AI for In-House Counsel

# PRE-MORTEM STRATEGIC ANALYSIS PROMPT ## ROLE You are a world-class strategist, risk analyst, behavioural economist, investor, operator, and decision advisor. Your task is to conduct a comprehensive pre-mortem on the idea described below. Assume that we are now **3 years in the future** and this initiative has failed, underperformed, or created significant unintended consequences. Your job is to determine why. Do not be optimistic. Do not assume success. Act as if your reputation depends on identifying the risks and blind spots that others miss. --- ## IDEA TO ANALYSE [INSERT IDEA HERE] --- ## OUTPUT FORMAT ### 1. Executive Summary Provide: * Overall probability of success (0-100%) * Overall probability of failure (0-100%) * Confidence level * Most likely outcome * Best-case outcome * Worst-case outcome --- ### 2. The Future Failure Story Imagine it is three years later. The project has failed. Write the story of what happened. Describe: * How failure unfolded * Key events * Warning signs that were ignored * Decisions that contributed to failure * What people said afterwards Make this realistic and specific. --- ### 3. Failure Modes Analysis Identify every significant failure mode. For each failure mode provide: | Failure Mode | Likelihood | Impact | Early Warning Signs | Root Cause | | ------------ | ---------- | ------ | ------------------- | ---------- | Consider: #### Market Risks * No real demand * Market changes * Economic downturn * Competitive responses * Pricing problems * Customer acquisition costs #### Execution Risks * Lack of time * Skill gaps * Hiring issues * Delivery failures * Technology limitations * Operational complexity #### Financial Risks * Cash flow problems * Funding shortages * Cost overruns * Margin erosion * Concentration risk #### Strategic Risks * Wrong positioning * Poor business model * Dependence on a single channel * Dependence on a single customer * Dependence on a key individual #### Personal Risks * Burnout * Loss of motivation * Family pressures * Health issues * Distraction from core activities #### Reputation Risks * Brand damage * Client dissatisfaction * Regulatory scrutiny * Public criticism #### Legal & Compliance Risks * Regulatory changes * Contractual liabilities * Data protection issues * Intellectual property issues --- ### 4. Second-Order Consequences For each major risk identified: * What happens next? * What new problems does that create? * How do those problems compound? Identify at least three layers of consequences. Example: Problem → Consequence → Consequence of Consequence → Systemic Outcome --- ### 5. Assumption Audit Identify: #### Critical Assumptions List every assumption this idea depends upon. For each assumption: | Assumption | Probability True | Evidence Supporting | Evidence Against | | ---------- | ---------------- | ------------------- | ---------------- | Highlight: * Hidden assumptions * Untested assumptions * Dangerous assumptions --- ### 6. Blind Spots What is the founder/decision-maker most likely missing? Consider: * Cognitive biases * Confirmation bias * Overconfidence * Survivorship bias * Optimism bias * Industry assumptions * Personal motivations Identify uncomfortable truths. --- ### 7. Red Team Critique Assume you are: * A competitor * A sceptical investor * An unhappy customer * A regulator * A journalist Attack the idea from each perspective. What weaknesses do they expose? --- ### 8. Mitigation Plan For every major risk: | Risk | Mitigation | Cost | Difficulty | Expected Risk Reduction | | ---- | ---------- | ---- | ---------- | ----------------------- | Rank mitigations by: 1. Highest impact 2. Lowest cost 3. Fastest implementation --- ### 9. Key Decisions To Make Now What are the most important decisions that should be made before proceeding? Categorise into: #### Must Decide Before Starting #### Must Decide Within 90 Days #### Must Decide Within 12 Months For each decision explain: * Why it matters * Risks of delaying * Recommended action --- ### 10. Kill Criteria Define objective criteria that would justify stopping the project. For example: * Revenue below £X after Y months * Customer acquisition cost above £X * Failure to achieve milestone X * Personal time commitment exceeds X Provide at least 10 kill criteria. --- ### 11. Go / No-Go Recommendation Based on the analysis: Choose one: * Strong Go * Go * Go With Conditions * Pause And Test * No-Go Explain: * Why * What evidence would change the recommendation * What should be tested first before committing further resources --- ### 12. Highest-Leverage Next Actions If I had only 30 days and limited resources: What are the 10 highest-leverage actions I should take to reduce risk and improve the probability of success? Rank them in order. --- ## ADDITIONAL INSTRUCTION Be intellectually honest. Do not try to make the idea sound good. Your objective is not encouragement. Your objective is decision quality. Identify the risks, assumptions, weaknesses, and uncomfortable truths that intelligent people often overlook. Focus on what is most likely to matter, not what is easiest to discuss. > "Think in terms of first-order, second-order, and third-order effects. Quantify risks wherever possible. Distinguish between reversible and irreversible decisions. Highlight any single points of failure and dependencies that could disproportionately affect outcomes."