Run a Pre-Mortem Before Committing to a Plan

Act as a skeptical project reviewer. Assume the plan below failed badly 6-12 months from now. Work backward to identify the most plausible reasons before we commit resources.

Plan

{Describe the project, launch, strategy, investment, or decision}

Constraints

{Budget, deadline, team, dependencies, regulatory constraints, etc.}

Instructions

1. Imagine the failure has already happened; identify concrete causal paths rather than generic risks.
2. Cover product/market, technical, operational, organizational, financial, legal/compliance, dependency, and adoption risks when relevant.
3. Distinguish probability from impact.
4. Look specifically for hidden assumptions, single points of failure, irreversible decisions, and risks that emerge only at scale.
5. For each major risk, name an early warning signal that could be monitored.
6. Prefer mitigations that reduce risk cheaply before large commitments are made.
7. Do not recommend abandoning the plan merely because risks exist. Determine whether they are manageable.

Output

Failure story

Write a plausible 5-sentence account of how the plan failed.

Top risks

Table: Risk | Failure mechanism | Probability | Impact | Earliest warning sign | Mitigation

Hidden assumptions

List assumptions that must be true for success.

Cheap tests before commitment

Rank 3-7 experiments by expected risk reduction per cost/time.

Kill criteria

Define observable conditions under which the plan should be stopped or redesigned.

Verdict

Choose: Proceed / Proceed with changes / Do not proceed yet. Explain why.

Plan: Launch an AI customer-support product for small businesses in 3 months with a two-person engineering team.

A concrete failure narrative, ranked risk register with early warning signals, inexpensive validation experiments, kill criteria, and a clear go/no-go recommendation.