Will Larson's Blog, page 9

Leadership requires taking some risk.

At a recent offsite with Carta’s Navigators, we landed on an interesting topic: leadership roles sometimes mean that making progress on a professional initiative requires taking some personal risk.

This lesson was hammered into me a decade ago during my time at Uber, where I kicked off the Uber SRE group and architectured Uber’s self-service service provisioning strategy that defined Uber’s approach to software development (which spawned a thousand thought pieces, not all complimentary). I did b...

Friction isn't velocity.

When you’re driving a car down a road, you might get a bit stuffy and decideto roll your windows down. The air will flow in, the wind will get louder,and the sensation of moving will intensify. Your engine will start working a bitharder–and louder–to maintain the same speed.Every sensation will tell you that you’re moving faster, but lowering the windowhas increased your car’s air resistance, and you’re actually going slower.Or at minimum you’re using more fuel to maintain the same speed.

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More (self-)publishing thoughts.

I recently got an email asking about self-publishing books,and wanted to summarize my thinking there.Recapping my relevant experience, I’ve written three books:

An Elegant Puzzle was published in 2019 as a manuscript by Stripe Press (e.g. I wrote it and then it was released as is),which has sold about 100,000 copies (96k through the end of 2023, and selling about 4k copies a quarter over past two years), Staff Engineer which I self-published in 2021, which has sold about 70,000 copies (also ...

Digital release of Engineering Executive's Primer.

Quick update on The Engineering Executive’s Primer. The book went to print yesterday,and physical copies will be available in March.Also, as of this moment, you can purchase the digital edition on Amazon,and read the full digital release on O’Reilly.(You can preorder physical copies on Amazon as well.)

Thesis on value accumulation in AI.

Recently, I’ve thinking about where I want to focus my angel investing in 2024,and decided to document my thinking about value accumulation in artificial intelligencebecause it explains the shape of my interest–or lack thereof–in investing in artificialintelligence tooling. I’ll describe my understanding of the current state, how I think it’llevolve over the next 1-3 years, and then end with how that shapes what I’m investing in.

My view on the the state of play today:

There are three funda...

High-Context Triad.

The past couple weeks I’ve been working on three semi-related articles that I think of as the “High Context Triad.” Those are Layers of context, Navigating ambiguity, and Tradeoffs are multi-dimensional. One of my background projects, probably happening in 2025 or 2026 after I’ve finished my nascent project on engineering strategy, is publishing a second edition of Staff Engineer, and I intended these three articles as supplements.

I’ve really enjoyed writing these pieces, because the first on c...

Useful tradeoffs are multi-dimensional.

In some pockets of the industry, an axiom of software development is that deploying software quickly is at odds with thoroughly testing that software. One reason that teams believe this is because a fully automated deployment process implies that there’s no opportunity for manual quality assurance. In other pockets of the industry, the axiom is quite different: you can get both fast deployment and manual quality assurance by using feature flags to decouple deployment (shipping the code) and rele...

Navigating ambiguity.

Perceiving the layers of context in problems will unlock another stage of career progression as a Staff-plus engineer, but there’s at least one essential skill to develop afterwards: navigating ambiguity. In my experience, navigating deeply ambiguous problems is the rarest skill in engineers, and doing it well is a rarity. It’s sufficiently rare that many executives can’t do it well either, although I do believe that all long-term successful executives find at least one toolkit for these kinds o...

Layers of context.

Recently I was chatting with a Staff-plus engineer who was struggling to influence his peers. Each time he suggested an approach, his team agreed with him, but his peers in the organization disagreed and pushed back. He wanted advice on why his peers kept undermining his approach.After our chat, I followed up by talking with his peers about some recent disagreements, and they kept highlighting missing context from the engineer’s proposals.As I spoke with more peers, the engineer’s problem beca...

Those five spare hours each week.

One of the recurring debates about senior engineering leadership roles is whether Chief Technology Officers should actively write code. There are a lot of strongly held positions, from “Real CTOs code.” at one end of the spectrum, to “Low ego managers know they contribute more by focusing on leadership work rather than coding.” There are, of course, adherents at every point between those two extremes. It’s hard to take these arguments too seriously, because these values correlate so strongly wit...