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Episode 45: Interview with Will Larson, Head of Foundation Engineering at Stripe, and Author of An Elegant Puzzle

The Heartbeat Podcast - Leaders share their biggest, hardest lessons learned. | Product Hunt Embed

As Head of Foundation Engineering at Stripe, and Author of An Elegant Puzzle, Will Larson talks about that not all decisions are final and/or permanent, being self- aware, and modeling your behavior in a way that you would like to personify your organization.

Every few weeks as part of The Heartbeat, I ask one question to a founder, CEO, or business owner I respect about their biggest leadership lesson learned. This week, I interview Will Larson, Head of Foundation Engineering at Stripe, and Author of An Elegant Puzzle.

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CLAIRE: Hey everyone, I’m Claire Lew and I’m the CEO of Know Your Team, a software tool that helps managers avoid becoming a bad leader. And I’ve got someone incredible on The Heartbeat today who has spent most of his working life avoiding becoming a bad leader, written a book most recently about it too. So I’m so pleased to have on the show Will Larson who is the Head of Foundation Engineering at Stripe, the payments platform that we’re happy customers of, that so, so many people all over the world are happy customers of. Will most recently though wrote this incredible book which you see all my little index cards here. It’s really that good. It’s called An Elegant Puzzle: Systems of Engineering Management, and actually Stripe published it. It’s a beautiful book. And I could not wait to talk to Will after reading it. I think I also saw you speak, we both spoke at the same conference here in San Francisco, I want to say, earlier this year, as well, and I was impressed from your talk. So excited to ask you this one question, Will, in particular, like I said, many, many questions I have to ask you, but this one in particular. So, you ready?

WILL: Yeah, let’s do it. I’m super excited to answer the question to the best of my ability.

CLAIRE: You bet. The question that I’d love to ask you and that I’ve been asking all leaders that I’ve admired is, what’s one thing you wish you would’ve learned earlier as a leader?

WILL: I love this question. There’s obviously a lot of things that I wish I had learned earlier in my kind of leadership experience. I think I probably could kind of go endlessly long on this.

The first thing I really think about a lot is that I think early on in my career, I thought every decision was final and that things were permanent. So, you’d be having a technology discussion about whether you use one queuing system or another, or you’d be talking about how to design the product that you’re trying to take to market or you’re talking about how to do a small org change and it creates this kind of zero-sumness.

I don’t know, have you read Finite and Infinite Games?

CLAIRE: You know what’s so funny? I have it. I see it on the bookshelf over there and I’ve heard a lot about it, and I’ve talked a lot about the concepts of people but I have not actually read the book.

WILL: The title gives you like 80% and then you can accurately guess the remaining 20% with high accuracy. But I think that idea is so powerful where I used to think that every decision and every choice was zero-sum and I was trying to be right. And then I think this idea where actually you’re just trying to stay in the game together and not lose, but have everyone keep playing together. It’s so powerful. And it took me so long to understand that was when I wasn’t working well with peers, when I wasn’t making good decisions because I thought it was this one-off decision but there are really no one-offs in your career.

CLAIRE: I love that sentiment. I’ve interviewed like, I want to say, over 50 CEOs, founders, managers, executives over the past almost two years now. I don’t think anyone has said that answer before, which is actually pretty rare. Usually they sort of overlap or touch each other, but it’s pretty singular. And I think the reason why I was smiling when you were saying that is because I’m thinking about all the unintended consequences that come from assuming that it has to be perfect or you have to get it right or they’re sort of an answer key in the back of the books somewhere on how to successfully have this team perform well and have a room working well together. For you Will, when did you realize this? I mean, you’ve had sort of a long storied career both at Digg and at Uber in engineering leadership roles. Was it then? Was it at Stripe? Was it previous to that?

WILL: I’ve been realizing this over and over in kind of increasingly clearer ways.

I think one of the gifts of starting to lead in larger roles is that people copy you. And so, sometimes it’s hard to see your own behavior but you see people in your org all start behaving in a certain way and you’re kind of like, “Why is everyone doing this?” And slowly, you walk it back and you realize it’s because you’re doing it and they’re actually modeling this behavior that you’re maybe not as aware of as you thought you were. One of the things I’ve learned about myself, I think to my pleasure and displeasure, is that I’m like a fairly rigid person in a lot of ways. I’ve been seeing that play out in my organization and I’m like, “Wow, why is my org so rigid?” And it’s because I’m rigid.

