Dont Plan, Speculate

Leaders who cling to detailed plans are trying to control uncertainty with a false sense of security. The article argues that speculation - forming hypotheses with incomplete information - should replace rigid roadmaps. By making speculation a core phase, teams stay humble, ready to pivot, and can treat deviations as signals rather than mistakes.

The shift from "plan" to "speculate" changes language and behavior. Calling something a requirement hardens expectations, while labeling it a story or speculation invites evolution. When teams view deviations as clues, they can run disciplined experiments, as echoed by thinkers like Rita McGrath and Amy Edmondson, turning uncertainty into learning opportunities.

Wish-based planning and aggressive deadline cuts create cascading dysfunction: over-capacity, rushed testing, fragile code, and reward structures that praise grit over honesty. The article cites real-world fallout where impossible promises are praised and early warning signals are punished, entrenching toxic cycles.

Cultural surgery means leaders stop demanding rigid timelines and instead surface hard truths, reshaping roadmaps mid-flight as learning events. This creates psychological safety, aligns capacity with demand, and builds a resilient system where teams can experiment without fear.