docs: rewrite the grill-me page around what people get wrong

The old page explained the mechanism and stopped. It answered none of
the questions people actually ask: which grilling skill to reach for,
how many questions is normal, what to do with a question talking can't
settle, whether to clear context before to-spec.

Keep the mechanism short and spend the page on judgement instead:
three-way sibling routing keyed on what you have in front of you; a
section naming passivity as the main failure mode; grillable vs
ungrillable as the move for questions that need a prototype; an
"It's working if" list; and a "Common questions" section answering the
six highest-volume ones. Say plainly to leave plan mode off.

Sourced from user questions across X, Discord and YouTube.

.changeset/docs-grill-me-pass.md

@@ -0,0 +1,17 @@
+---
+"mattpocock-skills": patch
+---
+
+Rewrite the `grill-me` docs page around what people actually get wrong.
+
+The old page explained the mechanism — rounds, the frontier, the decision tree — and stopped there. Every recurring question from the last few months went unanswered on it: which of the three grilling skills to reach for, how many questions is normal, what to do when a question can't be answered by talking, and whether to start a fresh session before writing the spec.
+
+The rewrite keeps the mechanism short and spends the page on the judgement calls instead:
+
+- **Sibling routing** is now a three-way list keyed on what you have in front of you — no codebase, a codebase, or too big for one session — rather than a paragraph.
+- **"It's a conversation, not an interview"** names passivity as the main failure mode. A session where you answer "agreed" forty times produces a plan you didn't write and can't defend.
+- **"Grillable and ungrillable"** gives readers the move for a question that talking cannot settle: stop, prototype, come back. This is where long sessions come from.
+- **A "Common questions" section** answers the six highest-volume ones directly, including how to restore one-question-at-a-time and why you should not clear context before `to-spec`.
+- **"It's working if"** added, led by the sharpest signal: if you never disagreed, you didn't need the session.
+
+Also drops the "plan mode" ambiguity by saying plainly to leave it off.

docs/productivity/grill-me.md

@@ -2,22 +2,71 @@
 
 ## What it does
 
-`grill-me` runs a relentless interview about a plan or design, walking every branch of the decision tree until you and the agent reach a **shared understanding**.
+`grill-me` interviews you about a plan until every decision inside it has been made on purpose rather than by default. It asks in **rounds**: each round is the whole **frontier** — every question whose prerequisites you have already settled — so you are never asked something that hinges on an answer it hasn't heard yet.
 
-It asks in **rounds** and waits. A round is the whole **frontier** — every decision whose prerequisites are already settled — put to you as one numbered list, so you're never asked something that hinges on an answer the agent hasn't heard yet. Where a question can be answered by reading the codebase, it goes and reads rather than asking. Each question comes with the agent's own recommended answer, so you are reacting to a proposal, not staring at a blank prompt.
+It is **stateless**. It writes no files and leaves no workspace behind. The only thing it produces is a sharper plan in your own head.
 
 ## When to reach for it
 
-You invoke this by typing `/grill-me` — the agent won't reach for it on its own.
+You invoke this by typing `/grill-me` — the agent won't reach for it on its own. Start it in a **fresh conversation**, not on top of a plan you already had an agent write.
 
-Reach for it before you build, when a plan feels roughly right but you can sense unresolved decisions hiding in it — the moment you want the soft spots found and forced into the open. If you want that same interrogation to also leave a paper trail of ADRs and a glossary behind, use [grill-with-docs](https://aihero.dev/skills-grill-with-docs) instead. And if the effort is too big to hold in one session and the route to the goal is still foggy — a greenfield project, a huge feature build — start further upstream with [wayfinder](https://aihero.dev/skills-wayfinder), which charts it as a map of decisions first and then merges back into this flow.
+Reach for it when a plan feels roughly right and you suspect it isn't. Which of the three grilling skills you want depends on what is in front of you:
 
-## The decision tree
+- **No codebase yet** — `grill-me`. There is nothing to align against, so there is nothing worth recording.
+- **A codebase** — [grill-with-docs](https://aihero.dev/skills-grill-with-docs). The same interview, but stateful: it keeps what it learns in `CONTEXT.md` and ADRs.
+- **Too big for one session** — [wayfinder](https://aihero.dev/skills-wayfinder). It charts the effort as a map and runs grilling sessions inside it.
 
-The session walks the plan as a tree of decisions, settling a parent decision before the choices that hang off it. Your answers reshape the tree and push the frontier outward, so the next round asks whatever they unblocked. The point is not to reach agreement quickly; it is to make every implicit call explicit, so nothing important is left silently assumed. You come out the other side with a plan whose branches have all been visited.
+Leave plan mode off. Plan mode primes the agent to rush toward producing a plan, which is the opposite of staying in inquiry.
 
