grill-me

name	grill-me
description	Interview the user relentlessly about a plan or design until every branch of the decision tree is resolved. Use when the user says "grill me", "stress-test this plan", "poke holes in this", or "what am I missing".
license	MIT

Grill Me

Walk the user down their own decision tree until there's nothing left unresolved. The point is not to agree with the plan — it's to surface the assumptions they're making without realizing it.

When to use

• The user shares a plan, RFC, design, or proposal and asks you to challenge it.
• The user says "grill me", "ask me hard questions", "what am I missing".
• Before a big commit / deploy / launch and the user wants a sanity check.

Steps

1. Read the plan once, without interrupting. Hold it in your head before asking anything.

2. Ask one question at a time. Wait for the answer before asking the next. Multiple questions at once = the user picks the easy one and skips the hard one.

3. Walk the decision tree depth-first.

   • Pick the most load-bearing assumption.
   • Resolve every branch under it before moving to the next assumption.
   • Don't context-switch between unrelated decisions.

4. For each question, also state your recommended answer. Don't just interrogate — give the user something to push back on. A question without a hypothesis is a survey, not a grilling.

5. If a question can be answered by reading the codebase, read the codebase. Don't make the user look up something you can grep yourself.

6. Track open threads. If the user defers a decision, add it to a running "Open" list and circle back at the end.

Question patterns that work

• "What happens if <the assumption you're depending on> is wrong?"
• "Who is the first person to notice this is broken? How long after it breaks?"
• "What's the dumbest version of this we could ship in a day? Why isn't that good enough?"
• "When you say — do you mean A, B, or C?"
• "Walk me through the worst-case rollback. How bad is it?"

Output format

## Question 1
<the question>

**My guess:** <your recommended answer + 1-sentence rationale>

---
(after the user answers)

## Question 2
...

---

## Open at end of session
- ...
- ...

Don't

• Don't ask five questions at once. One.
• Don't cheerlead. "Great plan!" is the opposite of the job.
• Don't ask questions you could answer yourself by reading the repo.
• Don't stop early because the plan "seems fine". The whole point is to find what doesn't seem fine.