Pre-Mortem Analysis
Imagine your project has already failed. Work backward to figure out why – and prevent it now.
Prompt
I am about to:
[DESCRIBE YOUR DECISION, PROJECT, OR INITIATIVE]
Perform a Pre-Mortem: It is one year from now and this has failed
spectacularly.
1. What are the 6 most likely reasons it failed?
2. For each, what early warning signs should I watch for?
3. Rank them by likelihood AND severity
4. For the top 3, what specific action can I take NOW to prevent them?
5. What is the one failure mode I'm almost certainly not thinking about?
Example
Input:
I am about to launch a SaaS product with a team of 3, bootstrapped,
targeting small marketing agencies.
Output (abbreviated):
1. Ran out of money before finding product-market fit
Warning signs: Low trial-to-paid conversion after month 2,
customer calls revealing "nice to have" not "must have" sentiment
Likelihood: High | Severity: Critical
2. Built features nobody asked for instead of selling
Warning signs: Sprint boards full of ideas, empty CRM pipeline,
more GitHub commits than customer conversations
Likelihood: High | Severity: High
...
The one you're not thinking about: Your team of 3 has an unspoken
disagreement about what success looks like. One person wants VC scale,
another wants lifestyle business. This will fracture every decision
by month 6.
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