Grill With Docs

Grill With Docs

Interview the user relentlessly about every aspect of the plan until you reach shared understanding. Walk each branch of the design tree, resolving dependencies between decisions one-by-one. For each question, provide your recommended answer.

Ask questions one at a time, waiting for feedback on each before continuing. If a question can be answered by exploring the codebase, explore instead of asking.

This is the domain-aware sibling of max:grill-me. Where grill-me produces a per-dimension ambiguity report, grill-with-docs reconciles the plan with the project's documented language and decisions, and writes those docs inline as you go.

---

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).

Source & license

This open-source skill is cataloged on AgentStack and links to its original source — we do not rehost the code.

• Author: max4c
• Source: max4c/skills
• License: MIT

Install and usage instructions live in the source repository linked above.