/grill-with-docs

name: grill-with-docs
description: "Use when a plan should be stress-tested against the project's own docs (CONTEXT.md glossary, docs/adr decisions), or the user says 'grill with docs'. Scans ADRs with adr_scanner.py and updates the docs inline as terms and decisions settle."
license: MIT
metadata:
  derived_from: "https://github.com/mattpocock/skills/tree/main/skills/engineering/grill-with-docs"
  original_author: "Matt Pocock (@mattpocock)"
  original_license: MIT
  voice: "Matt Pocock — relentless, one-at-a-time, codebase-and-docs-first, ADRs only when 3 criteria are met"
  version: 1.0.0

Grill with Docs

> Derived from [Matt Pocock's grill-with-docs](https://github.com/mattpocock/skills/tree/main/skills/engineering/grill-with-docs) (MIT, © 2026 Matt Pocock). Matt's interview discipline + docs-anchored grilling rules preserved verbatim under MIT. Additions in this repo: 3 stdlib validators (CONTEXT.md linter, ADR scanner, glossary↔code consistency check), 3 in-depth references each citing 7+ authoritative sources, `cs-grill-with-docs` agent, `/cs-grill-with-docs` command. See [Wrapper additions](#wrapper-additions) below.

<what-to-do>

Interview me relentlessly about every aspect of this plan until we reach a shared understanding. Walk down each branch of the design 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.

If a question can be answered by exploring the codebase, explore the codebase instead.

</what-to-do>

<supporting-info>

Domain awareness

During codebase exploration, also look for existing documentation:

File structure

Most repos have a single context:

/
├── CONTEXT.md
├── docs/
│   └── adr/
│       ├── 0001-event-sourced-orders.md
│       └── 0002-postgres-for-write-model.md
└── src/

If a `CONTEXT-MAP.md` exists at the root, the repo has multiple contexts. The map points to where each one lives:

/
├── CONTEXT-MAP.md
├── docs/
│   └── adr/                          ← system-wide decisions
├── src/
│   ├── ordering/
│   │   ├── CONTEXT.md
│   │   └── docs/adr/                 ← context-specific decisions
│   └── billing/
│       ├── CONTEXT.md
│       └── docs/adr/

Create files lazily — only when you have something to write. If no `CONTEXT.md` exists, create one when the first term is resolved. If no `docs/adr/` exists, create it when the first ADR is needed.

During the session

Challenge against the glossary

When the user uses a term that conflicts with the existing language in `CONTEXT.md`, call it out immediately. "Your glossary defines 'cancellation' as X, but you seem to mean Y — which is it?"

Sharpen fuzzy language

When the user uses vague or overloaded terms, propose a precise canonical term. "You're saying 'account' — do you mean the Customer or the User? Those are different things."

Discuss concrete scenarios

When domain relationships are being discussed, stress-test them with specific scenarios. Invent scenarios that probe edge cases and force the user to be precise about the boundaries between concepts.

Cross-reference with code

When the user states how something works, check whether the code agrees. If you find a contradiction, surface it: "Your code cancels entire Orders, but you just said partial cancellation is possible — which is right?"

Update CONTEXT.md inline

When a term is resolved, update `CONTEXT.md` right there. Don't batch these up — capture them as they happen. Use the format in [CONTEXT-FORMAT.md](./CONTEXT-FORMAT.md).

`CONTEXT.md` should be totally devoid of implementation details. Do not treat `CONTEXT.md` as a spec, a scratch pad, or a repository for implementation decisions. It is a glossary and nothing else.

Offer ADRs sparingly

Only offer to create an ADR when all three are true:

1. **Hard to reverse** — the cost of changing your mind later is meaningful 2. **Surprising without context** — a future reader will wonder "why did they do it this way?" 3. **The result of a real trade-off** — there were genuine alternatives and you picked one for specific reasons

If any of the three is missing, skip the ADR. Use the format in [ADR-FORMAT.md](./ADR-FORMAT.md).

</supporting-info>

Wrapper Additions

The additions below are **not** part of Matt's upstream skill. They operationalize the upstream's rules into deterministic, stdlib-only validators that pair naturally with the interview loop.

Workflow (with wrapper tools)

1. **Pre-flight (before the first question):**

• Run `scripts/context_md_linter.py CONTEXT.md` if a `CONTEXT.md` exists — confirms the glossary is well-formed before grilling against it.
• Run `scripts/adr_scanner.py docs/adr/` if `docs/adr/` exists — surfaces numbering gaps, malformed ADRs, status-frontmatter inconsistencies.
• Run `scripts/glossary_code_consistency.py --context CONTEXT.md --code src/` — flags defined-but-unused terms (dead glossary) and code-only common nouns that may need definitions. Use these flags as opening grill questions.

2. **During the session (Matt's rules apply):**

• One question per turn, walking depth-first.
• When a term is sharpened: edit `CONTEXT.md` immediately; re-run `context_md_linter.py` if the edit is structural.
• When an ADR is warranted: write it under `docs/adr/`; re-run `adr_scanner.py` to confirm numbering.

3. **Closing:**

• Final `glossary_code_consistency.py` run to confirm no new orphan terms were introduced.
• Summarize: terms added/refined, ADRs written, scenarios discussed, open items.

Tools (stdlib-only)

| Tool | One-line role | |---|---| | `scripts/context_md_linter.py` | Validate `CONTEXT.md` against the CONTEXT-FORMAT.md structure. PASS/WARN/FAIL per rule. | | `scripts/adr_scanner.py` | Walk `docs/adr/`, check `NNNN-slug.md` pattern, numbering integrity, body completeness. | | `scripts/glossary_code_consiste