Professional

Recently I caught up with a colleague who was one of the best developers I’ve ever worked with. They were also the hardest person to promote. The CTO’s pushback to my request came in one sentence: “They were never in the war room.” The CTO wasn’t wrong about the facts. They were never in the war room, because their systems never warranted one. Everything they shipped was resilient against the failure modes we had, documented well enough that other teams and users could answer their own questions, and boring in the way that well executed systems are boring. On top of that, culturally, they made the people around them better, quietly, without ever boasting about it. ...

I’ve watched talented engineering teams burn out not from working too hard, but from working without direction. The pattern is always the same: leadership announces a new strategic pivot every quarter, teams scramble to adjust, morale craters, and your best people start updating their LinkedIn profiles. The problem isn’t the changes themselves. It’s that without a guiding vision, every shift feels like a complete reversal rather than a necessary course correction. ...

Why Your Strategic Planning Fails (And How to Fix It) I’ve seen more agile planning sessions derailed by politics than by any technical challenge. It always starts the same way. You get the right people in a room—Product, Engineering, Sales, Finance—and for a moment, it feels like a powerful alliance focused on building the future. A spy’s guide to strategy helped me realize these sessions unfold in three acts: Alliance, Competition, and Endgame. ...

I got into management because I saw myself as a player-coach. I could create software and make my teams more effective. The most rewarding part? Shielding creative people from bad direction and then watching them delivering results. Success gave me more influence to shape process and continue to help my teams be their best. Chris Dixon’s recent, high-profile shift from “Management” back to “Engineer” made me pause. He’s a true champion of the possible who had an outsized impact on my early career, and his move forced me to think about my own direction. ...

I was reviewing an older repository during a production incident the other day and couldn’t figure out what sections of the code were doing or what the overall system looked like. It’s so frustrating to be in undocumented code. Software documentation is a mature pillar of engineering these days. The tools are there, the patterns exist, the documentation standards are well-established. We just… don’t do it. Why don’t we when there is documented correlation between high performing engineering teams and open and accessible codebases? ...