Will Larson

“A lot of the Least successful, but smartest people I've worked with were really strong systems thinking advocates.”

“The chief product officer Bruchali and I like spend a fair amount of time, like calibrating together and making sure, like, again, there's cases where there's like an exception, right? Cause there's like clear, clear issues happening for someone, but on averag…”

“Uber didn't have this as a written value, but implicitly Uber's, Uber's value was do what's good for your team and ignore everyone else because that will slow us down.”

“These are the three that I found really useful for any value. Like, is it honest? Is it applicable and can you reverse it? And if not, it's probably actually not helping the team make decisions.”

“I see a lot of people who are incredibly talented, but they try to hold their peers to a high standard, and then they're viewed as like combative or difficult to work with.”

“You know, when I was at Calm, Calm when I joined about 25 engineers, about a hundred when I left, And when I joined, we were going through a migration from our monolith to a number of services, and I canceled that migration.”

“Undocumented strategies at Stripe was we use a Ruby monolith. And so everything was done in the Ruby programming language with a few minor exceptions.”

“As an authority figure coming in, it's easy to kind of look at those folks as holdouts, people who are resistance, resistant to change, people who are, you know, just stubborn, but it's usually those folks who have like the most valuable context.”

“There's this like pervasive belief that there's no strategy anywhere, but I've really come to believe that strategies everywhere. It's just like rarely written.”

“If you just write things down, no matter how bad they are, your strategy will improve almost overnight. But if you don't write it down, it's incredibly challenging to improve your strategy.”

“Engineering strategy comes down to like largely like two kind of core ideas. There's like a resource allocation, like how are you investing the headcount and the, you know, that the budget that you have, and then how do you make how do you make decisions as th…”

“One challenge of the last decade, right, is that resource allocation was largely dodged by many companies because they just Decided to spend more and hire more folks. And so oftentimes the real constraint was, like, hiring velocity on a given team and your abi…”

“I think one of the lessons in management over the last decade has been that You know, managers are people leaders in that it is micromanagement that it is bad to get into the details. I think this is like an anti pattern because it creates disengaged and like …”

“So in a lot of these cases, the way to drive up productivity is to reduce the burden around like a small number of like really high performers. But if those performers ever leave, your productivity is going to drop massively as well. And so it's sort of a high…”

“So at Stripe, we had a reliability like SLA that we kind of extended to enterprise customers in terms of there was actually like a financial consequence to us if we dipped Below a certain level of uptime. Like I think it was less than four nines of API availab…”

“You can be ideologically like pure and say we shouldn't measure something, but all it does is slow down the learning of the organization around you. Doesn't actually help you accomplish your goal.”

“In cases where there is no clear path forward or where the folks who have the context around the path forward are like violently in disagreement, it pays to get into the details and make the decision yourself.”

“Something I believe pretty strongly is that teams should generally be one manager to like six to eight engineers. I think this is a really useful sizing mechanism.”

“And this is like one of the, to me, most predictive traits for whether an executive will last more than a year at a company. It's where they come in and they start with, Hey, can I, how can I change myself to fit versus how can I force my entire organization t…”

“Organizations are really, even, like, very kind of large organizations are the culmination of, like, a few individuals judgment, and there's just no way to escape that, even if you have, like, a huge budget trying to.”

“Typically when a CEO of a 500 person company feels their CTO is, is struggling, they're probably running into like one of two different things. Either the individual CTO is like causing friction with other people on the team. For some reason, like their peers,…”

“Anything else is going to get like a kind of consensus view, but like you don't need a consensus view on executive performance. You as a CEO need to have like a conviction view on like whether it's actually good or not.”

“I used to be a big believer in the umbrella concept where it's okay, we should protect our team from the reality and problems around them so that they can focus. But as you work with more senior teams but also even as you just work in generally, I've come to b…”

“I think that the best folks presenting to executives start super zoomed out and then zoom in to their specific problem over the course of like 30 seconds.”

“If you want, like, a high-quality exec meeting, you have to let the execs own the pace.”

“Talking things through live when people do have the shared like context, they just disagree is incredibly valuable and it's almost impossible to kind of like get to the end of these things on like a chat on Slack or something. You really do have to like talk i…”

“Like we kind of joked earlier, like this isn't an industry that teaches you how to do things. It's an industry that gives you opportunities to learn how to do things.”

“They can't develop everything you need to be an effective senior engineer in four years working in one company. You need to like see different views on these different problems to really kind of develop mastery.”

“Helping managers understand their job is to build conviction, not to kind of take the average of everyone else's conviction. And that they should override their team if they have conviction and they don't think that the concerns that are raised are meaningful.”

“And even in executive roles, I think there are people in there who are not getting traction after almost a year of searching, despite having many senior roles before.”