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Decision MakingPremiumintermediate
4.7

Run a Pre-Mortem Before Your Plan Fails

Imagine your project already failed — then work backward to find the causes and prevent them now

Copy & Paste this prompt
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

Works with

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