Will Larson
CTO, Imprint · 1 appearance on the record.
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Will Larson is a software leader who has headed engineering organizations at Digg, Stripe, Uber, Calm, Carta, and Imprint. He is known for his technology blog and books on engineering leadership, including An Elegant Puzzle and Staff Engineer.
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The record, in short
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Everything Will Larson said on In Depth that made the record, most notable first. Filter by type, assessment or year in the ledger →
Tech companies dodged engineering resource allocation for a decade through overhiring
“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…”
Believing engineering managers shouldn't get into technical details is an anti-pattern
“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 …”
Larson: Engineering executives must educate peers instead of shielding teams
“The most valuable thing as an executive you can do is educate like the other execs on how engineering works, not kind of protecting engineering from visibility from anyone else.”
CTOs and chief architects lack context for centralized technical decisions
“Chief architects and CTOs are pretty inefficient in terms of Actually getting enough context in their heads to make a good decision on any given, given point.”
Larson: Architecture review committees rarely make the best technical decisions
“And then committees, like in almost every architecture group turns into a committee where they have to balance their different perspectives, or they're just like slow and kind of inelegant. It's rarely true that a committee gets the best decision.”
Larson: Salespeople are uniquely talented individuals rather than fungible headcount
“Salespeople are not fungible, replaceable individuals. They're like uniquely talented people.”
Larson: Ideological purity against imperfect engineering metrics slows organizational learning
“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.”
Larson: Leaders should dive into details when teams violently disagree
“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.”
Will Larson: Large organizations inevitably depend on a few individuals' judgment
“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.”
Larson: Ask questions to extract insight from bad executive suggestions
“So like almost always when you get these like really like offhand random ideas from executives, there's a kernel of insight there that you can extract by kind of asking more, more detailed questions to them.”
Engineers cannot achieve true senior-level mastery in four years at one company
“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.”
Hiring managers should override interview panels when they have strong independent conviction
“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.”
New engineering leaders fail by assuming prior company context transfers directly
“The number one way that I see new engineering leaders struggle when they come to a company is they just assume the context from their previous company applies as is.
And if you've got new leaders who come in and really make a mess of things,
It's always becaus…”
Larson canceled Calm's monolith-to-services migration upon joining as CTO
“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.”
Companies document minor decisions but rarely record rationale for major strategic choices
“And one challenge at companies is like, you usually don't write down why they make the most important decisions.
Like you would
Sort of assume it's the opposite.
But if you go into a lot of companies, the small decisions are documented, but the really importan…”
Larson: Stubborn holdouts to new ideas often hold the most valuable context
“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.”
Larson: Strategy exists everywhere in companies but is rarely written down
“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.”
Larson: Writing strategy down improves it almost overnight regardless of quality
“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.”
Larson: Engineering strategy reduces to resource allocation and decision frameworks
“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…”
Carta appoints business unit navigators to act as local decentralized CTOs
“Something I've been trying at Carta and I increasingly believe in is something that at Carta we're calling navigators, but it's basically Having one person per area and roughly a business unit who is kind of the CTO from a technology perspective for that area …”
Larson: Unburdening top performers to boost output fails to scale
“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…”
Larson: Half of metrics' value is educating leadership mental models
“I think people want metrics to show reality. They want to show the truth, but half of metrics is showing the truth. The other half is educating people to inform their mental model about how the truth works.”
Larson: Engineering teams should generally have one manager per six-to-eight engineers
“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.”
Adapting to company context predicts if an executive lasts over a year
“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…”
Appearances (1)
| Episode | Date | Speaking time |
|---|---|---|
| A masterclass in engineering leadership from Carta, Stripe, and Uber | Will Larson (CTO at | Nov 16, 2023 | 1h 4m |