 100% you, but it's 80-20, and besides, you know, if they can't do it, like, you hired them, so what? But I'll say this, right? In the context of onboarding, right, because, like, this is something that I don't want to talk out of school. But there are some people who are having a hard time integrating organizationally. And we're bumping up against this sort of, like, lack of trust, which must be cultivated in the chain of command because they need, let's say, resources. I'm trying to be really vague, right, because it's not my story to tell. But they need resources out of the organization. They need, you know, engineering allocations, and they're not getting that, right?

Like, they're like, “Hey, I need access to this. I need explanations of this. I need a...” you know what I mean? “Endpoint opened over here. I need, like, a security review here because, like, I got a hot deadline,” and they're not getting that stuff. And they need to go up that chain of command, and they're running into that lack of trust. Somebody that I know who's also onboarding, and they've been talking to me, right, because, like, we're homies, and we started together. And we're sort of, like, blind men in the dark trying to figure out, like, how this org chart actually operates.

And, you know, I'm just like, listen, I'm just going to email the director because I am a door kicker by nature. And I know that if I go in with good intentions, I will be forgiven even if I do the wrong thing [chuckles], you know? Like, yeah, I've been running my mouth for a long time, and, like, occasionally, I screw up, but I'm always forgiven because I'm not...you know what I mean? Like, I'm not out here, you know, trying to, like, I don't know, take from the organization. I'm just like, you told me to get this thing done, and I'm running into this wall. I’m stuck.

But, like, this is exactly...like, this relationship of trust has yet to grow, and sort of this guy's like, I don't know, “What do I do? What do I do? Nobody's getting back to me. Nobody's returning my emails. I'm stuck.” And not everybody is a door kicker. It's for the best that most people don't think and act like I do. [chuckles] Society kind of depends on it.

[laughter]

DAVE: We can't all be fuel rods. Society would go nuclear. We need control rods between us.

WILL: All gas, no brakes, is not the way to run a functional engineering organization.

DAVE: Yep. All kite, no string. Yep.

MIKE: But you talked about that person getting stuck. You know, I gave examples before of some people who... switching careers later. And I’ve seen people be successful, too. So, like, I’ve seen it go both ways. And the people who are successful are the people who find themselves stuck, and then they go and they ask somebody. And if they don’t get an answer there, they go and they ask somebody else. It’s the people who are willing to do that that are successful because it’s going to happen. You are going to get stuck. It’s inevitable.

DAVE: There’s a really powerful bit of self-help going around the internet these days. I mean, it’s been going around forever, but it’s popped up on my feed, which is that you are responsible for you, right? Nobody’s coming to save you. You are here to save yourself. And yes, it’s wonderful when you’ve got co-workers and managers who will come help you, but this is just your job. You are in charge of your career, and nobody else is in charge of your career.

There are times when getting onboarded or getting the knowledge you need is going to be tough. It’s going to suck. It’s going to be hard. And what you have to do is sit down and go, well, when I started this career, did I think this career would be easier? Did I think it would be hard? No, I thought it would be hard. Okay, well, this is what hard feels like. And that can kind of help you light a fire underneath your breeches without burning your pants off. That’s a weird metaphor [laughter]. But you get what I mean. You’ve got to get up.

And so, it’s like, if you are in that 20% of the 80-20 and you’re not getting that 80, it behooves you to master your 20, to own it, try and get it to 21. And that’s the kind of thing. It might not save your job, but it will absolutely save your career. It’s a tiny, little percentage of investment that pays off over time is take the initiative and go get it. Because if you’ve got a manager like Matt who’s like, "Door’s always open," and Matt has an employee that’s like Will that will come kick the door in and say, "Hey, you closed your door, and I need it open because we need to talk," that’s going to be a good relationship. And it only takes one and a half of you to make that relationship work.

JUSTIN: So, having said, like, just to pivot a little bit, you know, you are responsible for yourself, but as leaders, you know, we’re trying to onboard these folks so that they’re most successful. And I’m bringing this up because, starting next week, I’m going to be onboarding some folks that are very remote. So, it’s, you know [laughter], I want to do what I can to make sure that they’re successful. And we’ve had a couple, you know, I’ve onboarded other folks onto my team, and, you know, so I have a process and everything. But, you know, the very remote is always difficult. What have you guys run into, like, when you’re onboarding folks that, like, you’re not sitting next to, you know, or you’re not even in the same time zone or even in the same hemisphere?

