Will Larson's Blog, page 21

Notes on The Kool-Aid Factory's Planning Issue.

Recently I’ve been thinking a bunch about planning, and have been casting around for resources to work through while refining my approach. To my good fortune, my previous colleague, Brie Wolfson, has been working on a project delving into company process, The Kool-Aid Factory, and she has an excellent issue on planning.

These are my notes from The Kool-Aid Factory’s Planning issue.

(Note that I’m abbreviating The Kool-Aid Factory as TKAF from here on out.)

Planning’s purpose

TKAF defines the goa...

How to find engineering leadership roles.

I was recently chatting with a friend who asked about finding senior leadership roles, and particularly doing so while you’re already gainfully employed. The context of this discussion was managerial leadership roles within a software engineering organization, which for convenience I’m defining as leading groups of 20+ engineers (e.g. Director at Series C or later company) or being a functional leader of a smaller team (CTO, VPE).

Conducting a career search within these roles is odd for a few re...

How to safely think in systems.

The second most impactful book I’ve read is George Lakoff’s Don’t Think of an Elephant which lays out his theory of communication. Lakoff explores a fundamental organizational challenge: as you grow, it becomes increasingly difficult to communicate when you’re not in the room where a discussion happens. I once worked with a staff engineer who described their most significant contribution as giving initiatives catchy names and slogans to propel ideas further than any supporting data might.

That s...

Learning about personal finances.

Having a kid around has changed my perspective on many things, among them wanting to get more consistent in how our family approaches financial decisions. This is an area where I’ve spent a fair amount of time educating myself over the past decade, and I thought it might be useful for folks to see how my thinking has developed over my career, particularly given I started out knowing absolutely nothing on the topic.

For the first six years of my career, I accumulated money in a bank account. I di...

Notes on hiring a Foundation Eng leader.

I’ve recently had a few folks reach out for advice on hiring a Foundation Engineering leader based on my supporting that organization at Stripe. The first challenge with the question is defining what “Foundation Engineering” even means!

I joined Stripe to work with the “Sys” engineering group, which was short for “Systems,” and there were about thirty folks in Sys within the larger infrastructure organization that had… maybe sixty folks working across data, developer tools, financial infrastruct...

Closing calls: tell the best version of the truth.

Quite a few companies run you through their interview process, send you an offer nestled in a beautifully designed packet, and finish with a recruiter who’ll ask whether you accept the offer. This is the foundation of a hiring funnel, but it’s missing one valuable step: the closing call.

By the end of your hiring funnel, both you and the candidate have already invested a lot of time, and even slightly nudging them towards a “yes” will significantly improve your hiring efficiency. (Another prospe...

Create capacity rather than capture it.

Most growth companies are starved for experienced leadership. As they expand, continued growth builds up pressure on their existing leadership. This gets quite stressful! The rare executive manages to build an effective organization solely by investing in their existing team, but most supplement their organization with some external hires to maintain a balance of folks who’ve seen it before and folks who’re actively learning their role.

If you’re an executive challenged by your company’s growth,...

Getting to yes: solving engineering manager hiring loops that reject every candidate.

Hiring engineering managers is difficult, and many companies struggle with it. It’s a challenge to establish an effective interview loop. It’s tricky to convince candidates about your company’s opportunity. It can be hard to even get candidates to talk to you. Solving these issues takes time, but it’s fairly well understood work. What confuses many companies is that they solve all of these issues, and they still can’t hire engineering managers.

Companies struggling here often start to manufactur...

Pockets of rest enable careers.

Being burnt out at work feels like this year’s life crisis. Almost every conversation I have with a friend in the industry lingers on the topic of struggling to focus at work. Last week, I was chatting with a friend and we diagnosed their core career ambition as the deep desire to spend several years sleeping. Reflecting on the chaos of the last year, that does, indeed, sound like a solid career plan.

When asked for advice, I come back to two core bits.

First, try to avoid making career decision...

Can senior leaders make friends at work?

Chatting with a friend recently, they asked a question that I’ve spent time wondering about as well, “Can senior leaders have friends at work?” It’s reductive to pretend there’s one universal answer to this question, but most folks find it increasingly challenging to have friends at work as you get more senior. There are multiple factors at work, and it’s interesting to dig into it a bit.

The biggest reason is that your peers have already developed a full life outside of work. Earlier in their c...