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opelplepleopelpleple/meta-skills/pre-mortem/SKILL.md

pre-mortem

Skill0 starsChanged 5 months agoMITView on GitHub

Imagines the plan has already failed six months in the future, then works backwards to enumerate every reason why — surfacing risks that optimism and momentum normally hide. Use this skill when the user is finalizing a plan, launch, migration, hire, or big decision and asks "what could go wrong?", "review my plan", "what am I missing?", "poke holes before we commit", or is about to commit to something expensive or hard to reverse. Pairs with grill-me (which stress-tests at the start); pre-mortem assumes failure has happened and reasons backward.

30 other projects use a version of this.

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The file

We split this skill into the rules it gives an agent

1 rule. 0 are common, 1 is distinctive, and 0 are very specific to this project.

  • 0

    Common

    Most of the 23 edited versions we read keep these.

  • 1

    Distinctive

    This author's own choices. Worth a look.

  • 0

    Very specific

    Tied to their project's names, files or tools. Probably skip.

  • Common
  • Distinctive
  • Very specific
  1. Distinctive:

    Only technical risks; the killers are often people, ownership, and false assumptions.

    line 43

“Common” is measured: kept by at least 6 in 10 of the 23 edited versions of this file we could read. “Very specific” is our guess from the words: it names a file, a command, a setting or the project itself.

Keep what fits and drop the rest. Your version, ready for your agents.
Files
SKILL.md

Pre-Mortem

Assume it's six months from now and the project failed. The question isn't "could it fail?" — it's "it failed; now, why?" That framing unlocks risks people won't admit while they're still hopeful.

When to use

  • Finalizing a plan, launch, migration, or roadmap before committing.
  • High-stakes, hard-to-reverse decisions (hire, vendor lock-in, public launch).
  • The team is confident and aligned — exactly when blind spots hide.
  • Right before a go/no-go gate.

When NOT to use

  • Early ideation where you're still generating, not committing.
  • Trivial or easily reversible decisions (don't pre-mortem a font choice).
  • The team is already demoralized — this can tip into doom; reframe toward mitigation fast.
  • You have no plan yet — there's nothing concrete to fail.

The method

  1. Set the scene out loud: "It's [date, ~6 months out]. The project shipped but failed / never shipped. It's a clear, undeniable failure." Make it vivid and concrete.
  2. Generate failure stories independently first — list as many distinct ways it died as you can before discussing any. Quantity beats polish here.
  3. Cover the categories: technical, people/team, scope/timeline, external/market, dependencies, assumptions that turned out false, and "the boring thing nobody owned."
  4. For each failure, write the one-line obituary: "It failed because ___."
  5. Score each on likelihood x impact. Focus on high-impact, plausible failures, not exotic ones.
  6. For the top risks, name the earliest warning sign — what would you observe in week 2 or 4 that this is happening?
  7. Convert each top risk into a mitigation or a tripwire: prevent it, or define the signal that triggers a course-correction.
  8. Output: ranked risks, leading indicators, and concrete pre-commitments (what you'll do now, what you'll watch for).

What good looks like

  • At least one risk surfaces that nobody had said aloud before.
  • Risks are specific ("the third-party API rate limit kills our import at scale"), not generic ("scope creep").
  • Each top risk has an early warning sign and an owner.
  • The plan changes as a result — a mitigation added, scope trimmed, or a tripwire set.

Anti-patterns

  • Vague risks ("communication issues") that can't be watched for or prevented.
  • Listing only risks you already planned to handle (theater, not discovery).
  • Stopping at the scary list with no mitigations or tripwires.
  • Pre-mortem as veto — using it to kill a project rather than de-risk it.
  • Only technical risks; the killers are often people, ownership, and false assumptions.

Example

Plan: "Launch the new billing system on the 1st." Pre-mortem (it's the 1st of next quarter; the launch failed):

  • "It failed because customers were double-charged during the cutover." (High impact, medium likelihood.) Early sign: mismatched totals in the dry-run reconciliation. Tripwire: any reconciliation delta > $0 in staging blocks launch.
  • "It failed because the old system's edge-case discounts weren't migrated and finance found out in week 3." Early sign: discount count differs between systems. Mitigation: diff discount records before cutover; assign an owner.
  • "It failed because nobody owned customer comms and support drowned." Sign: no comms draft exists 1 week out. Mitigation: assign comms owner today. Result: launch gated on zero reconciliation delta, a discount diff added to the checklist, and a named comms owner.

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