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.mdin 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/. Claude Code uses it whenever a task fits.skills/ plan-stress-test/ SKILL.md