Workflow · Management and operations

Pressure-test a business plan or decision with AI

Find the weak points before someone else does. AI challenges your plan; you make the decision.

Try with checksIt is worth trying only with the checks on this page.

For: Managers and founders, before they commit to something

Go to the steps Test it on your own work

What the evidence says

Studied directly. Studies look at this task or something very close to it.

Business advice from AI: not enough evidence yet (evidence strength 0 of 5)

Too few studies to rate. The rating page shows that AI business advice can help some owners and hurt others, so don't simply follow it.

This workflow itself is our recommended way of working, not a tested method. Studies searched to 2 November 2026.

Before you start

Write your plan down, even roughly. A plan in your head can't be tested.
Take out anything confidential, such as unannounced deals or staff names, unless your employer has approved the tool for it.

The steps

Replace the words in square brackets with your own. Stay in the same chat for the next prompt, unless a step says otherwise.

You
Write the decision, your reasons, your numbers and what would make you change your mind.

Ask it to attack the plan. By default AI tends to agree with you.

Prompt

Act as a sceptical adviser. Do not encourage me. Here is a decision I am about to make: [decision]. My reasoning and numbers: [paste].

First, check my arithmetic. Flag anything that needs legal or employment advice. Then give me: (1) the assumptions that matter most and how each could be wrong; (2) the three likeliest ways this fails; (3) what evidence I should get before deciding, and the cheapest way to get it; (4) options I haven't considered, including doing nothing.

Mark clearly what is your general reasoning and what is a fact I should verify.

You
Mark each point as: knew it, new and matters, or doesn't apply to us. Check any facts it gave.

Ask for the numbers to be stress-tested, and do the arithmetic yourself afterwards.

Prompt

Take my numbers and show what happens if sales are 30% lower, costs are 20% higher and it takes twice as long. Show each change alone, then together. If a number is missing, ask me. Show your working. I would stop if: [limit, such as cash I can lose]. At what point is that reached?

You
Talk the one or two most serious points through with someone who knows your business, then decide.

How to catch its mistakes

AI doesn't know your customers, staff or cash position. Treat its output as questions, not advice.
Every market size, competitor fact and benchmark needs a source you've opened.
If it agrees with everything, you've learned nothing. Ask it again to argue the opposite.
Check the arithmetic in your own spreadsheet.

When not to use this

Legal, tax, financial product or employment decisions. Use a qualified adviser, and use AI to prepare your questions for them.
The decision is already made and you want reassurance. It will probably give you some.
You're short of experience and are inclined to follow the advice as given. Ask someone experienced to look at it too.

Tools

A general AI assistant. Examples: ChatGPT, Gemini, Microsoft Copilot. We chose these because they are common in workplace software, not because they are the best. We leave out Claude products as examples, because we draft this site with Claude. AI assistants compared has them all, with dated facts. Use whichever your employer has approved. The steps work with any tool of this type. We take no money from AI companies.

Find out if it works for you

People often misjudge how much AI helps them. Try this on your next 10 similar tasks, letting a coin flip decide which ones use AI. What to measure: New, relevant risks you hadn't listed. Check after a few months whether they mattered.. Your results stay in your browser. Start the self-test →

If you manage people

Use it to prepare for a discussion, never to replace one. Decisions stay with named people.

Written by AI Adoption's editors as our own recommendation, last checked 5 November 2026. It has not been reviewed by an outside practitioner. Before publishing, we ran its prompts once on made-up samples with a second AI model, also from Anthropic. That is a check on the wording, not a test of whether the workflow works for you. Disclosure: AI Adoption uses AI tools in its research and editorial work, including Claude from Anthropic. No company has any say in this page. Reuse under CC BY 4.0. Spotted an error? Tell us.