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Run a Pre-Mortem Before Your Plan Fails
Imagine your project already failed — then work backward to find the causes and prevent them now
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I want to run a pre-mortem on [PROJECT/PLAN/DECISION]. The plan: - What we're doing: [DESCRIBE] - Timeline: [WHEN] - Success looks like: [DEFINE SUCCESS] - Team/resources: [WHO IS INVOLVED] - Current confidence level: [HIGH / MEDIUM / LOW] Imagine it is [TIMELINE END DATE]. The project has FAILED. It's a disaster. Now work backward: 1. FAILURE SCENARIOS (generate 8-10) For each, write a realistic "news headline" of what went wrong. Group by category: - Execution failures (team, process, quality) - Strategic failures (wrong market, wrong timing, wrong approach) - External failures (competition, regulation, economy) - People failures (turnover, conflict, misalignment) - Unknown unknowns (what we didn't even consider) 2. ROOT CAUSE ANALYSIS For the top 5 most likely failure modes: - What sequence of events leads to this failure? - When does the first crack appear? (earliest warning sign) - Who notices first? (and do they have the power to act?) - Why didn't we prevent it? (what made us blind to it?) 3. PREVENTION PLAYBOOK For each top failure mode: - One action to take THIS WEEK to reduce the risk - One metric to monitor that would catch it early - One person who should own this risk - The decision trigger: "If [X happens], we will [Y]" 4. KILL CRITERIA Define 3 clear conditions under which you should STOP the project entirely: - What data would prove this is not working? - At what point is it braver to quit than continue? - Who has the authority to call it? 5. CONFIDENCE UPDATE After this pre-mortem: - Has your confidence level changed? - What's the ONE thing that could prevent 80% of failures? - Should you proceed, adjust, or abandon?
#decision-making#strategy#pre-mortem#before#your
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chatgptclaudegemini
💡 Pro Tips
- •Pre-mortems work better than risk assessments because 'imagining failure' activates different thinking than 'listing risks'
- •Do this with your team, not alone — different people see different failure modes
- •The most valuable output is the kill criteria — knowing when to stop is harder than knowing when to start
✨ Example Output
Project: Launch an online course in 3 months Success: 200 paid students at $299 = $59,800 revenue FAILURE HEADLINES: 1. "Course Creator Launches to Crickets — Only 11 Students Sign Up" 2. "Students Demand Refunds After 60% Drop-Off by Module 3" 3. "Competitor Launches Similar Course at Half the Price, Two Weeks Earlier" 4. "Creator Burns Out Trying to Build Course While Working Full-Time" 5. "Technical Disaster: Platform Crashes on Launch Day, Loses Student Data" ROOT CAUSE ANALYSIS — #1 "Launches to Crickets": - Sequence: Built course in isolation → no audience building → launched to cold traffic → spent $2K on ads → 0.5% conversion → 11 students - First crack: Week 2 — email list has only 47 subscribers - Who notices: Creator, but rationalizes "I'll market harder at launch" - Why blind: Excitement about content creation masks the marketing gap PREVENTION PLAYBOOK: - THIS WEEK: Start a free email mini-course to validate demand and build list - METRIC: Email list size — need 2,000 subscribers by launch for 200 students (10% conversion) - OWNER: You (non-delegable) - TRIGGER: "If email list is below 500 by week 6, delay launch by 1 month and focus on audience" KILL CRITERIA: 1. If pre-sale (offered at 50% off) gets fewer than 30 buyers → demand is insufficient 2. If 3 beta testers drop off at the same module → content needs fundamental rework 3. If total time investment exceeds 400 hours before launch → scope is too large, simplify