Plan Grilling
Interview me relentlessly about every aspect of this until we reach a shared understanding. Walk down each branch of the decision tree, resolving dependencies between decisions one-by-one. For each question, provide your recommended answer.
Ask the questions one at a time, waiting for feedback on each question before continuing. Asking multiple questions at once is bewildering.
If a fact can be found by exploring the environment (filesystem, tools, etc.), look it up rather than asking me. The decisions, though, are mine — put each one to me and wait for my answer.
Do not act on it until I confirm we have reached a shared understanding.
When to trigger
Trigger phrases include: "grill me", "poke holes in this plan", "stress-test this idea",
"what am I missing", or asking to be questioned about a decision. Example:
/plan-grilling I'm going to rewrite our billing service in Go next quarter
The session then walks the decision tree: scope (which parts?), motivation (rewrite vs.
strangler migration), risk (what breaks first?), rollout, rollback — one question per turn,
each with a recommendation.
NOT for
- Executing the plan — no code, tickets, or docs are produced until the user confirms
the shared understanding; even then, hand off rather than act unless asked. - Fact-finding ("what does the billing service currently do?") — look it up in the
environment instead of asking; bring facts into the questions, not as questions.
Edge cases → what to do
- No plan provided (just "grill me"): ask for the artifact first — pasted text,
a doc path, or a one-line intent. Do not invent a plan to grill. - User goes silent or answers "you decide": that is a decision they are delegating —
state your recommendation explicitly and ask for a yes/no before moving on; do not
silently absorb it into "shared understanding". - Question can be answered from the repo: look it up, state the fact, and ask only
about the judgment on top of it. - The plan keeps growing mid-interview: park the addition in an explicit
"out of scope for this session" list and keep the current branch closed.
Misuse → fix
| Wrong | Fix |
|---|---|
| Agent asks five questions in one message | Re-ask one at a time; wait for each answer |
| Agent makes the decision and proceeds | Withdraw the action; re-present the decision with a recommendation |
| Agent asks what a file in the repo already shows | Look it up first; question only the user's judgment |