So that, I think, has become increasingly clear to me as I got into work with larger teams that you can see it much more easily. And so, I think really, it started to be clear to me at Uber kind of this rigidity and the consequences of it and kind of the belief behind the rigidity that these were critical, essential, like bad things would happen if I didn’t get this thing right every single time. And then at Stripe, I got to see the same lesson again and started to internalize it, I think a little bit more this time.

CLAIRE: Totally. I mean, you talk about this concept of modeling actually, there’s a wonderful section of your book where you sort of outline approaches and it’s actually one of the things I was excited to talk to you about. You seem to have done a lot of reflection around your own personal framework for how you think about leadership, which I think is fascinating from a purely sort of academic perspective because you look at sort of the academic field of leadership and management. And my God, there’s like a hundred frameworks, right? And the reason why actually that’s helpful is because sort of the best leaders, what they do is they create the best framework, which is accumulation of a few for themselves. So, I just thought it was so mature and sophisticated in your thinking of sort of formulating your own, instead of sort of like stepping on these sort of other broad frameworks. For example, I think a really popular one is sort of like authentic leadership or a lot of people lean into situational leadership or trait based leadership, et cetera. But the one that you described, it was around, I believe, modeling, documenting, and sharing. Yeah, I’ll sort of leave it there. I’m curious to hear how you got to this and also for you to explain to our audience what this framework is and how it’s useful to you.

WILL: A couple of things there. I think one of the interesting things I think about managing in Silicon Valley when you start out in a smaller startup is that often the role modeling is there’s just like not an experienced manager to model after. And so to your point, you can like read all these books and these books are, I think very helpful. There’s lots of great books out there that I’ve learned a ton from, but they don’t necessarily have like a roadmap you can actually implement. It’s like right here’s how this works at this like multinational corporation or like this is a five person team running out of money, how do I do this?

CLAIRE: Yeah, I mean, I liken it, Will, often to ‘you don’t learn how to ride a bike by reading a book’. It’s like you can read lots of books about it, you can become extremely knowledgeable about the parts and inclines and gears and speed. But it’s a totally another thing to get on it and to do it yourself.

WILL: It’s totally different.

So, I think one of the cool things that happens though is that you actually have this opportunity to kind of reverse engineer what management is. And a lot of times, this goes poorly. So, I don’t think this is the best way we could be training new managers is just kind of throwing the child into the lake and asking them to start swimming, right?


WILL: Sometimes they start swimming but I imagine the success rate is pretty low on that particular one. But it does give you a chance if you take it to sort of think about what management is to you and what resonates and works with you the best way. And I think for me authenticity is, I think, sort of out of necessity. I don’t have much of ability to hide my feelings, getting better at that. But I think authenticity is like a core value for me. And so, I had to figure out what are different styles for leadership that allow me to be kind of true to myself, but that also works because there’s lots of styles that are authentic but don’t work. And so, being authentic to yourself is not like the most, companies don’t hire you to be your authentic self necessarily. They hire you to accomplish something and they’d love it if you could do that in a way where you are authentic but it’s not like [inaudible] of the business is not like Will is his authentic self today or something. No one really cares if I’m authentic to myself on any given day. So, how do you find a style that actually works for you and that you can be kind of fully bought into and engaged with and works for the people around you. And so, one of the styles I found was this kind of model document share, which is this idea that a lot of times you’re trying to make influence but you don’t actually have authority. And I think sometimes you can be defeatist about this where it’s like, “I can’t do anything. I don’t have authority.”


WILL: But I basically never found you have, like no one actually has as much authority as you think they have.


WILL: We’re like, “Oh, the CEO has all the authority,” or so-and-so has all the authority, but everyone’s like living in these tight set of constraints. Maybe you have all this “power”. But the only legal moves you can make from all these constraints, you still only have two choices or you have an infinite authority but you can only deploy it in one or two very simple ways. And so for me, a model document share is like, what if we thought about this without authority? What if we believe that people are going to do rational things and going to do the best thing they can? And if you show something that that works, for example, how you do planning? Or for example, how you do project selection to make sure that not just the loudest folks get access to the best projects? But there’s actually kind of a justice in how projects get assigned across the full set of people who are interested, then you model it and you actually have to show up. Modeling is showing up, which is hard when you’re really busy to remember to show up. Then you document it clearly so other people can find that and then you give them access to that document and kind of tell them about your experience. And I found I’ve been able to do much more through this process because when you work from authority or from central org, you have to do everything so carefully. You have to build alignment. You have to roll it out carefully. But if you have these experiments, “Hey, we did this experiment. If you want to copy it, feel free.” It takes all of the overhead of alignment out of it because it’s not risky. It’s not forced, it’s not mandatory. And then you can see adoption. And we’ve had a lot of success where it did get adopted and then we could just say, “Everyone’s already doing this. Is this just what we do?” And everyone’s like, “Yeah, this is just what we do.” But never having to do the rigid kind of build consensus component that can take up a lot of time.

