
Plan Interrogator
Stress-test any plan in max 3 bounded rounds — exit with a build-ready spec, not an endless interview.
v1.0.0 · ~839 tokens · ⬇ 0 · Updated July 6, 2026
What it does
Grill-style plan review with hard bounds: max 3 rounds x 5 questions, every question must name what it blocks, and the interrogation exits the moment a 6-point completeness gate passes. Ships a structured SPEC block (goal, scope, data, edge cases, failure policy, acceptance checks) the implementer can follow without guessing. Where existing grill skills loop until fatigue, this one is engineered to stop.
Example uses
Grill a feature plan
You have a feature sketched out and want the holes found before any code exists, not during code review.
Here's my plan: add CSV import to our CRM so sales can bulk-upload leads — parse the file, dedupe against existing contacts by email, assign owners round-robin. Interrogate it: undefined behaviors, exact data shapes, failure modes. Max three rounds, then hand me the build-ready spec.Spec out a vague request
A stakeholder request is one sentence long and the implementer would otherwise be guessing at every decision.
Product asked for 'notifications when an order is delayed'. Before we build anything, interrogate this: which delays count, who gets notified through which channel, and what happens on repeated delays for the same order. Where I answer 'you decide', make the call and record it in the spec under decisions made for me.Pressure-test a migration plan
You are planning a risky change like a data migration and want the failure modes enumerated before the weekend it happens.
We plan to migrate user sessions from Redis to Postgres over one weekend. Stress-test the plan: the rollback story, what happens to sessions that are live mid-migration, and whether we dual-write or hard-cutover. Exit with a spec that includes acceptance checks I can hand to the team.Install
# 1. Create the skill folder in your Claude setup mkdir -p ~/.claude/skills/plan-interrogator # 2. Download SKILL.md into it (or move the file you just downloaded) # → ~/.claude/skills/plan-interrogator/SKILL.md # 3. Claude Code auto-discovers it on next launch.
Inside the skill
---
name: plan-interrogator
description: Stress-test a plan or spec BEFORE any code is written. Use when the user shares a plan, feature idea, or spec and wants it challenged ("grill my plan", "poke holes", "review this spec"), or before implementing any non-trivial feature. Runs a BOUNDED interrogation (max 3 rounds) and exits with a build-ready spec.
---
# Plan Interrogator
Interrogate a plan until it is safe to build — then STOP. The output is a spec the
implementer can follow without guessing. This is not conversation; every question
must change what gets built.
## Hard bounds (non-negotiable)
- **Max 3 rounds** of questions, **max 5 questions per round**.
- Never ask something the plan (or an earlier answer) already covers.
- Every question must name **what it blocks**: "Blocks: error handling in the import loop."
- If the user answers "you decide", make the call, record it in the spec under
**Decisions made for you**, and move on. Do not re-ask.
- Exit EARLY the moment the completeness gate passes. Fewer questions is better.
## Question priority (spend your budget in this order)
1. **Undefined behavior** — inputs, states, or user actions the plan never mentions.
"What happens when X is empty / duplicated / mid-flight?"
2. **Data shape and ownership** — exact fields, types, who writes, who reads,
what is the source of truth when two things disagree.
3. **Failure modes** — what may fail (network, validation, permissions), what the
user sees, whether the operation retries, rolls back, or half-completes.
4. **Scope boundary** — what is explicitly OUT. Unstated scope is how projects rot.
5. **Verification** — how a reviewer will confirm it works. If it cannot be
verified, it is not a requirement; rewrite or cut it.
Skip any category the plan already answers. Do not invent hypotheticals with no
implementation impact ("what if the user has 10 million rows" on an internal tool
with 40 rows) — that is interrogation theater.
## Completeness gate (exit when ALL are true)
- [ ] Happy path is unambiguous end-to-end (no "somehow", "etc.", "and so on").
- [ ] Edge cases are enumerated, each with its expected behavior.
- [ ] Data shapes are concrete (fields + types), including what is optional.
- [ ] Failure policy is stated (fail loud vs degrade, retry vs abort, rollback).
- [ ] Out-of-scope list exists and the user has seen it.
- [ ] At least 3 acceptance checks are listed, each testable in one sentence.
## Output format (always end with this block)
```
SPEC — <feature name> — v1
Goal: <one sentence>
In scope: <bullets>
Out of scope: <bullets — explicit>
Data: <shapes, ownership, source of truth>
Edge cases: <case → expected behavior>
Failure policy: <what fails how, user-visible behavior>
Acceptance checks: <3+ verifiable one-liners>
Decisions made for you: <calls made on "you decide" answers>
Open risks: <anything accepted-but-unresolved, or "none">
```
## Anti-patterns (refuse these behaviors)
- Asking questions whose answer changes nothing in the code.
- A 4th round. If the gate still fails after 3 rounds, ship the spec with the
gaps listed under **Open risks** and say so plainly.
- Padding the spec with sections the project does not need.
- Swallowing disagreement: if an answer contradicts an earlier one, surface the
conflict immediately — do not silently pick one.
Changelog
- v1.0.02026-07-03Initial clean-room write.
Frequently asked questions
Is Plan Interrogator free?
Yes. Plan Interrogator is free to download and MIT-licensed.
Where do I install Plan Interrogator?
Place the SKILL.md file in ~/.claude/skills/plan-interrogator/ and Claude Code auto-discovers it on next launch.
How many tokens does Plan Interrogator use?
About 839 tokens — it is designed to be token-lean.

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