Find the hidden risks in a plan

A plan looks fine but something feels off. Get what could go wrong and a simple way to prevent each problem.

Updated 17 Oct 2026

The prompt · ChatGPT

Check my plan for hidden risks.

My plan: [paste it: a trip, a party, a move, a project, a launch]
Date it happens: [date]
What matters most: [e.g. staying on budget, everyone safe, on time]

Imagine it's the day after and the plan went badly wrong. Work backwards:
Before you start, ask me up to 3 short questions if anything important is missing. Wait for my answers.

1. List the 5 most likely things that went wrong.
2. Rate each one: how likely (low/medium/high) and how bad (low/medium/high).
3. For each, give one step I can take now to prevent it.
4. For the top 2, give a plan B.
5. Tell me anything my plan doesn't mention that it should.

Be practical and specific. Don't invent facts about my plan; ask if unsure. UK English.

Stay in this ChatGPT chat. Do not turn on apps or connectors, and do not use memory from another chat.

A short example

Fill the blanks, then paste. paste it: a trip, a party, a move, a project, a launch: a short note you already have. date: a short note you already have. Leave the rest of the prompt as written.

The prompt · Claude

Check my plan for hidden risks.

My plan: [paste it: a trip, a party, a move, a project, a launch]
Date it happens: [date]
What matters most: [e.g. staying on budget, everyone safe, on time]

Imagine it's the day after and the plan went badly wrong. Work backwards:
Before you start, ask me up to 3 short questions if anything important is missing. Wait for my answers.

1. List the 5 most likely things that went wrong.
2. Rate each one: how likely (low/medium/high) and how bad (low/medium/high).
3. For each, give one step I can take now to prevent it.
4. For the top 2, give a plan B.
5. Tell me anything my plan doesn't mention that it should.

Be practical and specific. Don't invent facts about my plan; ask if unsure. UK English.

Stay in this Claude chat. Do not use a connector, and do not open a project that already holds someone else's files.

A short example

Fill the blanks, then paste. paste it: a trip, a party, a move, a project, a launch: a short note you already have. date: a short note you already have. Leave the rest of the prompt as written.

You paste your plan, however rough.

The assistant asks what matters most, then imagines the plan has gone wrong and works backwards.

You get the top risks ranked, with a prevention step and a plan B for each.

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What happens

Use Claude to find the hidden risks in a plan

A plan looks fine but something feels off. Get what could go wrong and a simple way to prevent each problem.

Tools

Paste the prompt, fill the blanks, copy the draft.

Claude — required. Drafts from the text you paste. Nothing is sent.

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