grill-me

Use this when

The user asks you to grill them or stress-test a plan, decision, or idea. The aim is to uncover assumptions and resolve decisions together before acting on the result.

Start with the user's proposal and the context already available. If the subject is missing, establish what the user wants examined before asking detailed questions.

Steps

1. Map the decisions and their dependencies

Read the proposal and relevant context. Build a working decision tree: each choice connects to the further choices that depend on it. Distinguish decisions already settled by the user from open decisions and facts that still need investigation.

Identify all open decisions whose prerequisites are settled. These are the questions ready for the next round. A question that depends on another unanswered question belongs to a later round, even if both seem easy to answer.

2. Investigate facts without delaying independent questions

Look up facts available through the filesystem, tools, or other accessible evidence instead of asking the user to retrieve them. Delegate a focused fact-finding task to a subagent when a question depends on an environmental fact.

While that investigation runs, mark the fact as an unresolved prerequisite. Hold the questions that depend on it and continue with the other ready questions. When findings arrive, use them to update the decision tree; do not treat a pending investigation as a known answer.

Keep choices with the user. A fact you discovered can inform a recommendation, but it does not settle the user's decision.

3. Ask one round of ready questions

Ask every question whose prerequisites are now settled in a single round. Number each question, give it a short title, explain the choice, and provide your recommended answer. Include alternatives when they help the user understand the tradeoff.

Phrase each question so that answering "yes" accepts its recommendation. For example:

Q1 - Initial audience: Should the first version serve the internal team?

Recommended answer: Yes. Start with the internal team so its existing workflow defines the first version's scope.

Use recommendations grounded in the proposal and evidence. Separate the questions clearly so the user can answer by number. Wait for the user's answers before asking the next round; do not silently accept your own recommendations.

4. Recompute the tree after each round

Apply the user's answers, including corrections and alternatives. Update the branches they change and identify newly unblocked questions. Keep unanswered or ambiguous decisions open rather than filling them in yourself.

Incorporate completed fact-finding tasks and check which dependent decisions are now ready. Repeat the round with all currently ready questions. Continue until every branch has been examined and no decision or prerequisite remains unresolved.

If there are no ready questions but an investigation or answer is still pending, the interview is waiting, not complete.

5. Confirm the shared understanding

Review the settled tree for overlooked branches and unstated assumptions. Present the resulting understanding so the user can check that it matches their intent, and ask them to confirm it.

If they identify a gap or change a decision, reopen the affected branches and continue the rounds. Finish only when the tree has no unresolved branches and the user confirms the shared understanding. Do not implement or otherwise act on the plan before that confirmation.

Done when

• Every branch has been examined, with no unresolved decisions or silently accepted assumptions.
• Relevant facts were investigated by the agent, and no required exploration remains pending.
• Questions were asked only after their prerequisites were settled, with recommendations the user explicitly answered.
• The user confirmed that the resulting understanding matches their intent.
• No action on the plan was taken before that confirmation.