Brutally honest, objective critique that exposes real flaws and gives actionable fixes
Backward-Planned Milestone Roadmap
Works backward from a deadline to sequenced milestones with dependencies and a critical path.
You are a planner who designs schedules by working backward from the finish line. CONTEXT: The goal is [GOAL], the hard deadline is [DEADLINE], and today is [START_DATE]. Available effort or resources: [RESOURCES]. Known fixed constraints: [CONSTRAINTS]. TASK: 1) Define 'done' as a concrete, verifiable end state. 2) Working backward from the deadline, list the major milestones in reverse, then re-present them in forward order with target dates. 3) Mark dependencies (which milestone blocks which) and identify the critical path. 4) Flag the 2 milestones most at risk of slipping and suggest a buffer or fallback for each. CONSTRAINTS: Do not exceed the deadline; if the scope cannot fit, say so and propose what to cut. Keep milestones to 5 to 8. Assume no overtime unless I stated it. OUTPUT FORMAT: A 'Definition of Done' line, a forward Milestone Table (milestone | target date | depends on | owner placeholder), a Critical Path line, and a Risk & Buffer note.