Prioritization & Roadmaps
🚧 ExpandingPrioritization is where strategy meets reality and someone has to say no. Everything looks important when it’s on a list; the hard part is holding two genuinely good options side by side and choosing — then defending that choice to the people whose pet feature didn’t make the cut. (One of the perennial trade-offs hiding in that list is paying down tech debt versus shipping the next feature.) A roadmap is just that set of choices made visible, with the why attached so people can trust it instead of relitigating it every week.
When this page is filled in, it’ll cover how to weigh effort against impact without hiding behind a fake-precise scoring spreadsheet; how to say no to good ideas so you can say yes to the great ones; how to build a roadmap that communicates intent without making promises about dates you can’t keep (the scope, resources, and time levers are how you negotiate those promises honestly); and how to keep the roadmap a living document rather than a contract carved in stone. Until then, the Go Deeper links carry the weight — start with Escaping the Build Trap if your roadmap is really just a feature factory in disguise.
📚 Go Deeper
Books
- Escaping the Build Trap — Melissa PerriThe book to read before you build another roadmap — it reframes prioritization around outcomes instead of feature output.
- Shape Up — BasecampA concrete alternative to the endless backlog — fixed appetites, betting on what's worth a cycle, and no roadmap promises you can't keep.
- An Elegant Puzzle — Will LarsonLarson on systems for prioritizing engineering investment across competing demands — practical at the team and org level both.