CLAIRE: Absolutely. I think it’s brilliant and I can see it being so effective. So many of the clients that we’ve worked with have sort of deployed this without even calling it, model document shared, just in the sense that it’s so true for teams and just in human nature that people can’t believe that something is true and works unless they actually see that it’s true and it works. And you can talk all day and you can sort of sit, like you said from your positional authority or whatever sort of title you’ve got under your name on your business card and postulate, “I think we should do this. I know this is sort of the best way to go.” And to prove it out though is a whole nother thing. So here’s where obviously it gets tricky, right? It’s always in the execution of models like this. It assumes a few things. One, that the person is able to model things correctly. Have you as a manager of managers encountered moments where you’re like, “OK.” Like you said, “I saw my team become more rigid because I was being too rigid.” How does one self correct that, especially for yourself as a leader of such a large organization that’s changing rapidly.

WILL: I think there are things where you are intellectually aware of something that you’re not good at or should be doing, but kind of emotionally, or for whatever reason, you just can’t do it.


WILL: For me, something in this category is team building off sites where I know I need to do it. I’ve gotten feedback, I am not doing it enough. The feedback’s correct and I appreciate that it’s correct, but I still just can’t seem to translate it into actual action. And there’s some sort of consistent thing there where some people end up with blocks on certain activities where they’re just like can’t seem to do it. And this one’s funny in the sense that this is like seemingly super doable thing that the vast majority of managers successfully do and that I just consistently bungle in this kind of bizarre way. So, I think there’s definitely things where you know what to do and don’t do it. And actually this is as a side note, like why it’s so hard to interview really senior managers because they know what to tell you, they just don’t necessarily do it.

CLAIRE: Yes. That is so astute.

WILL: If you’re self aware, often you can pair with someone who complements you. And I think you start to be careful about not just the offloading the work you don’t like to someone else, but there are people who like work you don’t like and vice versa where you can actually like be complements. And I think sometimes you can get kind of fortunate with that. But ultimately to lead is to model good behavior. And if you aren’t willing or able to, then you are not weeding well on that dimension and then you have like a portfolio of things that you have to be good at. And I think every leader I’ve worked with has some gap. One of my gaps is definitely team building off-sites. There are others, but it’s not just about being good at everything. Although you do have to try to get reasonable at everything, you can’t be terribly deficient at anything, I think can be a sufficiently good leader at scale.

CLAIRE: Totally. I think the thing that you also sort of illustrate in your sort of in your own answer is you exhibit an awareness of the gap. So I think the problem becomes when the modeling is incorrect but the person doesn’t know that they’re actually incorrectly modeling behavior that is negative for the organization. And what you have sort of beautifully showed is like, yes, you sort of have to be reasonable at everything. There are things that you’re not going to be always great at, but the key is to be able to see that clearly, understanding what you’re modeling well. If you’re not pairing with people, who do sort of lift up the places where you’re not as strong. This is the point that I really particularly resonated with that you said is that essentially what leadership is though is effective modeling at the end of the day. I think a lot of times our conception of leadership for better or for worse, probably for worse, just through our society has been rather a leader more of words, of big bold action, of dramatic flair and charisma. Yet, it’s to your point, sort of the day in and day out, the small, small words of encouragement, the small gestures, small things that people do that they model that that says more than anything,

WILL: I think there are different models of leadership. I think the one you described is one that I personally aspire to, which is I was talking to someone earlier in the day and I think there is this idea that leadership is like as you described it, they’re like having the most dramatic vision, being the most aggressive or the most competitive. But I actually think most of the great leaders I’ve worked with are just extraordinarily consistent at the fundamentals. Actually, a lot of good leadership is just like being an extraordinarily good listener, an extraordinarily kind person, extraordinarily empathetic, extraordinarily consistent in how you do process and how you make decisions. And that it’s not necessarily, to your point, very flashy. It’s just like the consistency when you’re modeling to hundreds or thousands of people, the consistency just becomes, even if you do it wrong one out of a hundred times, that is actually too often at some level.