TIM: So, I will steal from what I learned from Microsoft. So, Microsoft, they scale instantly overnight, over a week. They’ll hire offshore engineers for a sprint, and then they’re done right after that sprint for two weeks.

WILL: Woow.

TIM: Or they will hire someone for an epic, which is three months, and then they’re done after that point. So, they have to get their shit figured out. By day two, everything is done and running. So, how do they do that? So, first is, the first step recipe for them is IAM automation. It’s all Entra ID, all automatically driven through Entra ID. And you plug in your own tool, whether it’s Okta, Ping, whatever you’re doing there. That’s the first step: IAM provisioning and automation.

Second is engineering environment setup. Microsoft, since 2014, has had this really cool tool called 1ES, or One Engineering System. And it does exactly what Will was saying in the kind of pre-podcast is, how do I standardize an engineer’s developer platform? That’s what Microsoft does. The One Engineering System automatically gives engineers what they need, and that image, so to say, is built and maintained and automated through their tech leads.

Second is the corporate and security, the stuff that we always overlook that we do within, like, the first four hours, but it’s, you know, it’s really important, kind of compliance policies and conditional access, and signing all the junk.

And then, they have what they call an onboarding buddy. So, they have, like, a 30-60-90-day plan. Someone is always there to answer questions, to help escalate issues. They’re setting goals for those 30-60-90s, and they have what they call buddy KPIs. So, what are you going to be trying to achieve within that period of time? Because engineers thrive on getting stuff from the to-do to the done column. And if it feels like you’re getting stuff done, you still will want to work there.

After that, it’s just like what Chloe and Jordan were saying: documentation and internal wikis. Holy cow, dude. We need it so bad. When I started, my manager said, "Okay, here’s everything that we’ve got." And he just showed me this torrential flood of mismanaged SharePoint folders and Confluence pages that were just all over the place. I’m like, how in the world am I supposed to divine what you want me to learn out of all of this? No idea. So, a well-crafted wiki system is so important.

And then, finally, the analytics and feedback loop, you know, the managers, the HR team, the recruiters, everyone is going to ask you after that 30-60-90 window, “Are we hitting the mark? What are you missing?” Stuff like that. I have never seen an organization do onboarding better, faster, and more efficiently than Microsoft. Those guys are so good at it. But again, that’s just what I’ve been exposed to. I’m sure someone else is probably better at it than them.

MATT: There is one key piece of this missing with Microsoft and how they do it, and I happen to know who their partner is. They also have dedicated teams.

TIM: Yes.

MATT: So, if they need to spin up a team, that team has already worked with them and familiar with their domain and ecosystem, which is why they can move so quickly, and that’s key. However, all of those other things are good, and, you know, everyone should be doing it. But the instant onboarding, that’s a key piece, is those teams are dedicated to Microsoft and only working for Microsoft when they get spun up.

TIM: Because the money’s there, right? They can afford that.

[laughter]

MIKE: You just pointed...That’s a fascinating thing you pointed out there, that the team was prepared to join. You know, interesting, some years ago, when I say some years ago, like, 30 years ago, maybe more than 30 years ago [chuckles], there was a movie that came out. What was it called? Stand and Deliver, maybe, about a teacher who took his inner-city school math class and helped them all pass the calculus AP test. And it was this inspirational movie. Everybody watched it.

And I’ve read some of the back story about that, and they left out...and it’s true; there was this inspirational teacher based on a real person who got his class up there. But they left out something really important. This math teacher had been working with all the teachers in the junior high and in the previous levels in the high school for years, prepping them to teach those students. So, by the time they got to his class, they were already ready, and if you leave out that part, it doesn’t work.

There’s some baseline preparation that you have to have. And it is an inspirational story, but they left out the best part is that he did the work. If you’re going to make this work, you have to do the prep work and lay the foundation. Microsoft, it sounds like they can make this work because they have partners that already know, you know, they’ve got people who already kind of know what’s going on that --

WILL: It sounds a lot. I mean, I love the system, right? Like, they did all the stuff that I just dreamed of, right? I think that’s so cool [laughter]. But at the same time, it sounds a lot closer to, like, an internal transfer than onboarding a new hire, right? It sounds like these are, like, "We’re going to put these assets that have worked with us a bunch and know our systems and stuff like that," and like...Like, oh man, I was twisting arms for a week, literally, to get access to all the Git repos. I was chasing people down.

