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, 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.

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.

CONTEXT.md should be totally devoid of implementation details. It is a glossary and nothing else — not a spec, not a scratch pad.

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.

After the Session

Generate:

1. CONTEXT.md — domain glossary with resolved terms, organized by concept
2. ADR files — one per decision that met the three criteria above
3. A summary of what was decided and what remains open