Leadership

Somewhere around year eight or nine, the question stops being hypothetical. Both paths are available. The organisation is large enough that both exist as genuine roles, not just titles. You have to actually decide. I’ve been close to this decision twice. The first time, at the startup, it was resolved by circumstance — there was no EM role to take, so staff-track it was. The second time, in a larger organisation, it was a real choice. Here’s the framework I used and what I’d change about it. ...

At the large US technology company, no single team controls the entire system. A feature that touches payments, identity, and platform teams requires coordination across three codebases, three on-call rotations, and three sets of priorities. Getting technical alignment across teams without creating bureaucratic overhead is an active engineering problem. ...

At the large US technology company, RFCs circulate widely. A proposal touching platform infrastructure might be read by engineering leadership, a dozen affected teams, security review, and a product counterpart — none of whom share the same technical context. Writing for a narrow expert audience is one skill. Writing for a wide, mixed audience is a different one. ...

In the years at the European financial technology firm, the engineering organisation went through three significant restructuring events: a change in engineering leadership, a shift from functional to product-aligned teams, and a consolidation of two separate engineering groups. Each one produced the same kind of disruption and the same kind of opportunities. Org change is uncomfortable. It’s also underanalysed. Most engineers treat it as something happening to them, not something to navigate actively. ...

The term “technical debt” was coined by Ward Cunningham specifically as a financial metaphor. Debt isn’t inherently bad — it’s a tradeoff: you get something now in exchange for a future obligation. When the metaphor is understood, the management of technical debt becomes clearer. When the moral framing replaces the financial one, it becomes a guilt-driven cycle that helps nobody. ...

I was promoted to tech lead at the startup in early 2020. The team was five engineers, including me. My previous experience managing people: none, unless you count mentoring a couple of interns. The first month was humbling. The second month was better. By the third month I had a clearer mental model of what the role actually required and how it differed from what I’d been doing before. ...