Lesson 224 · 2 min
Asking AI to critique your plan
Ask the AI to find the weakest points and likely failures in your plan, and it starts to act like a tough sparring partner.
If you ask "Is my plan good?", most chatbots say yes. They tend to agree with the person asking. That feels nice and teaches you nothing.
Change the question. Ask for the three weakest assumptions, the most likely reason the plan fails, or what a sceptical manager would ask. Give it a role, like an experienced investor or a cautious finance director.
A useful trick is the "pre-mortem": tell the AI to imagine the plan failed six months from now and to explain what went wrong. People and chatbots find risks more easily when they imagine failure as already happened.
You decide which points are real. Some critiques will be generic. Keep the ones that make you think and fix your plan for those.
Do it now
Run a pre-mortem
- 1. Write your plan in five to ten lines.
- 2. Run the prompt below.
- 3. Pick the two most realistic risks and add a step to your plan for each.
Here is my plan: [PASTE]. Imagine it is six months later and the plan has failed. Explain the 5 most likely reasons it failed, most likely first. For each, suggest one early warning sign and one step I could add now to prevent it. Be direct; do not praise the plan.
Quick check
Keep going
Next →Writing a decision memoWords from this lesson
- Sycophancy
- An AI's tendency to agree with you or flatter your ideas instead of telling you where you are wrong.
- Role prompting
- Starting a prompt by telling the AI who to act as, such as an experienced editor, to shape tone and focus.