Will Larson
CTO, Imprint. On 2 shows, 2 appearances. The Shows tab opens the full record on each.
executiveauthorengineerinvestor@Lethain ↗LinkedIn ↗lethain.com ↗
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.
2shows
2appearances
53statements
3resolved
2supported
0contradicted
67%fully supported
1said about them ↓ Everything Will Larson said on any show that made the record, most notable first. Each card names its show and opens the statement there.
Larson: The biggest risk to creators is burnout, not slow initial growth
“The biggest risk to content creation of any sort is quitting soon because you get burned out. The biggest risk is not that you grow too slow initially.”
Larson: Metrics Exist to Educate Executives, Not Be Perfect Datasets
“Metrics are about educating the people consuming the metrics about the reality of the rich data underneath. They're not about this perfect data set that shows everything. Starting with something mediocre, and the Dora metrics are really helpful for diagnosis, …”
Larson: Useful company values must be honest, applicable, and reversible
“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.”
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…”
Larson: CTO struggles usually stem from peer friction or poor shipping velocity
“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,…”
Larson: CEOs need a conviction view, not consensus, on executive performance
“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.”
Larson stopped shielding engineering teams and now exposes them to messy reality
“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…”
Start executive presentations with conclusions and stop talking if they agree
“But when you present to execs, you should start with the conclusion. And then, if they already agree with you, stop presenting. Like, there's no reason to keep presenting.”
Larson: High-quality executive meetings require letting executives set the pace
“If you want, like, a high-quality exec meeting, you have to let the execs own the pace.”
Larson: Important disagreements with shared context must be debated live, not asynchronously
“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…”
Tech executives are struggling to find jobs after a year of searching
“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.”
Larson: Uber operated under a strict no-cloud policy in 2014
“At Uber, we only used our own data centers. We didn't use the cloud, and this has changed since, since the era I was there, but in the, like, 2014 era, no cloud, and we had a strict no cloud policy”
The other half of the tape: Will Larson's own voice is left out of every number here. Other people bring the name up 1 time in 1 episode across the shows. every mention, with the transcript →
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One line per show, most statements first. The link opens Will's full record on that show: the calibration, argument clarity, speaking style and every statement made there.
| Show | Role there | Eps | Statements | Record | |
|---|---|---|---|---|---|
 IN DEPTHLEDGER | CTO, Imprint | 1 | 36 | 100% 1/1 | full record on In Depth → |
| LENNY'S PODCASTLEDGER | CTO, Imprint | 1 | 17 | 50% 1/2 | full record on Lenny's Podcast → |