Every engineering team has a roadmap. Most engineering roadmaps are wrong. Not in a surprising way — in a predictable way that reflects structural problems in how they’re created. After doing roadmap planning at two companies at different scales, here’s what I think actually works and why most roadmaps fail. ...
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. ...
Over two years running engineering hiring at the firm, we made about twenty senior engineering hires. Some were transformative — engineers who raised the quality of everything they touched. Some were neutral — competent contributors who did what was asked and not much more. A few were net negatives. Looking back, the correlation between interview performance and outcome was weaker than I’d expected. The things that predicted good hires were visible in the interview, but we weren’t consistently measuring them. ...
The startup had been good. We’d grown from twelve people to forty, shipped something real, and the technical foundations were solid. But the Series B had brought in a new leadership layer, the founding team’s velocity calculus had changed, and I found myself doing more coordination than building. I’d been at this inflection point before — at the institution, actually — and I recognised what came next. The new role was at a well-established European financial technology firm. Structured, profitable, engineering-first culture, around 400 people. Not a startup. Deliberately not a startup. ...
The fintech startup started using RFCs (Request for Comments documents) when we hit seven engineers and decisions stopped being made naturally in conversation. Before RFCs, we’d build something, present it, discover disagreement, and partially rewrite. The disagreement was always there — we just discovered it late. RFCs in theory: write down what you’re proposing before building it, get feedback, align, then build. RFCs in practice, initially: long documents that people didn’t read, discussions that went in circles, and decisions that weren’t really made. The format that fixed it took six months to evolve. ...
The standard startup narrative is that small teams move fast because they cut process. No PRD approval chains, no design committee sign-off, no six-week delivery timelines. Just engineers and a product idea, shipping. That narrative is true as far as it goes, and incomplete in important ways. The startup I joined from 2019 to 2021 was fast for reasons that went beyond “we skipped the bureaucracy.” Understanding those reasons changed how I think about engineering productivity in any context. ...
The fintech startup hit the platform question about eighteen months in. We had product-market fit, we were growing, and the engineering team was doubling every six months. The systems that had worked at ten engineers were showing strain at twenty-five. The question became: dedicate engineering time to platform work, or keep all capacity on product features? This is a hard question. The people who get it right aren’t smarter — they’re clearer about what they’re actually trading off. ...
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. ...
Three months into the startup, the prototype was working and investors were asking for a production timeline. We had a Postgres database, a Python script doing the core business logic, and no infrastructure to speak of. The decision: rewrite in Go, build proper infrastructure, or ship the Python and iterate? And if we rewrite, what does “proper infrastructure” mean when you have six engineers and four months of runway? ...
I left a well-paying, intellectually interesting job at a large financial institution to join a company with fewer than twenty people and less than a year of runway. My colleagues thought I’d lost perspective. My family was diplomatically concerned. Here’s the honest version of the reasoning. ...