I mean, in terms of, like, I mean, we can call this directly, right? You’re talking about onboarding India hires, right, or people from Asia, where you’re on the other side of the world, right? I mean, the biggest thing that I have seen people really trip up with, like, these cross-time-zone hires, right? Because it doesn’t really matter. It doesn’t matter so much, like, cross-country, but, like, cross-time-zone, you put people on an island where they don’t have real-time support.

It’s like, I can’t work like that, or, more to the point, I can’t work effectively and efficiently like that, and it’s profoundly demoralizing. Like, if your first two weeks are just sort of, like, sitting there like, [vocalization], I work 15 minutes, stop, wait eight hours for people to wake up, right, like, that’s brutal. I don’t know. I mean, like, I’m pretty good at my job, but I’m not that good. And it’s profoundly demoralizing. And it’s sort of, like, I don’t know. I think it establishes a relationship where, like, you’re kind of, like, you know, you know what I mean? And then, if you treat people like that, then they produce like that.

So, I mean, the thing is, if I could do anything, I mean, and this is not, you know, necessarily good news, but, like, people are going to lose some sleep, you know? Them and you, you know, because, like, you just got to have a block of time where, like, you’re just getting them up and running, you know?

MIKE:  Exactly.

JUSTIN: I really like that. It's like, you can prep all you want, but you got to invest in them for them to be successful. And all the time that you invest in them it's definitely going to cost you something. And you may have to adjust your hours for a while, but it pays off long term. And, you know, whether that's on the front end where you are prepping all the documents and prepping all the training videos and things like that, or it's on your own time where you are, you know, walking them through the application and answering all their questions, and debugging an issue, and walking with them, pair programming through their first PR, you know, all of that is well worth the time to me because, you know, that pair programming time is, you know, it takes up your time, but it enables them to be much more successful.

WILL: Well, I mean, like, a broader thing, but, I mean, like, in all honesty, you know, like, you never really get out of it, right? I mean, like, you could never, you know, I mean, like, if you're going to have somebody on the other side of the world, like, okay, we all know why we do that. But, like, you know, that relationship still has to be cultivated.

Honestly, I've been in a lot of places where they didn't really...I don't know, they're a human being, and they're a human being just like you. And they have the same feelings that you have, and they have the same everything. They're just as smart as you, and if you treat them like an equal, they'll produce for you. And I've seen so many places that just completely...they completely bungle that relationship, and then, you know, everybody knows the horror stories, and, like, I've seen it over and over and over and over and over again.

Because, like, when you, yeah, you're saving a bunch of money, and that's fine, but, like, you're also taking on managing this relationship across this very challenging set of circumstances. And, like, if you're just sort of, like, just trying to save a buck, and you don't want to treat people fundamentally with the exact same amount of respect that you would expect somebody to treat you with, then, like, you know, you're going to get what you get.

MIKE: Well, and you don't save money either.

WILL: No, no, no. No, you do not.

MIKE: Do you know how expensive it is to hire a huge team of people that you then completely ignore and can't accomplish anything for months at a time [laughs]?

WILL: Oh my God.

MIKE: You develop a culture where nobody cares whatsoever because they're not paid attention to. It doesn't matter what they do.

[crosstalk 39:09]

DAVE: They care. They care. They're just caring about the incentives.

WILL: I don’t think [inaudible 39:12]. It ain't your father's India offshore. Like, the developer market in India is competitive these days. If you treat people like a dog, they're going to bail, and if they're good, Microsoft has a shop in India, and so does Google, and so does Facebook. And there are bigger fish than you swimming in this pond, and, like, good people are not any easier to find there than here. Your good people, like, they'll split.

Like, I was surprised at how competitive some place that I was working with before. They were spinning up in an India office, and, like, we had some guys that were like, yeah, hell yeah, like, yeah, this is...okay. All right, I'm [inaudible 40:00]. It sharpened my game up a little bit. This guy is giving me a run for my money. Like, oh, he got a job with Netflix. Bye.

MIKE: You know, I love what you said about treating people as the human beings they are. You can't have an effective relationship without a relationship. It’s not going to work. And I've seen it be very successful working with teams from all over the world. And it's harder the farther apart the time zones are. It absolutely gets harder. Every hour you add to there is another level of difficulty. But if you put in that overlap, are willing to make it work, take that time, it can become a well-oiled machine. And you can have great success with very talented people from wherever.

KYLE: I think, too, one thing that I've had to learn is cultural differences with these distributed teams, right? Yeah, it's easier. Time frame does make a difference. But also, the culture just really affects, like, how you're talking to them and how you might be understanding why they might be stuck or something, right? Because I've worked with teams in, you know, India or in Poland, and they're closer in time zones. But it's definitely different hurdles.

