Lessons from the engineering management trenches - real experiments, honest outcomes
7 posts
I Thought It Was Me: Why I quit being an EM the first time (and what changed when I tried again 10 years later). I had training, support, resources - and I was still miserable. I couldn't name what was wrong, so I assumed I wasn't cut out for it. Turns out, I just couldn't identify what I was actually struggling with. This is about the trap most new EMs fall into, and why naming the problem changes everything.
I Love My Job and It's Exhausting: The weight nobody warns you about when you become an engineering manager. You don't just carry your own load anymore—you carry your team's issues, your peers' struggles, and eight projects in your head at once. Your brain never stops. The emotional toll is real. And you can't turn it off even if you wanted to. This is the part they don't tell you about becoming an EM. Both things are true: the work is worth it, and it's exhausting.
What If Your Chaos Is Actually Your Superpower? The realization that changed how I see my leadership style (and why trying to be calm was making me worse). I send messages then solve them myself. I prototype instead of spec'ing. I jump on problems before thinking them through. Everyone else seems so measured and I felt like I was failing. Then a friend asked: "Isn't that just a superpower?" This is about finding your own management style instead of trying to be someone you're not.
Over-Communication Doesn't Exist: The phrase that changed how I manage (and why asking twice costs nothing). Nobody ever said a project failed because we asked the same question twice. But I've seen dozens fail because we didn't ask at all. This is about why clarity is free, assumptions are expensive, and the real barrier you're building when you over-communicate.
The Invisible Work Problem: Why engineering managers only get noticed when something breaks (and why that's actually the job). Your team crushes it, and it looks like they're just naturally great. Your team struggles, and everyone wonders what you do all day. This is about the invisible work that makes teams perform, the imposter syndrome that comes with it, and why there's no test suite for management.RetryClaude does not have the ability to run the code it generates yet.
The Restaurant Lie: The bizarre reason you can't give honest feedback (and why your team is suffering). The 'Food Was Great' lie doesn't just happen to waitresses. It's happening in every code review. This is about the social friction that makes us choose comfort over continuous improvement, and the simple framework I use to break the cycle.
I spent six months trying to make it work. Six months of coaching conversations, adjusted expectations, and "one more chance" discussions. Six months of convincing myself that if I just found the right approach, the right project, the right motivation - it would click.