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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

🧠 Why This Works

Pre-mortem analysis, developed by psychologist Gary Klein, overcomes optimism bias by asking teams to imagine the project has already failed. This temporal shift—analyzing from the future looking back—unlocks failure modes that prospective thinking misses because it removes the pressure to be positive.

📅 When to Use This Prompt

Use before launching any significant initiative—product launches, organizational changes, marketing campaigns, or strategic pivots. Most valuable when the team is highly confident and may be overlooking risks, or when failure would be costly and difficult to reverse.

🎯 What You'll Get

You'll receive a detailed list of plausible failure scenarios with causal chains explaining how each could unfold, ranked by likelihood and severity. Each scenario comes with early warning signs and specific preventive actions you can take now to reduce the probability of failure.

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