WILL: Oh, man, I love an Asian-European team. If you ever wanted it straight, man, they'll give it to you.

[laughter]

MATT: It's true. We work with some good ones.

WILL: Yeah, wear your helmet, but, like, you'll definitely get that feedback.

[laughter]

MIKE: The cultural differences are a real thing. In some cultures, I have noticed this...we're talking some about India. It's probably not universal, but there is often a hesitance, I found, from some people to speak up, to ask questions because they feel like, oh, I shouldn't be asking people. I should just know this. And it takes some extra work, and good people will recognize that, read the room, like, okay, they're wanting to talk to me, extra work to reach out and say, “Hey...” make it clear that you want them to ask. Make yourself available. Show that vulnerability. Let them know that you're willing to have that relationship. I think that's really important.

TIM: What I learned...and this is coming from someone from Bangladesh who told me, you know, every time you work with a team offshore in these areas, always explain what you want people to do. And it's customary or culturally acceptable for the person who is listening to you to constantly say, “Yes, yes, yes,” to be an active listener. But over at Stateside, when someone says yes like that, it's generally an acknowledgment that I understand what you want me to do, and I will do that. But over there, it's just kind of that unconscious that's how we proceed the conversation forward, not necessarily that --

So, his feedback was, at the end of describing what the task is, ask that individual to repeat it back to you in their own words so that you know the translation, the communication process has occurred successfully. Otherwise, it's almost a surefire recipe for miscommunication. To be honest, that doesn't even have to be, like, an Americanism to another culture. That's probably just good practice for any kind of communication.

MATT: Yeah, that's actually a really good observation, and I haven't thought much about that, but I think it's probably correct. You know, we've been doing a lot of talking, but I'd be really interested to hear some perspective from Chloe and Jordan. A lot of us are leaders that have been talking, and as you guys are coming into this [laughter] career and going through the process, I'd love to hear what your thoughts are. What are some things maybe we're missing that we could help you with?

CHLOE: I can share. One of the most helpful things that's happened since I've been here was, like, very early on, there was a developer lunch. And so, we all kind of were able to go out, have lunch together, and get to know one another. And I was able to get to know one of the team leads (Later that day, we were going to shadow), and just had a very normal conversation. He likes to play video games. My husband plays a ton of video games. We talked about that.

And so, when I went to go shadow him earlier, I felt so much more comfortable asking questions because it wasn't like, this is a team lead that I don't know. It was, oh, this is a person. Because I think, as you guys are talking about how people that we're hiring are people, we should treat them like that, but so are our managers, the leaders in the company. They're also people. And so, I think having that experience made me feel so much more comfortable asking questions, and it didn't feel like the questions were unwanted.

And I think as well with that is, as someone new, I have so many questions, and it's not fair to put that all on one person. Even if they're so well-meaning and they want to answer the questions, they probably don't have the time. So, creating an opportunity where there is a wide range of people to ask questions to helps each of those people not feel overwhelmed. That also helps me not feel like I'm the annoying one asking this one person questions all the time, and also, I get to create more relationships. And so, those are some things that have been helpful, but I think just continuing to have a pool of people for me to go to or for new hires to go to is extremely helpful.

MATT: Do you think, and this is something that we haven't historically done, but what you just said made me think it might be a good idea, do you think something like a roundtable with current employees and full-time staffers would be helpful?

CHLOE: It depends on the nature of the roundtable, but I think, yeah, it could be very helpful of just kind of giving some of that feedback, but also just creating an environment where questions are open, and you can get to know a lot of people at one time.

MIKE: Well, so one thing we did with the interns this year is we identified a group of people, and we're deliberately having them rotate through a pool of people rather than just dropping them on one person like, hey, “Here's your job [chuckles]. Help these people,” because then they have split loyalties, and they don't have time. But having a pool of people they can work with, we very deliberately set that up so they could have a group of people to ask questions to.

I know I'm going to be talking to this lead tomorrow, and this lead the next day, and so on, and then that lead can assign somebody else on their team. So, there's an intent to give structure, to give them lots of opportunities to meet with that group of people and have many people to ask and not just one. I don't know if that's been useful or not. So, I'm curious for feedback on that.

