Will Larson's Blog, page 3

How to resource Engineering-driven projects at Calm? (2020)

One of the recurring challenges in any organization is how to split your attentionacross long-term and short-term problems. Your software might be struggling to scalewith ramping user load while also knowing that you have a series of meaningful security vulnerabilitiesthat need to be closed sooner than later. How do you balance across them?

These sorts of balance questions occur at every level of an organization.A particularly frequent format is the debate between Product and Engineeringabo...

Systems model of API deprecation

In How should Stripe deprecate APIs?, the diagnosisdepends on the claim that deprecating APIs is a significant cause of customer churn.While there is internal data that can be used to correlate deprecation with churn,it’s also valuable to build a model to help us decide if we believe thatcorrelation and causation are aligned in this case.

In this chapter, we’ll cover:

What we learn from modeling API deprecation’s impact on user retentionDeveloping a system model using the lethain/systems p...

Is this strategy any good?

We’ve read a lot of strategy at this point in the book.We can judge a strategy’s format, and its construction: both are useful things.However, format is a predictor of quality, not quality itself.The remaining question is, how should we assess whether a strategy is any good?

Uber’s service migration strategy unlockedthe entire organization to make rapid progress.It also led to a sprawling architecture problem down the line.Was it a great strategy or a terrible one? Folks can reasonably dis...

Steps to build an engineering strategy.

Often you’ll see a disorganized collection of ideas labeled as a “strategy.”Even when they’re dense with ideas, these can be hard to parse, and are a majorreason why most engineers will claim their company doesn’t have a clear strategyeven though my experience is that all companies follow some strategy, even if it’s undocumented.

This chapter lays out a repeatable, structured approach to drafting strategy.It introduces each step of that approach, which are then detailed further in their resp...

Operational mechanisms for strategy.

Even the best policies fail if they aren’t adopted by the teams they’re intended to serve.Can we persistently change our company’s behaviors with a one-time announcement?No, probably not.

I refer to the art of making policies work as “operations” or “strategy operations.”The good news is that effectively operating a policy is two-thirds avoidingcommon practices that simply don’t work.The other one-third takes some practice, but can be practiced in any engineering role:there’s no need to wa...

Career advice in 2025.

Yesterday, the tj-actions repository, a popular tool used with Github Actions was compromised (for more background read one of these two articles). Watching the infrastructure and security engineering teams at Carta respond, it highlighted to me just how much LLMs can’t meaningfully replace many essential roles of software professionals. However, I’m also reading Jennifer Palkha’s Recoding America, which makes an important point: decision-makers can remain irrational longer than you can remain s...

Setting policy for strategy.

This book’s introduction started by defining strategy as “making decisions.”Then we dug into exploration,diagnosis, andrefinement:three chapters where you could argue that we didn’t decide anything at all.Clarifying the problem to be solved is the prerequisite of effective decision making, but eventually decisions do have to be made.Here in this chapter on policy, and the following chapter on operations, we finally start to actually make some decisions.

In this chapter, we’ll dig into:

Ho...

Who gets to do strategy?

If you talk to enough aspiring leaders, you’ll become familiar withthe prevalent idea that they need to be promoted before they canwork on strategy. It’s a truism, but I’ve also found this ideaperfectly wrong: you can work on strategy from anywhere in an organization,it just requires different tactics to do so.

Both Staff Engineer and The Engineering Executive’s Primer have chapterson strategy. While the chapters’ contents are quite different, both presenta practical path to advancing your...

How to integrate Stripe's acquisition of Index? (2018)

While discussions around acquisitions often focus ontechnical diligence anddeciding whether to make the acquisition, the integration that followsafterwards can be even more complex.There are few irreversible trapdoor decisions in engineering,but decisions made early in an integration tend to be surprisingly durable.

This engineering strategy explores Stripe’s approach to integratingtheir 2018 acquisition of Index.While a business book would focus on the rationale for the acquisition itsel...

Diagnosis in engineering strategy.

Once you’ve written your strategy’s exploration,the next step is working on its diagnosis.Diagnosis is understanding the constraints and challenges your strategy needs to address.In particular, it’s about doing that understanding while slowing yourself down fromdeciding how to solve the problem at hand before you know the problem’s nuances and constraints.

If you ever find yourself wanting to skip the diagnosis phase–let’s get to the solution already!–thenmaybe it’s worth acknowledging that...