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Chaotic-Good Engineering Management

Thoughts and stories about running engineering teams in the chaotic high-growth phase.

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That Free Puppy Sure Is Cute

Why writing software has never been the expensive part. There are a couple aphorisms about software development that seem apt right now. 🥛 Code doesn't age like wine, it ages like milk. 🐶 Open source software isn't just "free as in beer", or "

"Tokenmaxxing" Is Not Productivity

We All Want to Be Productive Everyone wants to be productive. As a manager, we don’t produce much ourselves, so our productivity is the vicarious productivity of our whole team. It’s an important part of how we measure ourselves and how we are measured. If there&

Leading Without a Map

How to Stay Steady When the Job Itself is Changing No one can deny that our industry is in a period of great change. This industry never stops, and the rate goes up and down but change is a constant. Like it or not " change calls the tune we

Let Your Teams Own Their Processes

Design APIs, Not Implementations When it comes to team operating principles, I'm sure we've all encountered the leader who values uniformity seemingly for the sake of it. Every team has the same ceremonies, on the same days. Status reports are via a templated slide deck with

How to Be Better at Talking About 'Tech Debt'

Tech Debt started out as a useful metaphor. You 'borrow' from the future to achieve an outcome today. Much in the same way you can achieve home ownership earlier by taking out a mortgage after saving enough for a down payment. However, the way it's used

The Trust Triangle

Why low levels of trust leads to low levels of performance. A theme I find myself coming back to over and over again is the three-way relationship between Autonomy , Accountability , and Alignment and how those interact to produce high-performing teams. In case I need to define the terms:

Gatekeepers vs. Matchmakers

How your interviewing posture reflects your leadership culture I estimate I’ve conducted well over 1,000 job interviews for developers and managers in my career. This has caused me to form opinions about what makes a good interview. I’ve spent the majority of it in fast-

A Fire is Not an Emergency for the Fire Department

Good leadership is remaining calm and steady while everything crashes around you. Yesterday (Oct 20, 2025), AWS had a major incident . A lot of companies had a really bad day. I’ve been chatting with friends at impacted companies and a few had similar stories. Their teams were calm

Co-Pilots, Not Competitors: PM/EM Alignment Done Right

In commercial aviation, most people know there's a "Pilot" and a "Co-Pilot" up front (also known as the "Captain" and "First Officer"). The ranks of Captain and First Officer denote seniority but both pilots, in practice, take turns filling

Am I solving the problem or just coping with it?

One of the most valuable questions I ask myself. Solving problems and putting in processes that eliminate them is a core part of the job of a manager. Knowing ahead of time whether or not your solution is going to work can be tricky, and time pressures and the urgency

How to Be a Leader When the Vibes Are Off

...and the vibes are definitely off It feels different in tech right now. We’re coming off a long era where optimism carried the industry. Something has curdled. AI hype, return-to-office mandates, and continued layoffs have shifted the mood. Managers are quicker to fire, existential dread has

Stop Hunting for Heroes and Villains: Start Thinking in Systems

I was listening to a podcast the other day (I'm not going to link to the specific episode because it's about current events and there are plenty of places to discuss those. I don't want this to become another one but I'll

Scapegoating Only Worked in Ancient Times

💡 This is a guest post by Lin Byrne, a Principal Infrastructure Engineer who previously held engineering management roles at companies like Okta and CircleCI. Scapegoating comes from an ancient ritual where a community would place its sins onto a goat and send it away. The act served as a

‘Labs’ teams, Skunkworks, and Special Projects: Beware

In a previous post , I talked about balancing ‘creating work’ and ‘destroying work’ such that the backlog does not become a huge mental burden on everyone to the point that it gives the impression that “the dev team is slow” or “we’

Your Backlog is not a Hoarder House

A theme I return to a lot in my head is the difference in friction between "creating" and "destroying" work to be done. It's much much easier to dream up another thing to build, a new feature, heck even a new product than it