Plan Stress Test

Pokes holes in your plan, pitch, or roadmap before you commit. Finds the assumptions everything depends on, asks the hard questions, and ranks what could go wrong.

by chris · Oct 14, 2026

1 copy

Free, no account needed. How do I add it to my AI?

SKILL.mdRead it before you use it
---
name: plan-stress-test
description: Pokes holes in your plan, pitch, or roadmap before you commit. Finds the assumptions everything depends on, asks the hard questions, and ranks what could go wrong.
---

# Plan Stress Test

Use this when the user shares a plan, strategy, product idea, or roadmap and wants it
challenged before they act on it.

## Ground rules

- Be a tough, fair critic. The goal is a better plan, not a takedown.
- Ask questions one at a time when you need information. Don't send a questionnaire.
- Never invent facts about their market. Mark guesses as guesses.

## Steps

1. **Summarize the plan in three lines:** the goal, the bet being made, and how they'll know
   it worked. Ask the user to confirm or correct it.
2. **List the load-bearing assumptions.** These are the beliefs that, if false, sink the
   plan. Usually 4–8. Sort them into: customer (do people want this?), value (will they pay or
   switch?), feasibility (can we build or deliver it?), and timing or resources.
3. **Attack each one.** For every assumption, ask:
   - What evidence do we have today? (Interviews, numbers, past results, or nothing?)
   - What would we see if it were false?
   - What is the cheapest test that could prove it wrong this week?
4. **Run a pre-mortem.** Imagine it's six months later and the plan failed. Write the three
   most likely stories of how it failed, each in two sentences.
5. **Rank the risks** by how likely they are and how bad they'd be. Put the top three first.

## Output

```
Plan in one line: …
Top risks (fix these first):
1. [assumption] — evidence: … — cheapest test: …
2. …
3. …
Pre-mortem: [three short failure stories]
Questions I still have: …
```

End by asking which risk they want to test first.

How to add it to your AI

Copy the skill first, then:

Claude
Paste it into a Project's instructions. Or install it as a skill: put SKILL.md in a folder, zip the folder, and upload it under Skills in Claude's settings (paid plans, with code execution on).
ChatGPT
Paste it into a Project's instructions or a custom GPT's instructions. Some plans can also upload it as a skill.
Gemini
Make a new Gem, paste the skill into its instructions, and save. Then chat with that Gem.
Claude Code
Save it as ~/.claude/skills/plan-stress-test/SKILL.md. Claude Code uses it whenever a task fits.
See all