---
name: grill-me-on-this-plan
description: "Interviews you in rounds on a plan, giving a recommended answer to every question, until each branch of the decision tree is settled. Use when a plan or proposal needs a hard interview that surfaces every open decision before work starts. Do not use for brainstorming a new idea from scratch or writing the spec from settled decisions. Related topics: product, productivity."
---

# Grill Me on This Plan

Interviews you in rounds on a plan, giving a recommended answer to every question, until each branch of the decision tree is settled.

## When to use

Use this skill when a plan or proposal needs a hard interview that surfaces every open decision before work starts. Do not use it for brainstorming a new idea from scratch or writing the spec from settled decisions.

## Workflow

1. Ask the user for each input listed below in a single message, skipping any they have already given. Where options are listed, offer them, but accept other answers too.
2. Map the plan's decision tree, noting hidden assumptions and decisions that are avoided.
3. Ask the agreed number of questions per round, most consequential first, each with a recommended answer and reason.
4. Record every answer in a running decision list and let each answer open its follow-up branch.
5. Flag any answer that contradicts an earlier one and ask which stands.
6. End when no branch is open, giving the decision list and the risks accepted.

## Inputs

- **The plan** (longer free text)
- **What is at stake** (free text, e.g. "Cost of getting it wrong")
- **What is already fixed** (longer free text)
- **Tough level** (choose one: Friendly, Direct, Relentless)
- **Questions per round** (number from 3 to 8)

## Output

Rounds of numbered questions with recommended answers, then a final decision list and a list of accepted risks.

## Prompt template

Fill the inputs into this template and follow it as the full instruction.

### Grill Me on This Plan

Question me hard about this plan until every branch is decided.

- The plan: {{The plan}}
- What is at stake: {{What is at stake}}
- What is already fixed: {{What is already fixed}}
- Tough level: {{Tough level}}
- Questions per round: {{Questions per round}}

Read the plan and map its decision tree: the choices it makes, the ones it avoids and the assumptions it hides. Then run rounds. In each round ask the chosen number of questions, most consequential first, and attach your recommended answer and a one-line reason to every question so I can accept or overrule quickly. Probe the weak spots: undefined terms, missing owners, unstated dependencies, what happens on failure, and what would make us change course. Wait for my answers, record each decision in a running list, and let answers open the next branch. Where my answer contradicts an earlier one, say so. Stop when no open branch remains and give the final decision list with any risks I accepted.

## Pitfalls

- Asking easy questions first and leaving the costly decision for the last round.
- Questions with no recommendation, which makes the person do the thinking the interview was meant to save.
- Letting a vague answer stand, so the branch looks closed when it is not.