Before I ask, though, one other thing that Chloe and Jordan have done is they've compiled lists of questions, and that was awesome. I've already mentioned that to them. Multiple times...I've been working closely with them this year. I've received a list of questions in a document. Can you answer this, this, this, this, this, and this? We've already explored the options, and now I've got these questions. And that is so helpful because it's a little bit asynchronous. I can go through it when I get a chance. These are well thought out, and it's documented. I can put the answers there. Being willing to get those lists of questions together was actually a really helpful thing.

MATT: Also, something we could share with future internships, so...

MIKE: Absolutely.

MATT: Really valuable.

MIKE: So, back to the question. I'm curious if having the pool of people was helpful. Maybe it wasn't. Maybe it was a failed idea. And I'm also interested in your thoughts, Jordan, because Chloe has shared her thoughts, but you haven't this time. You shared at the beginning, but coming back --

JORDAN: I kind of cheat a little bit because this isn't my first time here, so I know some people.

MIKE: That’s true.

JORDAN: But I think just having a pool of people that you can go to for questions is phenomenally helpful. For example, just onboarding in general, I had multiple people I could ask for different services and all that, but I think being able to know or meet someone is great. And so, I think on the subject of having a list of people that we can go to every day, I think it's very valuable. Having one mentor is nice, and they'll have lots of context on what you're doing and be able to help you very quickly, but that is to the detriment of them not having any time for themselves. So, I think it is valuable to have multiple or even just having someone to help you, so...

TIM: To Chloe and Jordan, I'm curious, would it be more valuable to have a buddy that you can ask for help when you need it? Like, Jordan, you just described, it's valuable, but it could be to their detriment. Or would it be more valuable to be plugged into a Slack channel or a Teams channel where you have onboarding specialists, people who know the questions you're going to ask, and it's a safe space for you to ask stupid questions like, “Hey, I can't get to this. How do I get to this?” Or “I need to submit a ServiceNow ticket. Who do I assign this kind of ticket to?” Which would be more valuable as a newly employed person?

JORDAN: Ideally, both [laughs]. And I say this because having one person that you can ask quick questions to, so you don't have to wait for a random small thing for, I don't know, a couple of hours, is very nice. But, at the same time, being able to document the questions, like the intern chat, was so helpful this year. Like, I came across some personal blockers that, coincidentally, someone else had experienced last year, and I could just go back and read the thread. And if I'm missing some context, I could just ask very quickly to get up to speed. But I think having both a safe space and someone, or people, to ask very quick, simple questions to is great.

TIM: Like the Stack Overflow of onboarding. There's a place you can look for commonly asked questions. Yeah, that's good. I'll be honest, I've been here with Acima for, what, nine months or something like that, and I still will run into things like, where do I send this stupid ticket to? And I debate. I sit there for, like, three minutes. Like, do I put this in general engineering and ask and look like that one guy that can't seem to find that one Confluence page? Or do I just bug someone who's already being bugged [laughs]?

WILL: I love how we keep on looping back to that psychological safety, where it's like, well, I feel bad because I have one person that's onboarding me, even though you have one person that has been specifically selected and tasked to onboard you. And it's like, oh, but I'm asking them so many questions, right? And it feels uncomfortable.

It's totally...like, my point there is not, like...my point there is just, like, this psychological safety and these relationships and bonds and trust and integrating into a community, like, that psychological safety, like, it's so critical. And that is just something that has to be grown. And, as leaders, as people who are already embedded in the community, if you leave anybody with anything, it's to keep that at the top of your mind, and, like, growing that, and, like, being cognizant and aware of its lack, of its absence, right? Because, like, people just...everybody, right?

I mean, you have, like, people who are really senior, who've been doing this for decades, and we're still talking about this stuff, right? Like, me, like, I'm going through it the same way as you. And I suppose, like, the biggest difference is not in how I feel about it, but, like, that I just know that if I do the right things, I'll get the right results. So, I'm okay with, like, my trust fall, you know, into the organization.

MATT: Someone who's really, really good at providing that for people happens to be on this call, and that's Mike. People just feel safe working with Mike. And, you know, I used to report to Mike, and immediately, I just felt that way with him. Because he's there; he's reaching out, and he's making you feel that comfort. And I think, you know, as leaders, we need to be cognizant of that and take an example, right?

And as new people coming on...and it's one of the hardest things to overcome. It really is. That's why a lot of people struggle with paired programming, right? It's the ego, and I don't want to feel dumb. And what are they going to think if I mess up? We need to just accept that we're all human beings. We all mess up, and it's okay. And it's okay to ask those questions, even if it may feel dumb, you know, you're asking it for a reason.

