A few years into my time as a people leader, I started noticing a gap between what I thought I was doing for people and what I was actually doing. I was mentoring — regularly, I thought, genuinely. Giving feedback on their work, talking through career paths, offering perspective when they were navigating difficult situations. I felt like I was investing in people. And I was. But I was doing it in a way that stayed largely inside the room. ...
There’s a conversation I’ve had more times than I can count, and it usually starts the same way. An engineering leader — smart, experienced, under pressure — says something like: “We need to move faster. What can we do right now?” And the honest answer, the one that actually matters, is almost always: “It depends on what you built three years ago.” Business agility is mostly an architectural property. Not entirely — teams, culture, and incentives all matter — but the ceiling on how fast you can move is often set by decisions that happened before the current pressure existed. This is uncomfortable to say because it implies that the answer to “why are we slow now?” is partially “because of choices we made when things were fine.” But it’s true, and pretending otherwise doesn’t help anyone. ...
The hardest part of a performance conversation isn’t the conversation. It’s the six weeks before it, when you know you need to have it and keep finding reasons not to. Someone in your reporting chain is not performing — not dramatically, not in a way that’s creating a crisis yet, but in a way that you can see and that people around them are starting to notice. Their direct reports, their peer managers, the cross-functional partners they work with. Every week you don’t address it is a week the broader team watches you not address it, which is its own signal about what gets tolerated. ...
“Move fast and break things” is a mantra built for a specific context: small team, early product, learning fast — figuring out whether you’re building the right thing at all — matters more than stability, the cost of a broken thing is recoverable. In that context, it makes real sense. Speed is the only asset a small team has that a large organization doesn’t. Breaking things, learning, and fixing quickly is genuinely the right tradeoff when the alternative is being slow and careful about something that might not matter at all in six months. ...
Every engineering team has a brand. Most of them haven’t built it deliberately — it formed on its own, through the experience of people who worked there, the things those people said when they left, the code quality visible in open-source projects or interview processes, and the stories that circulated inside the company about how the team operates. You don’t always choose it; you inherit it, or build it by accident. ...
There’s a leadership skill nobody teaches you directly: what to do when you genuinely disagree with your manager’s call and the call still has to be made. I’ve been on both sides of this enough times that I have a fairly worked-out view of how to handle it. But I also remember the period before I had a worked-out view — before then, I defaulted to one of two bad instincts depending on the situation: either folding too early to avoid friction, or staying dug in past the point where it was useful. Neither serves the work. ...
At some point, most engineering leaders will sit across from a finance partner who needs a 15 or 20 percent reduction in cloud spend by end of quarter. It’s one of those conversations that’s uncomfortable not because the math is hard but because the decisions behind the math are real — you’re choosing what to protect and what to let get slower, noisier, or more constrained. Having been through this more than once, I’ve developed some views on which cuts are straightforward and which ones look cheap in the short term but cost you later. ...
About two years ago, someone left one of the engineering teams in my org whose contribution I didn’t have full visibility into until after they were gone. Not dramatically underappreciated — they were well-compensated, well-reviewed, treated respectfully. But I hadn’t fully seen what they were doing, and when they left, the teams they’d been quietly supporting revealed the size of the gap in the way that only becomes fully legible in retrospect. ...
I started this blog without a plan — that’s the honest answer. There was no content strategy and no brand I was consciously building. Just things I was thinking about — leadership decisions I’d made and wasn’t sure I’d made correctly, patterns I kept seeing across teams, ideas I’d formed but never tried to articulate out loud — and at some point someone suggested I write them down and put them somewhere. So I did. ...
If you’re doing the job well, your team will vent to you. They’ll tell you about the project that’s frustrating them, the colleague who’s driving them up the wall, the process that feels pointless, the decision that came down from leadership and doesn’t make any sense. They’ll bring you anxiety about their career trajectory, frustration about not getting a promotion, worry about whether the team’s work is valued. And they should be able to do this — because a manager who can’t receive this is a manager their team will learn not to trust. ...