Use it when you are

  • Choosing between job offers, or between staying and leaving
  • Deciding whether to hire, buy a tool, sign a lease or take on a client
  • Breaking a deadlock when you keep going back and forth between two options
  • Preparing a decision memo with the options and trade-offs laid out for someone else

Why this prompt works

Questions come before answers

A model given a decision and asked for advice will advise at once, on whatever partial picture it has. Round 1 restricts the reply to a restatement and up to five questions. The restatement alone is often useful: seeing the choice put in one sentence can show that you framed it too narrowly.

Your leaning is an input to be challenged

Models tend to go along with the preference a user expresses. Asking for your leaning openly and then requiring the strongest honest argument against it turns that tendency around. If the counter-argument does not move you, you can proceed with more confidence; if it does, better now than later.

The option set gets wider

People usually arrive with two options. Adding 'do nothing or wait' and a smaller trial version puts alternatives on the table that are easy to overlook when you are close to the choice, and a trial is often the cheapest way to learn what you are missing.

Effort matches the stakes

Not every choice deserves a matrix. Step A asks how reversible the decision is and tells the model to keep things short if it is cheap to undo, so the prompt does not turn a minor choice into a long exercise.

Scores are shown with reasons and unknowns

A total from a scoring table gives a false sense of precision. Here each cell carries its reasoning, unknowns are marked with a question mark, and the model is told to discuss the cells that drive the result, which keeps attention on judgment calls and missing facts.

How to use it

  1. State the decision and every option you are seriously considering, including the one you are embarrassed to want.
  2. List what matters to you in the outcome, in rough order of importance.
  3. Fill in your current leaning honestly; the counter-argument is only useful if it targets your real preference.
  4. Send the prompt, then answer the Round 1 questions in the same conversation. Say 'I don't know' where that is the truth.
  5. Correct the criteria weights in step C if they do not reflect your priorities and ask for the table to be redone.
  6. Act on the 'cheapest way to find out' suggestion before you commit, if the deadline allows.

AI model compatibility

ModelStatusNotes
ChatGPTExpected to workIf the model runs straight into the analysis instead of stopping after Round 1, reply: 'Stop. Ask your Round 1 questions first and wait.'
ClaudeExpected to workAnswer the Round 1 questions in a numbered list matching the questions so each answer is tied to the right one.
GeminiExpected to workKeep both rounds in the same conversation so the Round 2 analysis can draw on your answers.

“Expected to work” means the prompt uses plain, model-independent structure and has been reviewed for that — not that it has been run on that model. A model is marked Tested only when a test record is published below.

Worked example

Scenario: The owner of a small design studio deciding how to handle bookkeeping. Details are invented for illustration.

Example: filled-in prompt
# Role
You are a thinking partner helping me make a decision. You are not here to reassure me. Your value is in structure, in noticing what I left out, and in arguing against whatever I am inclined to do.

# The decision
- What I am deciding: Whether to hire a full-time bookkeeper or keep using an outside accountant
- Options I am considering: A) hire a full-time bookkeeper, B) keep the outside accountant and add bookkeeping software, C) hire someone part-time
- What matters to me in the outcome: Monthly cost, my own time freed up, accuracy of the books, flexibility if revenue drops
- Constraints (money, time, obligations, things that are not negotiable): No more than 2,500 a month in total; must be settled before year-end
- When I have to decide, and how hard it would be to undo: Decide by the end of the month; a hire is hard to undo, software can be cancelled
- Which way I am leaning, and why: Leaning toward a full-time hire because I am tired of doing the books at weekends

# Round 1 - reply with this only, then stop
1. Restate the decision in one sentence.
2. Ask up to five questions whose answers would most change the analysis. Skip anything I have already told you.
Wait for my answers. Do not start the analysis in this reply.

# Round 2 - after I answer
A. Type of decision. Say how reversible this is. If it is cheap to undo, say so and keep the rest short.
B. Options. Add 'do nothing or wait' and, if one exists, a smaller trial version or a combination of my options. Remove any option that breaks a constraint and say which constraint.
C. Criteria. List my criteria with a weight from 1 to 5, shown so I can correct them.
D. Comparison. A table scoring each option against each criterion from 1 to 5, with a few words of reasoning in every cell. Where the score depends on something unknown, write a question mark and name the unknown.
E. Failure stories. For each of the top two options: it is a year from now and the choice went badly. Give the two most plausible reasons.
F. The case against my leaning. The strongest honest argument that my current leaning is wrong.
G. Recommendation. Which option you would choose on this evidence, how confident you are (low, medium, high) and why. Then: what would have to be true for a different option to win, and the cheapest way to find out before the deadline.

# Rules
- Use only the facts I provide. Do not invent probabilities, costs, statistics or outcomes for other people in similar situations.
- Scores are structured judgment, not measurement. Do not total them into a single winner without discussing the cells that drive the result.
- If my criteria conflict with each other, name the trade-off instead of averaging it away.
- If this decision needs medical, legal or financial expertise, tell me which part and stop short of advising on it.

What a good response should contain

  • A first reply containing only a one-sentence restatement and up to five questions, for example how many hours the books take now
  • In the second reply, a note that hiring is the hard-to-reverse option and deserves more scrutiny than the software route
  • A comparison table with reasoning in each cell and question marks where the answer depends on unknown salary costs
  • A case against the full-time hire that addresses the stated motive of reclaiming weekends, and whether a cheaper option would also achieve it
  • A recommendation with a confidence level and a low-cost test, such as trialing software for a month before committing

This is an illustrative scenario showing how to fill in the prompt and what to look for. It is not a recorded model output. Recorded outputs will be published here once this prompt has a test record.

Testing and editorial review

Status: Untested. Reviewed for structure and clarity by the editorial team. No recorded model test yet.

No test record has been published for this prompt yet. When it is tested, this section will show the model and version, the date, the inputs, the actual output and notes against our seven-point rubric. We do not publish numerical scores.

Editorial record
AuthorTheBestPromptFor Editorial Team — The editorial team writes, reviews and maintains the prompts and guides on TheBestPromptFor. Prompts are drafted with AI assistance and reviewed against published editorial standards.
PublishedNovember 15, 2026
Last reviewedNovember 15, 2026
Last testedNot yet tested
Version history
  • v1.0 — November 15, 2026 · Initial version

Limitations and things to check

  • The analysis is only as complete as what you tell it. Facts you leave out, including uncomfortable ones, cannot be weighed.
  • Scores and weights are structured opinion. A different weighting can reverse the result, so check that the weights are yours.
  • The model has no stake in the outcome and no knowledge of the people involved. It cannot judge relationships, trust or your tolerance for risk.
  • For decisions that turn on medical, legal or financial questions, use the output to prepare for a conversation with a qualified professional, not to replace it.

Alternative prompts

All Productivity prompts →

Frequently asked questions

Why does the prompt ask questions instead of answering straight away?

Because the first description of a decision usually omits the facts that matter most, such as what the status quo costs or what happens if you wait. A few targeted questions improve the analysis more than extra instructions would. You can answer briefly, and 'unknown' is a valid answer.

Should I let the AI make the decision for me?

No. The recommendation is one input. The model does not bear the consequences and only knows what you typed. The more useful parts of the reply are usually the counter-argument, the unknowns in the table and the suggestion for a cheap test.

What if I do not have a leaning yet?

Write 'no leaning' in that field. The model will skip the case against your preference and you can ask it to argue against its own recommendation instead. If you notice a reaction of relief or disappointment when you read the recommendation, that tells you something too.

Sources and references

  1. Prompt engineering overview — Anthropic
  2. Prompt engineering guide — OpenAI

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