# Grill With Docs

> Grilling session that challenges your plan against the existing domain model, sharpens terminology, and updates documentation (CONTEXT.md, ADRs) inline as decisions crystallise. USE FOR: stress-testing plans against project language, building shared vocabulary, documenting decisions, domain-driven design sessions. DO NOT USE FOR: non-code grilling (use grill-me), writing code, debugging.

- Skill: `habonn/grill-with-docs` (Agent Skill)
- Install (CLI): `npx skillmds@latest add habonn/grill-with-docs`
- Raw SKILL.md: https://api.skillmd.com/api/skills/habonn/grill-with-docs/raw
- Safety review: pending
- Works with: Claude Code, Claude.ai, OpenAI Codex
- Category: AI & ML
- Author: habonn (https://skillmd.com/u/habonn)
- Updated: 2026-09-17
- Page: https://skillmd.com/skills/habonn/grill-with-docs

---


# Grill With Docs

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.

## 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.

Don't couple `CONTEXT.md` to implementation details. Only include terms that are
meaningful to domain experts.

### 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.