-`grill-me` is **stateless**: it writes nothing and leaves no workspace behind. It runs anywhere, and the only artifact is the sharpened understanding in the conversation itself. That is the deliberate contrast with [grill-with-docs](https://aihero.dev/skills-grill-with-docs), which captures the same interview as durable ADRs and a glossary.
+## It's a conversation, not an interview
+
+The skill asks the questions, but **you** own the scope. That is the part people miss, and it separates a session that sharpens a plan from one that produces confident nonsense.
+
+The failure mode is **passivity** — answering "agreed, agreed, agreed" for forty questions and coming out with a plan the agent wrote and you nodded at. It feels productive because it was long. Nothing was actually decided, and the result carries a certainty it hasn't earned.
+
+Being active means steering. Push back on a question pitched beneath the fidelity you need. Say when the scope is drifting. Answer "I don't know" and mean it. This skill is built to aid an engineer, not to replace one: what comes out tracks the quality of your answers, not the number of questions asked.
+
+The opposite error is real but rarer — staying in the interview so long you never reach code.
+
+## Grillable and ungrillable
+
+Some questions can be answered by talking. Others can't, and no amount of grilling will get you there.
+
+"One long form or three pages?" and "how should this interaction feel?" are **ungrillable** — they need something to react to. When you hit one, stop grilling. Build the throwaway version with [prototype](https://aihero.dev/skills-prototype), look at it, then come back and answer in one line.
+
+Talking your way through an ungrillable question is where sessions balloon. The agent keeps rephrasing, you keep guessing, and the scope grows to fill the uncertainty.
+
+## It's working if
+
+- You disagree with something. A session with no pushback from you is a session you didn't need.
+- Questions arrive in a few rounds rather than one long drip, and later rounds clearly build on what you said earlier.
+- You end up somewhere you didn't expect, because a question surfaced a decision you had been making implicitly.
+- At the end you could defend each choice to someone who wasn't there.
+
+## Common questions
+
+**How many questions should I expect, and how do I know when it ends?**
+Count rounds, not questions. Forty-six questions across four rounds is an ordinary session. It ends when the frontier is empty — every branch visited, nothing left silently assumed.
+
+**It asked me two hundred questions. What went wrong?**
+Usually the scope was too large. Ask the agent to break the work into smaller pieces first, then grill each one. Very long sessions also drift into the **dumb zone**, where the context window is full enough that the questions get worse.
+
+**Can I go back to one question at a time?**
+Yes. Add this to your global `CLAUDE.md`:
+
+```
+When grilling, ask one question at a time.
+```
+
+**What if I genuinely don't know the answer?**
+Say so. "I don't know" is a real answer, and a question you can't answer is usually a sign to prototype rather than to guess.
+
+**Do I start a fresh session before writing the spec?**
+No. The value of the session is the context you just built. Hand the same conversation straight to [to-spec](https://aihero.dev/skills-to-spec).
+
+**Does the model matter?**
+More than for most skills. Grilling leans on the model's own sense of how systems break, so give it your best one. Implementation mostly follows context and tolerates a cheaper model.
 
 ## Where it fits
 
-`grill-me` is a reach-for-it-anytime standalone — the pre-build stress test you run whenever a plan needs hardening. It is the stateless, user-invoked front door to the [grilling](https://aihero.dev/skills-grilling) primitive; its closest neighbour is [grill-with-docs](https://aihero.dev/skills-grill-with-docs), the stateful sibling that runs the same interview but additionally records the decisions as ADRs and a glossary. If the outcome is a spec you want written down, hand off to [to-spec](https://aihero.dev/skills-to-spec), which synthesises the settled understanding into a spec without re-interviewing you. When you're unsure which flow fits, [ask-matt](https://aihero.dev/skills-ask-matt) routes you.
+`grill-me` is a reach-for-it-anytime standalone — the pre-build stress test you run whenever a plan needs hardening. It is the stateless, user-invoked front door to the [grilling](https://aihero.dev/skills-grilling) primitive; its closest neighbour is [grill-with-docs](https://aihero.dev/skills-grill-with-docs), the stateful sibling that runs the same interview against a codebase and records the decisions as ADRs and a glossary. When the plan is settled, hand the conversation to [to-spec](https://aihero.dev/skills-to-spec), which writes it up without re-interviewing you. When you're unsure which flow fits, [ask-matt](https://aihero.dev/skills-ask-matt) routes you.