CLAIRE: Yeah, I love that point. I find that to be so true in so many of the leaders that we’ve worked with. Thank you for sharing that. Okay. Here’s the other thing I wanted to ask you about, Will. Literally, I have hundreds of questions. So I’m like, in my head, picking and choosing which ones am I going to ask because the book was so, so wonderful. I was reading a page where you talked about killing your heroes. Tell me about this. What do you mean?

WILL: That’s interesting. I wrote the majority of the book over a six-month period, but a few of the pieces are things I wrote 10 years ago. That is actually, I think, the oldest piece in there.

CLAIRE: Oh, no.

WILL: That is like about 10 years old. Where was I when I wrote that? I was a few companies ago and we had a senior technical leader who was kind of single handedly trying to prop the company up and like taking it on their back, doing all the work, making all the decisions, dealing with every on-call problem. Every design, they were at the forefront and they were working themselves into the grays. They meant so well but they were also kind of breaking the company while trying to say that. And so, I think so often you kind of lionize that person. Like this is this person who’s saving it. But I think the challenge is it’s both true that this is a wonderful person trying very hard to do the right thing and they’re doing it in such a way that they’re harming the business very meaningfully. And if you don’t stop them, the business will fail to grow at a minimum and maybe like fail overall. And I think that to me is the core of this idea. How do you have empathy for someone who is trying but like sabotaging themselves and others without being angry at them? They’re trying. It’s not that they’re bad, it’s just that they’re mis-implementing, like the approach just doesn’t work.

CLAIRE: Absolutely. Do you think the CEO at the time saw this as an issue or saw this person as a hero and was like, “Thank God, we hired this person,” because maybe I’d have to have hired three people. I think your perspective is spot on, but I also feel like you have that clarity by virtue of your position in some way. You know what I’m saying? I’m curious to hear that. Push back on me if you think that I’m off there. I’m curious what you think.

WILL: We found the 10X engineer and if the 1X engineers just got out of their way, it would all be fine. So, there’s like these myths of productivity. I think as you’re around in tech or the valley long enough, you start to see the public myth, they’re like kind of different projects and individuals and then you talk to people involved and you realize the public myth and the actual experience don’t relate where it’d be like, “Oh, this person who’s perceived publicly to have led this project was never involved,” et cetera. So, I think the perception gap on these things is massive and it’s kind of endemic how big the perception gaps often are and how people’s contributions are erased in kind of complicated ways. In this case, I don’t think there is a whole lot of awareness that this was a problem. Another thing I learned slowly in my career is that if you bring emotion to a lot of disagreements, then people characterize performance problems as relationship problems.

CLAIRE: Interesting.

WILL: And so this is a place where I brought too much emotion into it. And it became, I had a bad relationship with a person versus there was an actual issue because it’s much easier to be clear as a relationship problem with so and so than to actually deal with the fact that there’s something you, as a leader, need to address.

CLAIRE: Right. Absolutely. This leads or sort of segues really nicely to another concept that you talk about that also really hit home from you, which is doing the hard things first but also stopped doing it harder. So like kind of seemingly contradictory ideas that one might say or intention. But I’d love for you just to talk a little bit about both. Just this idea of, I mean, whichever one you want to sort of dive into first. But yeah, stop doing it harder. Curious when you were writing, and again, I love hearing this context of sort of when you were in your career too in thinking about some of these things through.

WILL: Doing the hard thing first, I think that is something I learned doing these larger migrations and I think like technical migrations, like how do we move from this kind of server-based infrastructure to this container based infrastructure? Or how from a manual provisioning to kind of fully hands free automated provisioning or something like that. And so, for the migration article and kind of doing the hardest thing first that the biggest migration I’ve ever done was at Uber. We had this kind of untenable situation where we were getting two or three people a day asking us to set up a service and we were only able to spin up like two or three a week. And so, each day we came in, we were like further behind and we were working hard. You often talk about this idea of being like further behind each day, but it’s rarely trackable in a way where it’s obviously true.


