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. Have you been enjoying these Heartbeat episodes, lately? If so, it’d mean the world to me if you wrote us a review in iTunes. The more reviews we have, the more we’re able to share all our lessons from leaders. Thank you! 3 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 C