The roadmap that survives a quarter
Most roadmaps are obsolete by week six. The few that survive aren't more accurate — they're built around a different unit.
Roadmaps that list features by quarter age badly. By week six, three priorities have shifted, two features turned out harder than expected, and customer requests have changed the picture. The roadmap becomes a document everyone politely ignores.
Plan in bets, not features
A bet is a statement of intent with a measurable outcome and a cost ceiling. "We will move activation from 30% to 45% by end of Q2, and we're willing to spend two engineers for six weeks to find out." That survives changes in tactics because the goal stays stable.
Revise on cadence, not on news
Set a fixed cadence — monthly or every six weeks — when you revise. Between revisions, defend the bets. This reduces the whiplash where every customer call rewrites the plan.
Plans don't fail because they're wrong. They fail because they assumed they'd be right.