WILL: But the cool thing is we could actually show we were further behind each day. And that’s a cool opportunity because when you’re kind of bankrupt in this specific way, you have permission to re-envision what to do because what you’re doing doesn’t work. So, you don’t have to protect it. It doesn’t work at all. And so for us, we then got to do this automation, this full provisioning pipeline that was self service. And actually, we’re able to completely remove ourselves from it where people could do it instantly with no involvement for us. This then downstream creates lots of other problems that too many services, et cetera. But we fixed the bottleneck, which is like sometimes one bottleneck at a time, you try to fix the overall system or evolve the overall system. Systems aren’t fixable, I suppose. They just evolve. So, that one was I think, how do you make sure you don’t waste work doing things that will never get delivered. And I think that one really resonates with where I’ve seen teams and companies just spent huge amounts of time to kind of no impact. This isn’t just technical, if you’re designing a new process, for example. If you’re trying to roll out a new career level or if you’re introducing the idea of what even is a career level, that also means that there are people who are not at the career level. And how do you handle those folks who have not been at the career level for a long time? Are you going to manage those folks out now? And so, I think using the same thing, what are the hardest edge cases and using that for process design works just as well.

CLAIRE: Yes. I found that to be excellent. And then I thought it was interesting and they’re not direct. They’re not even sort of placed anywhere close in the book. But this idea of stop doing it harder.

WILL: The idea of stopping it harder is more about, I think people try to work through. There’s like the industry conversation about burnout that’s been happening for years. And I think there is this idea that you can work through problems. I think certain problems you can work through. For example, if you have an urgent launch that you need to hit and it’s like two weeks out, you can work harder and be more likely to hit that date. But if you are then every two weeks working harder to hit the next two weeks, you’re just sort of working in a broken system. And I developed this idea at that time of sometimes the only way to fix the system and actually make huge improvements is to let the system fail.

CLAIRE: Yes, I completely agree.

WILL: And I think as a motivated, smart, hardworking person, you can put yourself in spots where you try to sustain the broken system, but it doesn’t work.

CLAIRE: Yup. Exactly. And I think the hard part is distinguishing between the two. When do you let it fail? When do you sort of press on and understand that doing the hard thing first is actually what’s going to save more time in the long run? I think what both concepts actually encapsulate as something else you talk about in the book, which is this idea of focusing on long-term success rather than sort of the feel-goods in the short term and the short term quality, and they are consistent ideas. I just found them interesting because I think on the surface, someone might read it and be like, “Oh, this is like do they play well, do they not?” This is really, really interesting. Another thing you talked about that I actually unfortunately just don’t come across in a lot of leadership literature is you got really tactical about time management. There’s even like a lovely little sheet for [inaudible] of the book where you sort of gave a sample blockout schedule of a potential engineering manager schedule for like one-on-ones and planning that team off site that you’re not really excited to play in. But what advice do you have because I get this question from a lot of different leaders around how you think about managing time. Why it’s so important? What’s worked for you? How has that evolved for you over time as well?

WILL: The reason time management is so important is, I mentioned this earlier slightly. Like a lot of leadership is showing up. And so I think when you think about inclusion and diversity for example, I think there’s like having talking points and there are saying the right things and there are kind of reactively modeling the right behaviors. So there’s like a situation and you uphold kind of the standards you want. And then there’s this next bucket of like spending two hours a week doing proactive outreach, actually investing the time proactively to try to accomplish these. It’s spending time to actually attend like the employee resource groups versus being a sponsor who can’t kind of carve out the time. So I think time management is so important because ultimately as a leader, your values are where you put your time and they’re not really what you believe because there’s lots of things that people believe and support that they don’t put time in. But your values are like where you show up and put your time.

And so, that’s hard cause you don’t have that much of it. And I get increasingly busy where I think you often have this kind of trade off, do I come back to my one-on-ones and then I’m setting the value that I do not care about my team as much as I want to. Or do I go to this ERG group where if I don’t go, I’m setting this value that I don’t value this community. Neither of these are really acceptable trade- offs but you have to do it. And so, it’s hard, but this is why it matters so much – what actually works. So, I think I’ve evolved this a lot. Something I do every quarter is I just audit my calendar to understand where I’ve spent my time and I’m pretty ruthless about cutting back to get to where I want to be. I think that means like being less accessible than you want to. Sometimes, certain categories of outreaches. Doing this book, I found that I over committed to kind of just a number of things and I want to do them, but you just have to be like, what if I starve out by doing it. So blocking, reviewing every quarter, starting over, having meetings that expire automatically where after 16, they just go away and you have to remember to reschedule it. Having the courage to cancel stuff, having the courage to just stop showing up to something you don’t think is useful. Earlier in your career, I think you often believe that critical information and things happening behind these closed doors. But when you’re behind more and more of the closed doors, I think the illusion that this is where the important things happen kind of wears off.

