Engineering Management

I’ve interviewed a lot of senior engineering and engineering leadership candidates over the years, and the pattern I’ve noticed in how those conversations go is fairly consistent. The first thirty minutes are almost always fluent — people come prepared, they have good stories about scale and complexity and the hard technical decisions they navigated. They’ve thought about leadership principles, they can talk about team development and conflict and cross-functional alignment. They’ve done the preparation, and the preparation shows. ...

I want to write an honest version of this, not the version that reads like an annual letter to shareholders. So let me tell you what I actually learned over the past couple of years — the things I changed my mind about, the things that were harder than I expected, and one or two that were genuinely easier. The first thing I got wrong, and kept getting wrong for longer than I should have: I underestimated how much context my direct reports actually need, and I overestimated how well it travels. When you’re leading other leaders — when your direct reports are engineering managers, not engineers — information passes through at least two layers before it reaches the people doing the work. I knew this in the abstract, but what I hadn’t appreciated is how much signal drops at each layer — not through negligence or incompetence, but because each person in that chain is doing the normal human thing of filtering for relevance and adding their own interpretive frame. By the time the context I thought I’d communicated reaches a senior engineer making a technical decision, it might have lost exactly the nuance that would have changed the decision. ...

A few years ago, I gave a performance review that I thought was honest and balanced. I covered the person’s genuine strengths, which were real and worth celebrating. I mentioned the areas for growth, but I kept the language careful — “continues to develop” rather than “struggles with,” a sentence about the opportunity to build more cross-functional relationships rather than a direct observation that the person was creating friction with peer teams. The review was true, technically. But it was soft in the places that mattered, and I knew it while I was writing it. ...

When you’re running a large engineering organization — multiple teams, multiple managers reporting to you — every metric you put on a weekly review becomes a directive. Not because you framed it that way, but because your managers are smart people who understand what you’re paying attention to. The moment something lands on your leadership dashboard, three or four teams start orienting around it simultaneously. I learned this slowly, and then all at once. ...