Jan 7, 2024 · 1h 16m · lennys-podcast
The engineering mindset | Will Larson (Carta, Stripe, Uber, Calm, Digg)
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In this conversation, engineering executive and author Will Larson breaks down pragmatic frameworks for systems thinking, engineering strategy, developer productivity, cross-functional alignment, and sustainable writing habits in a post-ZERP tech landscape.
How this conversation actually went
Every chapter scored 0–10 on four independent dynamics. Hover any point for the reasoning behind the score. Lenny holds 21.9% of the talking time here. How this is scored →
Lenny as informed peer 3.9 Guest teaching 4.8 Guest disagreement 1.6 Lenny pushing back 1.3
speaking balance: gold is Lenny, purple is the guest (3 minute bins)
Sharpest disagreement ▶ 16:52 Challenging the assumption of written strategy
Will directly dismisses the conventional assumption that product or business teams possess formal strategies, stating that almost no company actually has a written strategy.
Hardest push from Lenny ▶ 7:18 Lenny probes the premise of not upsetting engineersLenny presses Will on whether leaders genuinely no longer need to worry about angering engineers versus whether coddling was simply poor management.
Biggest teaching moment ▶ 11:41 Explaining stocks and flows in systems thinkingWill breaks down systems thinking from first principles using ecological models and Donella Meadows' framework, giving Lenny an intuitive lens he had not encountered before.
Lenny holds their own ▶ 1:01:44 Lenny details Airbnb's value pruningLenny demonstrates deep organizational expertise by explaining how Airbnb removed aspirational values like 'simplify' when leaders realized they were dishonest descriptions of company behavior.
the scores for every segment, with the reasoning behind each
| Chapter | Topic | Lenny as informed peer | Guest teaching | Guest disagreement | Lenny pushing back | Why |
|---|---|---|---|---|---|---|
| The Post-ZERP Shift in Engineering Leadership | 4 | 5 | 2 | 2 | Lenny opens with an informed question regarding the macroeconomic shift from the ZERP era to modern engineering realities. Will shares deep operational insights about how engineering managers previously spent excessive time hiring and coddling engineers, reframing the current downturn as a healthy return to accountability. | |
| Demystifying Systems Thinking in Software Engineering | 3 | 7 | 2 | 1 | Lenny invites Will to demystify systems thinking, acknowledging he has never heard the concept explained cleanly through stocks and flows. Will provides a masterclass on systems modeling, illustrating failure modes at Stripe and practical applications in hiring funnels. | |
| Crafting Pragmatic and 'Boring' Engineering Strategies | 4 | 6 | 3 | 2 | Will gently pushes back on the premise that product or business teams usually have clear strategies, arguing that most companies operate with unwritten or poor strategies. Lenny synthesizes Will's case studies at Uber and Stripe by noting the overarching role of deliberate constraints in strategy. | |
| Strategy Frameworks and Recommended Reading | 3 | 4 | 1 | 1 | Lenny asks for key resources and literature on engineering strategy. Will provides a tailored reading list and previews the strategy frameworks he addresses in his upcoming book. | |
| Sponsor Message: Vanta | 6 | 3 | 1 | 1 | Following an ad read, Lenny and Will engage in a peer-to-peer discussion on writing and content creation. Lenny actively contributes his own philosophy on avoiding burnout, finding a niche, and treating writing as a long-term infinite game. | |
| Aligning Product Managers and Engineering Managers | 5 | 6 | 2 | 2 | Lenny asks how PMs and EMs can resolve friction, and Will details Carta's practice of giving PM-EM pairs identical performance review ratings. Lenny probes how ladder definitions and incentives interact, and notes how design managers fit into this triad. | |
| Measuring Engineering Productivity and Developer Velocity | 4 | 6 | 2 | 1 | Lenny asks about concrete metrics and dashboards for engineering velocity, citing Nicole Forsgren's previous appearance on the podcast. Will explains the diagnostic utility of DORA metrics while warning against treating them as definitive scorecards for executive boards. | |
| Defining Authentic and Actionable Company Values | 6 | 4 | 1 | 1 | Will breaks down the criteria for great corporate values (honest, applicable, reversible). Lenny strongly validates and extends the framework by sharing Airbnb's experience cutting non-descriptive values like 'simplify' that didn't reflect reality. | |
| Failure Corner: The Digg v4 Rewrite Disaster | 2 | 5 | 1 | 1 | Lenny invites Will to share the Digg v4 rewrite disaster for the Failure Corner segment. Will recounts the multi-week outage, emergency caching rewrites, Python default parameter bug, and the formative management lessons learned from leading a collapsing team. | |
| Promoting The Engineering Executive's Primer | 2 | 2 | 1 | 1 | Lenny closes the interview with the lightning round and promotion for Will's book, The Engineering Executive's Primer. Will answers rapidly regarding interview questions, life mottos, and favorite essays. |
Statements from this episode (18)
Larson: Engineering managers shifted from 50%+ hiring time to almost zero interviews
“Like a lot of engineering managers are spending half their time or more hiring like 18 months ago, and now they're doing like two interviews a month or less, maybe zero interviews a month.”
Larson: Companies harm engineers by coddling them and sheltering them from reality
“Like one of my like hobby horses is that I think that we often treat engineers a little bit like children instead of giving them like the responsibilities and ability to actually thrive as adults.
And so like, oh, the engineers won't want to do that work.
We…”
Larson: Many smart but unsuccessful people over-rely on systems thinking
“A lot of the Least successful, but smartest people I've worked with were really strong systems thinking advocates.”
Larson: Common hiring bottleneck is managers lacking confidence to extend offers
“And so for a lot of candidates or a lot of pipelines, the biggest issue is hiring managers don't want to extend any offers because the hiring managers can't get to confidence on any candidate.”
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”
Larson: Stripe strictly enforced a Ruby monolith strategy
“Another good example at Stripe was this idea of We run a Ruby monolith, and that's like, that's what we did.”
Larson: Bad strategies stem from willful disbelief of accurate diagnoses
“Almost all bad strategies basically come down from a willful disbelief of what an accurate diagnosis is, which means then your guiding policies are kind of incoherent to begin with.”
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: Write a few great essays rather than starting a newsletter
“I tell people if you just want to like write something that is going to help advance your career, you should really focus on writing like two or three really good things and spend a ton of time drafting, revising, getting feedback. You just focus on making lik…”
Larson: Carta gives EM and PM pairs the same performance rating
“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…”
Larson: VC Spending Benchmarks Placate Boards but Do Not Improve Engineering
“You know, this idea that if you just have the right benchmarks, like DCs won't judge you for spending too much in engineering, but it doesn't actually help you get to the right place. It just helps you get your board to be less angry at you.”
Larson: Reporting Sprint Points to Boards Is Completely Fake
“A lot of engineers report on like sprint points or stuff like that to their board, which are just like totally, totally fake thing to be like reporting on.”
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: Uber prioritized local team speed over cross-team coordination
“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.”
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.”
Rachitsky: Airbnb cut 'simplify' from values for not reflecting reality
“So at Airbnb, we had six values initially. One of them was simplify. And a year or two later, everyone just realized we're not actually good at this. We want to simplify, but we're not great at the skill and value should describe who you are, not who you want …”