Run the pre-mortem before the big bet
We run post-mortems after things break, when the only thing left to do is assign the lesson. The pre-mortem does the same work while it still matters. It's twenty minutes, it needs no software, and it will change at least one thing about your next big decision.
How to run it
Gather the people close to the decision. Set the scene out loud: "It's a year from now. This bet failed, clearly and expensively. Everyone already knows it did." Then ask one question and write down every answer without arguing: "What went wrong?"
The framing matters. Asking "what could go wrong" invites polite, hedged risks. Asking a room to explain a failure that has already happened gives people permission to say the real thing — the concern they'd never have raised while everyone was still optimistic.
Sort the answers into two piles: risks you can reduce now, and risks you'll simply watch. Pick the top one from the first pile and do something about it this week. That single move, made before the bet instead of after, is the whole return on the twenty minutes.
