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.
The practical change I made: I communicate more directly with the broader organization than I used to, in ways that don’t bypass my managers but supplement them. Not with directives that skip levels — that’s destructive to the trust you need to build with your direct reports — but with context, reasoning, and framing that the whole organization can access directly. The goal is that when someone four levels down makes a judgment call in a gray area, they have enough of my thinking in their heads that they can reason about it the way I would.
The second thing: I thought I understood how long things take at this scale, and I didn’t. Not just in the sense of individual projects running long — I expected that. The institutional things — changing a process, shifting a team’s technical direction, moving from one operating model to another — move slower by an order of magnitude than I anticipated, and the gap between when you make the decision and when you see the behavior change is long enough that you’ll sometimes be tempted to make the decision again. I’ve had to develop patience with organizational lag in a way I didn’t need to when I was working at smaller scale.
The third thing, and this one I mostly discovered by being wrong: I used to believe that the best thing I could do for a struggling team was get closer — more involved, more present, more visible. Sometimes that’s right. But I’ve learned that there are situations where a struggling team’s problems are primarily upstream — resource constraints, priority conflicts, unclear charters — and adding my presence to the team creates the impression of action while the real problem remains unresolved. The harder and more useful intervention is often doing the organizational work above the team rather than the operational work within it. Getting my hands dirty can feel more satisfying, and it can be the wrong move.
What was harder than I expected: maintaining real relationships with the people in the organization when the organizational distance grows. Not the quarterly all-hands where I’m visible. Actually knowing the engineers, understanding what they’re working on, having enough genuine familiarity that feedback goes both ways and I’m not just operating on sanitized reports. That gets harder as the organization grows, and it requires active effort that’s easy to deprioritize when the operational demands are high.
What was genuinely easier: getting alignment on direction when the reasoning is clear. I’d worried that at this scale, moving the organization would feel like pushing something very large and heavy. What I found is that people who understand why something matters move in that direction fairly readily, even when it’s hard, and the investment in the “why” pays back many times over in reduced friction. That surprised me a little. I expected more resistance to direction, and found more hunger for it.
None of this has made the work simpler, and I’ve stopped expecting it to. Scale adds genuine complexity that doesn’t resolve — it just becomes familiar. What I’ve gained isn’t a cleaner model of leadership. It’s a more honest one. And that’s a different thing entirely.