or, What to Do When Decisions Keep Getting Stuck There’s a particular kind of stuckness that shows up on capable product teams. It doesn’t look like chaos. The calendars are full. Research is happening. Dashboards get updated. Customer conversations are logged and circulated. Everyone involved can explain their point of view clearly and back it up with evidence. And yet “decisions” keep reopening. The roadmap shifts without really changing. Priorities feel provisional. Plann

Planning season comes around like clockwork. Budgets, OKRs, capacity models, prioritization frameworks—the rituals of focus and alignment. On paper, it’s a time for clarity. In reality, it often feels like an annual stage play: certainty (captured neatly in PowerPoint) built on incomplete understanding. Every PM knows the pattern. The more polished the plan, too often the shakier the foundations beneath it. The Fiction of Certainty Most of what gets discussed in planning seas