Skill: The Pre-Mortem Memo. Kill Bad Decisions Before You Fund Them
A reusable AI move that surfaces the top ways a decision fails BEFORE you commit money or people to it. Use it on any hire, purchase, or new offer.
What it is: A pre-mortem is a thinking move where you assume the decision already failed, then work backward to list why. AI makes it fast and unflinching. It has no ego in your plan and won't soften the bad news. This is one of the highest-leverage 10-minute uses of AI for an operator.
Why it matters: Most expensive mistakes weren't unknowable. They were unspoken. The failure mode was sitting in someone's gut, but nobody said it in the room. A pre-mortem forces those quiet risks onto the page where you can price them, mitigate them, or walk away.
When to use it:
- Before a hire over ~$60k all-in
- Before signing a lease, vehicle, or equipment purchase
- Before launching a new service line or offer
- Before a partnership or JV
- Anytime you feel 'mostly sure' but haven't tested the downside
How to run it:
Set the frame. Tell the AI: "It's 12 months from now and this decision has clearly failed. Here's the decision: [describe it in 4–6 sentences: the money, the people, the assumptions]. Write the post-mortem explaining exactly why it failed."
Demand specifics. Add: "Give me the 7 most likely failure causes, ranked by probability × cost. For each: the early warning sign I'd see in the first 60 days, and one concrete mitigation."
Stress the assumptions. Ask: "Which single assumption, if wrong, breaks this entire decision? How would I test it cheaply before committing?"
Human checkpoint (do not skip): Take the top 3 risks to the one person closest to that work: your ops lead, your bookkeeper, the tech who'll actually do it. Ask: "Which of these is most real?" Their answer is worth more than the whole memo.
Decide on paper. Write one line: "I'm proceeding because [X], and I've mitigated the top risk by [Y]. I'll kill it if I see [early warning sign] by [date]."
What it's worth: One avoided bad hire is $30k–$80k. One avoided bad lease is years of regret. Ten minutes of structured doubt is the cheapest insurance you'll ever buy.