It doesn’t take long in any engineering team to notice the differences: some people itch for a blank canvas, some thrive turning chaos into order, and some see maintenance as an act of craft, not a chore. Simon Wardley’s Pioneers, Settlers, Town Planners gives these names, but you can spot them even if you’ve never seen the model.
Pioneers build when nothing exists. They break things and don’t mind if some of them fall apart later. Settlers pick up the raw, half-working pieces and start turning them into something others can use. Town Planners see the tangled results and lay foundations so the whole thing doesn’t collapse under its own weight. None of these roles are “better”; what matters is the match between the work and the people doing it.
Most companies ignore this. They try to run every team the same way, moving engineers across teams as if greenfield, brownfield, and legacy all require the same temperament. The result? Pioneers get bored and start rewriting for the sake of it, settlers drown in the process, town planners are handed new product spikes and told to “think outside the box.” Progress slows, people quietly leave.
What works better is noticing which phase your product or platform is actually in and tuning your teams to fit. Early on, you need people who will move without a map. As things take shape, you need folks who’ll knock rough edges off and turn wild ideas into steady delivery. When scale and reliability matter, you need planners who get a kick out of making things boring, stable, and safe.
Every org is a mix of invention, refinement, and maintenance. The biggest gains come from lining up the right people with the right kind of problems. Most of the time, we talk about team “fit” or “culture.” Maybe it’s simpler than that: some people are born to start fires, some to contain them, some to build fire stations.
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