CLAIRE: There’s less work FOMO, meeting FOMO over time.

WILL: Yeah. I think attendance as a form of recognition gets increasingly low on return over time.

CLAIRE: Yes. What I really appreciate about what you shared there is this idea that how you spend your time communicates your values. And in many ways, I think about myself like I have to check myself on that a lot. It’s like literally how I’m spending each hour of my day is seeing what I think is most important and where I think our priorities as a company should be. And that level of intentionality I don’t think is put at all oftentimes for us as leaders on where we’re putting our time. So, I just love this idea of literally how you are spending it, whether it’s doing outbound outreach for diversity inclusion efforts, whether that’s around interviewing, whether that’s preparing for those one-on-ones, whatever those blocks of times are going to, you’re essentially communicating to your team and this is what matters to me. And then I appreciate also just the quarterly reflection on that as well because it’s a way to sort of keep yourself accountable on that.

WILL: It’s not the case like how I spent my last quarter is like an obviously optimal thing that I should continue to reinvest in. So, I think just forcing reflections when you learn, right?

CLAIRE: Yes, absolutely. Will, literally, like I said, I have hundreds of questions, but I don’t want to keep you here all day on this podcast just talking to me. So, for the sake of time, one of the things that I was like, “I have to ask him about this when he comes on the podcast,” is I think the introduction to your book or sort of the preface, you talked about how a lot of people get into management for different reasons. Sometimes they think they could do a better job than their leader. Sometimes, they’re sort of excited for their career path. Sometimes, they’re just curious. And you said in the book that you didn’t say which one you were. So, I am curious to understand what drove you to become a leader. And then also in writing the book, just someone who, I do a ton of writing myself, people write books because they feel like they have something to say. For you, what was the driving force behind wanting to get this book out there as well?

WILL: The first one really at that point, Digg, the other managers had left and they were looking for kind of the person who didn’t realize that it was not the best management job to start managing at the scaling startup after the second round of layoffs. And I was like the easy con and I signed up for it and I was super excited. And so, it wasn’t super intentional, but the opportunity was there. And I’ve actually told this to a lot of people and this advice has never gone over well. It turns out this is not good advice to deliver. But if you find yourself at a bad company, there’s actually a lot of opportunity for you personally because there’s a lot happening and there’s a lot of room for you. But it turns out telling people they’re at a bad company doesn’t actually land very well. I’ve stopped trying to deliver this advice to people.

CLAIRE: Sure. Noted.

WILL: But I was at a bad company and I felt comfortable saying that at that point. In terms of writing the book, I think something that I have come to believe is that I think the piece that kind of comes to this the best is there’s this piece about working the policy, not the exceptions. And I found very few folks who are willing to tolerate the consequences of not making frequent exceptions. Exceptions are, for example, compensation. Like you really want to hire the candidate, you’re just going to give them a little bit more than you’ve given to people in comparable roles. You really don’t want to lose the star performer, so you’re going to make a new role just for them. That is a role a lot of people want, but you’re going to carve it out for them. I think it’s so easy to do that, but it basically means that you start penalizing the folks who I think are the core of great organizations who are quietly doing amazing humble work. They’re creating space for other people to be successful. They’re not grabbing all the opportunity for themselves. They’re like actually optimizing for the community, for the company, for the org. I just feel very strongly because I rightly or wrongly in part view myself as that person. How do we make sure these systems work for people who are not actively trying to gain the system? How do you make these systems work for people who are doing exactly what the system wants? How do we reward the people who are kind enough to actually operate the way we’ve asked them? And I think this book shows my set of processes that I found actually work for making sure that you can reward those sorts of people. And I found that along the way, these have lots of powerful benefits around creating opportunity that’s equally distributed to make it easy for folks who have not historically had easy access or who felt it was risky to kind of get access to some of these staff level projects or senior roles, to get access to them in a way where they don’t feel put at risk or put out. And so, I found that it’s actually possible to manage this way. There’s lots of uncomfortable parts about being very structured and process-driven and consistent. But I found that it’s much easier to have the awkward upfront versus this long trail of kind of rumor and innuendo about how things actually work. And so, I just really think if more companies and more leaders were willing to operate this way, there’s like a much more scalable model for them to take on. The orgs are much easier to be successful in. And I actually think they just work quite well. So, that’s sort of the dream that I have in putting this book out there.

