Pre-Mortem Framework
Use the pre-mortem technique to imagine your decision failed, then work backwards to identify risks and create mitigation plans before committing.
Imagine your decision has failed spectacularly, then work backwards to identify what went wrong and how to prevent it.
What is a pre-mortem?
A pre-mortem is the opposite of a post-mortem. Instead of analyzing failure after it happens, you imagine it in advance.
You assume your decision has failed, then brainstorm all the reasons why it might have failed.
This surfaces hidden risks, blind spots, and assumptions you haven't questioned.
How to run a pre-mortem
- Set the scene: "It's 6 months from now. I made this decision and it was a disaster."
- Brainstorm failures: List every possible reason why it failed. Be specific and brutally honest.
- Prioritize risks: Which failures are most likely? Which would hurt the most?
- Mitigate proactively: For each major risk, create a plan to prevent or reduce it.
- Decide with eyes open: Now make your decision knowing what could go wrong and how to avoid it.
Example: Accepting a startup job offer
Scenario: "It's 6 months in and I deeply regret joining this startup."
Possible failures:
• Company ran out of runway and shut down.
• My manager overpromised and the role isn't what was described.
• Culture is toxic and I'm miserable.
• Equity is worthless because of bad cap table terms.
• I miss the stability and structure of my old job.
Mitigation strategies
- Do deeper due diligence: check runway, ask about burn rate, research founders.
- Get job expectations in writing; clarify success metrics for first 90 days.
- Do reference checks with former employees to understand culture.
- Review equity offer with a lawyer or experienced advisor before accepting.
- Negotiate terms (remote work, severance) that give you more flexibility if things go south.
When to use a pre-mortem
- High-stakes decisions with significant downside risk.
- When you're excited about a decision and might be overlooking red flags.
- Before committing to irreversible choices (relocation, career change).
- When making decisions under uncertainty with many unknowns.
Why it works
Research shows teams using pre-mortems identify 30% more risks than standard planning.
It gives you "permission" to voice doubts without being negative or unsupportive.
It forces you to think probabilistically: "What are the ways this could fail?" instead of assuming success.