The Premortem
Skill File
The exact prompt + 3-part framework I use to break my own plans before I build them.
Most people ask Claude "what could go wrong?" and get back five generic risks. This flips the frame. Claude stops cheerleading and starts running the autopsy.
The Autopsy
Set the scene: it's six months from now and your plan failed badly. Claude reverse-engineers the chain of events. Not "could fail" — "did fail. Walk me through how."
The Hidden Assumption
The one assumption your plan quietly depends on — the thing so obvious you forgot it was an assumption. Surface it, name it, then ask what breaks if it isn't true.
The Rebuild
Claude returns a hardened version of your plan with the weak spots fixed, plus an early-warning checklist of signals to watch for in the first 30 days. This is the step most premortem prompts skip.
Copy this entire block. Paste it into Claude. Then paste your plan where it says [your plan here].
Triple-click to select the block above ↑
Open Claude. Web, Code, or API — works the same.
Paste the prompt. Replace [your plan here] with your actual plan. Be specific — vague plans get vague autopsies.
Run it. Read it. Save the checklist. The early-warning signals are the part most people throw away. Don't.
Save this as a Claude Project or skill so you can run it on every plan you ship. The first time it catches a fatal flaw on day one, the workflow pays for itself.
Send it to a founder
who needs it.
And follow along for more Claude workflows that actually ship.
@mikemeansbusiness_ai →Mike Means Business · Claude workflows for operators