CHLOE: I think I'd really just like to echo that sentiment. I think, coming into this internship, I felt, you know, very overwhelmed because it was in a different language and never had this kind of experience. And one of the first things that Mike said was, “You're not supposed to know everything.” And so, I think that took off the weight.

I think when you're interviewing, you have this pressure of, I need to prove myself that I'm worthy for this position. And then, when you get into the position, I think sometimes we still have that mindset of, I'm still proving myself. But you've got the position, and I think it's an opportunity for you to be, like, it's okay if I don't know everything. I got the position. I'm here. Now it's time for me to learn. And so, I think Mike did a really great job of setting that as the expectation was, I'm not going to know, but I'm here to learn. And I think if we can do that for a lot of people, I think that would help.

KYLE: I would wonder, Mike, you're saying that we've put the interns with a bucket of leaders, or people that they can cross-train with. Have auxiliary teams been included in this? Because do they feel comfortable going to IT, DevOps, security?

MIKE: We have put them with data, but we have not put them with some of the other teams yet. Although I'd love, actually, to have them rotate through some of those other teams. I think that'd be really helpful.

KYLE: Because, yeah, I wouldn't want them to be, you know, I'm on DevOps, and Tim over here is on security. I wouldn't want them to feel timid to reach out to either of us for anything, too.

JORDAN: You know, I think something that kind of happened as a side effect was that we were seated near data and IT, and IT, they're nice, and so they would talk to us. And I think as a result of being able to sit close to them, I'm more willing to go up and talk to them, so I just wanted to point that out.

WILL: [inaudible 55:20] is not all bad [laughs]. Mike wouldn't know [laughter].

MIKE: So, we've talked about a lot of things, and we've been here for a little while. We've talked some from the psychological safety aspect from the leaders. We've also talked a lot about your role as a person being onboarded, that you're going to have to assert yourself a bit. You're going to have to find that way, and you're going to feel stupid [laughs]. That's the reality of doing something new. And that also speaks to leaders. Well, recognize that you've got a bunch of people who are feeling that way, and try to give them the support they need in that very uncomfortable situation, and try to help them get through that quickly.

TIM: I think what's interesting the most out of this conversation, for me, and it speaks to kind of being a little myopic to my role. But every day I fight challenges with automating a lot of the IAM mechanisms of onboarding people, or fighting, how do we get the engineering environment set up, up and running?

But I swear, I think 80% of this conversation has been the soft skill side, the aspect of onboarding, not so much, okay, we get a new employee, and I have to populate a million attributes about this person in our directory, and try to build an automation so that if they have this job title, they automatically get these roles, and stuff like that. That's where my head is at all the time because, in my mind, that is a successful onboarding, that on day one, they have all the roles they need. But when you talk to, I think, employees at large, they're kind of more like, I actually care more about a buddy that's there for me. And I think that's absolutely true.

We hired a person for our team, and it was just to his virtue that I had gone through the same wall that he had months before, and I just had a list of everything that needed to get done because I had just done that. And I think that experience of him being able to lean on me and say, “Okay, what did you do to get things up and running?” I had that list, and that was more valuable to that person as an employee than a shiny system that everything figured out. Which doesn't mean I don't want the shiny system, but I think it's interesting that the human aspect is more in focus than I thought it would be.

MATT: Yeah, I think, and probably true for about every career, but those soft skills, communication, trust, are every bit as important as technical skills.

WILL: I mean, I keep on, like, I don't know, the further I go, the more I think it's more that than anything else. On a technical level, I've had really, really hard technical jobs, really hard technical jobs. But this isn't that. This isn't, you know what I mean, this isn't cutting-edge engineering research.

This is business logic, line-of-business stuff, making sure, you know, I mean, it can be tricky to take a block out of the Jenga tower without knocking the whole thing over, and that can be hard. But it's all about relationships and networks and people and, like, how you get people together to do the job. Like, that is the challenge of this role, not, like, you know, some fancy algorithm, you know, whatever LeetCode may have told you, but you're not going to be doing any of that.

MIKE: No. Maybe if you're a Ph.D. and you're getting hired to do some research somewhere, and those relationships are still going to matter [chuckles], even if you're working on that tricky technical problem, which you almost certainly aren't.

Thank you for joining us, Chloe and Jordan. It's been great having you, and thanks to everybody. It's been nice having a big pool here of people, with everybody contributing and offering different perspectives. It, I think, gave us some really good food for thought, how to do this better, do something that's really hard better.

Until next time on the Acima Development Podcast.