CLAIRE: Absolutely. I love that. I mean, it’s the driving sort of undercurrent throughout. Each of the pieces that you have in it. And what it also honestly circles back to is your observation that it’s that modeling and it’s that consistency that is sort of the role of the individual of the leader, but it’s the processes and the systems overall that sort of make that transferable, that creates that to be sustainable over time and gets you the results that you want in the long term. I mean, your example of, “Oh, if we just gave this person like a little more just this one time.” It’s like, gosh, you can’t imagine how much that kills morale. What that says to the other team members who, like you said, have been quietly toiling. And when you, as leaders, when we’re more deliberate about thinking about what affects — again, our intentions, I think, at the time we’re thinking. Very short term. We just need this person, we just need this role. Just got to get this done. And we’re so easily blinded by that.

Actually, very last question here for truth. I can only imagine that there are some folks who are listening to this, they run companies or run teams much smaller than yours. And they’re thinking, “OK, in theory, this sounds nice. This sounds great for a company with over a thousand people and you running an org with a couple of hundred people. But what about my 50-person company and I’m running a 10%? Is it really optimizing so much for system and process? Are you really telling me I can’t make so many exceptions because I’m going to be viewed as inconsistent?” What do you have to say to those leaders?

WILL: Great process done well is you add as little as necessary and then you don’t throw it away. You like layer more pieces on. And so, I think this is a place where looking at like what your predecessor companies have done, and taking as little as you can and kind of slowly tweak these processes, I think works pretty well. I think, ultimately going back to exactly where we started, there’s something about figuring out what your values are as a company and your values as a leader, and then being honest about them where people can kind of select in to the company.

Saying that, there’s like a level of privilege in terms of being able to be in a spot where you’re hiring selectively enough that you can be like, “Well, we want people who actually have the same beliefs about what makes a good company as we do.” My first hiring management experiences were at Digg where we had just gone through layoffs. People were leaving, but we still need to hire. And we were like running out of money. And so, it was very difficult. We were not like, “Ah, this person is not as value aligned. They shouldn’t come in,” or something. We were like, “Yes, we will definitely talk to you.” We were different kind of mode there. I honestly do think it’s easier to be consistent. I actually think it’s just an easier way to manage and it’s an easier way to lead and that it has dividends. I personally really believe everyone should try to model this way. I think that said, I really think you have to figure out who you and your company’s values are and be honest to them. I think the worst thing is representing that you have a consistent structured way but then actually don’t operate that way. So, I think it’s more important to be authentic with your actual values than it is to manage the way I want you to manage.

CLAIRE: Yeah. And I also think consistency can even be to a level of revisiting processes or sort of stepping away from process. I think the thing that I think is actually widely applicable, regardless of organizational size or even companies stage is that anytime you think about something or manage in a more systemic way, you’re thinking about, what does this look like if it’s existing beyond me, and what is this looking like to get to where we want to be? And that’s what every team is looking to do ultimately. And so, your sort of method for it is, how do we have that be sort of a repeatable outcome? And that’s the beauty of having some level of process and system in it. So, wonderful.

WILL: As an ending thought, this ties into another belief of mine, which is that typically as you get further in your career, it’s not that you have things that you’re good at and things that you’re bad at or strengths and weaknesses. It’s more that you have like characteristics that surface in really positive and negative ways. And so, we talked a little bit about kind of rigidity as a leader and my leadership style and trying to get less rigid, but also like all of this process of this approach, this consistency, also comes from that rigidity. And so, they like manifest in different ways.

CLAIRE: Yes. There was another guest we had on this show, I don’t know if you know Cap Watkins, he used to be the VP of Design over at BuzzFeed. He talked about how it was, like you said, it was really characteristics in two sides of a coin of it being sort of his greatest superpower and then like the biggest pain in the ass for him too, and sort of the thing that he always struggled with the most. And so, yeah, I love that framing of our characteristics versus sort of strengths and weaknesses outright. Wonderful.

Well, thank you so much, Will, for your time. For all your insights. I highly recommend everyone to grab a copy of this lovely book. I appreciate you so much coming on the show.

WILL: Thank you so much. Really enjoyed it.

Written by Claire Lew

CEO of Canopy. My mission in life is to help people become happier at work. Say hi to me on Twitter at @clairejlew.