Will Larson's Blog, page 15

Mailbag: What should you do if you report to an underperforming executive?

Recently, an email came in asking what to do when you report into a mediocre or underperforming executive.I’ve gotten variants of this question a number of times over the years, and it’s worth digging into a bit:

Have you written anything about working in middle management where you are managing a high performing team but under a low performing executives?How do you demonstrate your value to the broader organization so that your team remains motivated,and you can eventually move across group...

Trying Plausible.

I’ve been wanting to spend some time trying out recentdeveloper and infrastructure tooling, starting with taking Tailscale for a spin(it’s quite nice).Next, I’ve been thinking about replacing Google Analytics on this blog for some time,and decided to try out Plausible.io as a replacement.

For the record, I don’t have any profound gripes with Google Analytics, rather I’d say thatI’m profoundly grateful to GA. It’s a tool that I’ve greatly benefitted from over the past decade,and it hasn’t c...

Getting a job as an engineering executive.

I started my first executive job search when I was 25.Eventually, I got an offer to lead engineering at a startup with four engineers,which I turned down to join Uber.It wasn’t until a decade later that I joined Calm and started my first executive role.If you start researching executive career paths, you’ll findfolks who nominally become engineering executives at 21 when they found a company,and other that are 30+ years into their career without taking an engineering executive role.

As the...

Make an effective executive LinkedIn profile.

tl;dr - it’s valuable to update your LinkedIn profile to be a concise, accurate, and current summary of your accomplishment. Spend at most two hours updating it, then ask a friend (ideally a recruiter) for feedback. Incorporate that feedback and don’t think about your profile again for at least a year.

While writing my notes on landing an engineering executive role, a topic that came up in feedback a number of times was how valuable it is to have a reasonably good LinkedIn profile. There’s abso...

How to capitalize engineering costs.

There are many important meetings in your first ninety days as a new engineering leader, but one that’s both easy to forget and surprisingly important is your first meeting with the finance team. There’s a lot to learn from the finance team, particularly drilling into your profit and loss statement, but there’s one narrow topic that causes a surprising amount of frustration between engineering and finance teams: how do you capitalize software engineering costs?

Capitalizing software costs is a f...

Trying Tailscale.

Like most folks working in infrastructure engineering in 2014, I really enjoyed Google’s BeyondCorp whitepaper. My foremost personal interest was grounded in the fact that Uber’s contemporaneous security implementation didn’t include a VPN, so it was interesting to see a well-thought description of fostering security without over-reliance on a hardened network for employee devices. I had a second, longer-term, personal interest as well, which was never again having to argue with a coworker about...

Measuring an engineering organization.

For the past several years, I’ve run a learning circle with engineering executives. The most frequent topic that comes up is career management–what should I do next? The second most frequent topic is measuring engineering teams and organizations–my CEO has asked me to report monthly engineering metrics, what should I actually include in the report?

Any discussion about measuring engineering organizations quickly unearths strong opinions. Anything but sprint points! Just use SPACE! Track incident...

A brief rant on converging compliance regimes.

Although I’ve never worked exclusively on compliance, much of my work over the past decade has touched on reconciling between product and compliance goals, and over that time I’ve developed something of a pet theory on the evolution of compliance over the next five to ten years: I expect customer-oriented compliance to converge on a unified set of controls.

While today there’s a wide distance between GDPR, CCPA, HITRUST, FedRAMP and SOC2, I generally expect the gaps between these various framewo...

Lessons not worth learning.

A few weeks ago I had a call with a startup founder who was frustrated with their team. The team kept getting distracted by interesting work, and was avoiding the most important work to move the business forward. Was it possible to build a team that simply does the important work without getting distracted by more interesting or energizing work? Why can’t you build a team that operates rationally to the businesses interests rather than their own?

My advice was that there are basically two paths ...

2022 in review.

Previously: 2021, 2020, 2019, 2018, 2017

After the past two years, it’s odd to write an annual reflection where my first thoughts are happy rather than bleak.The truth is that there is a lot of bleak out there right now–just look at the layoffs and the funding environment–but whilelast year was an unusual and challenging one for me, this one was relatively quiet for me and my family.

That said, even a quiet year is worth a bit of introspection, so here is my annual note.

(If you’re writing a y...