Free Agent Skill
Premortem
Run a premortem — imagine a plan has already failed and work backward to explain why, which surfaces risks that forward planning misses because it counteracts the social and psychological pressure to seem confident
Use when: The user is about to commit to a plan, launch, project, or big bet, when a group seems to have converged on optimism too quickly, or whenever premortem is explicitly requested. Best used before commitment, not after — if something has already failed, use postmortem-retro instead
Install this skill
Cursor, Claude Code and Codex
- Create a folder named `premortem`.
- Save the skill content below as `SKILL.md` inside that folder.
- Place the folder in `.cursor/skills/` for Cursor or `.claude/skills/` for Claude Code (or the equivalent path for Codex).
- Describe the task normally. Your agent loads the skill when its description matches.
Use this in ChatGPT or Claude (no code)
- Copy or download SKILL.md from this page (or put it in a folder named
premortem). - Zip that folder so the archive contains
premortem/SKILL.md. - In ChatGPT (Business, Enterprise, Edu or Healthcare), upload the zip under workspace Skills. In Claude.ai, add a Skill from the zip where your plan supports Skills.
- Describe the task in plain language — the skill loads when its description matches.
---
name: premortem
description: Run a premortem — imagine a plan has already failed and work backward to explain why, which surfaces risks that forward planning misses because it counteracts the social and psychological pressure to seem confident. Use this whenever the user is about to commit to a plan, launch, project, or big bet, when a group seems to have converged on optimism too quickly, or whenever premortem is explicitly requested. Best used before commitment, not after — if something has already failed, use postmortem-retro instead.
---
# Premortem
Teams that feel good about a plan tend to suppress doubts — voicing
concern feels like disloyalty or pessimism. A premortem removes that
pressure by making failure the assumed starting point, which makes
raising risks feel like the *helpful* thing to do rather than the
negative thing.
## The technique
Frame it exactly like this, don't soften it: **"It's [some point in the
future]. This has failed completely. What happened?"**
Then generate specific, concrete reasons — not vague ones. "It failed
because of poor execution" is not a premortem finding. "The vendor missed
the integration deadline by six weeks because nobody owned the
dependency" is.
Push for a real list, not one obvious answer:
1. Generate at least 5-8 distinct failure stories before evaluating any
of them. Breadth first, judgment second — evaluating too early kills
the quieter, weirder failure modes that turn out to matter most.
2. For each one, ask: is this preventable, detectable early, or just a
risk we accept? Sort them into those three buckets.
3. For "preventable," name the specific change to the plan now.
4. For "detectable early," name the leading indicator to watch for and
who's watching it.
5. For "accept," say so explicitly rather than letting it go unspoken —
an accepted risk that's written down is very different from one nobody
noticed.
## Common failure categories worth checking explicitly
- **Dependency failure** — something outside your control that the plan
quietly assumes will go right.
- **Timeline compression** — the plan assumed the best case for how long
things take, not the typical case.
- **Adoption/behavior** — the plan assumes people will act differently
than they have before, without a mechanism forcing that change.
- **Second-order reaction** — a competitor, regulator, or stakeholder
responds in a way the plan didn't model.
- **Silent single point of failure** — one person, system, or assumption
that everything else quietly depends on.
## Output
A short list of concrete failure stories, sorted into
prevent/detect/accept, with the plan changes that follow from the
"prevent" bucket stated explicitly. Don't just list risks — say what
changes about the plan as a result.
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