Grill with docs

Use this skill to stress-test a plan or design through relentless interrogation while simultaneously maintaining the project's domain glossary (CONTEXT.md) and capturing architectural decisions (ADRs) as they crystallise.

Use this skill when

• The user wants to be grilled or stress-tested on a plan that touches domain concepts.
• Domain terminology in the project is fuzzy, inconsistent, or undocumented.
• The user explicitly says "grill me" and mentions domain docs, CONTEXT.md, or ADRs.
• A plan exists but the shared understanding between user and agent is not yet solid, and domain language should be captured along the way.
• The user wants to build or update CONTEXT.md as part of planning.

Do not use this skill when

• The user wants pure interrogation without any documentation side-effects — route to grill-me.
• The request is under-specified and needs sharpening before it can be interrogated — route to reverse-prompt.
• A completed /plan needs formal review by Jason/Freddy personas — route to plan-review-loop.
• The user wants to write standalone documentation (README, guide, runbook) — route to doc-coauthoring.
• The user wants a pre-edit file/test map — route to context-map.

Routing boundary

Situation	Use this skill?	Route instead
User says "grill me on this plan" and the plan touches domain concepts	Yes	-
User wants domain glossary built from scratch during planning	Yes	-
User wants pure interrogation, no doc maintenance	No	grill-me
User's request is too vague to interrogate	No	reverse-prompt
Completed /plan needs formal approval-gate review	No	plan-review-loop
User wants a standalone document authored collaboratively	No	doc-coauthoring
User needs to map files and tests before editing	No	context-map

Inputs to gather

Required before starting

• The plan, design, or feature the user wants stress-tested.
• The repository root where CONTEXT.md and docs/adr/ should live.

Helpful if present

• An existing CONTEXT.md or CONTEXT-MAP.md in the repository.
• An existing docs/adr/ directory with prior decisions.
• Prior conversation context about the feature being planned.

Only investigate if encountered

• Code that contradicts what the user says about how things work.
• Multiple bounded contexts in a monorepo (signalled by CONTEXT-MAP.md).

First move

1. Check whether CONTEXT.md (or CONTEXT-MAP.md) and docs/adr/ exist in the repository.
2. If CONTEXT.md exists, read it. If ADRs exist, scan them for decisions relevant to the plan.
3. Begin the interrogation: ask the first question about the plan, providing your recommended answer using the ask_user tool.

Workflow

1. Interrogate one question at a time. Walk down each branch of the design tree, resolving dependencies between decisions sequentially. For each question, provide your recommended answer. Wait for the user's response before continuing.

2. Explore before asking. If a question can be answered by exploring the codebase, explore the codebase instead of asking the user.

3. 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?"

4. 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?"

5. Discuss concrete scenarios. Stress-test domain relationships with specific scenarios that probe edge cases and force precision about boundaries between concepts. See references/session-playbook.md for patterns.

6. Cross-reference with code. When the user states how something works, verify against the code. If you find a contradiction, surface it: "Your code cancels entire Orders, but you just said partial cancellation is possible — which is right?"

7. Update CONTEXT.md inline. When a term is resolved, update CONTEXT.md immediately — do not batch. Use the format in references/context-format.md. Create CONTEXT.md lazily if it does not exist yet. Do not couple CONTEXT.md to implementation details; only include terms meaningful to domain experts.

8. Offer ADRs sparingly. Only offer to create an ADR when all three conditions are met: (a) hard to reverse, (b) surprising without context, (c) the result of a real trade-off. If any condition is missing, skip the ADR. Use the format in references/adr-format.md. ADRs live in docs/adr/ with sequential numbering. Create the directory lazily if it does not exist yet.

Outputs

• Updated or newly created CONTEXT.md with resolved domain terms.
• Zero or more ADRs in docs/adr/ for qualifying decisions.
• A shared understanding of the plan, documented through the glossary and decision records.

Guardrails

• Ask questions one at a time. Never dump a wall of questions.
• Provide your recommended answer with every question.
• Update CONTEXT.md inline as terms resolve. Do not batch documentation updates to the end.
• Do not add general programming concepts to CONTEXT.md — only project-specific domain terms.
• Do not offer an ADR unless all three conditions (hard to reverse, surprising, real trade-off) are met.
• Do not create CONTEXT.md or docs/adr/ until you have something to write in them.
• Keep CONTEXT.md definitions to one sentence. Define what a term IS, not what it does.

Validation

• Confirm that every term added to CONTEXT.md follows the format in references/context-format.md.
• Confirm that every ADR created follows the format in references/adr-format.md and meets all three offering criteria.
• Confirm that CONTEXT.md does not include implementation-specific terms.
• Run node skills/skill-authoring/scripts/validate-skill-library.mjs skills/grill-with-docs/SKILL.md.
• Smoke test:
  • should trigger: "Grill me on this plan to add order cancellation — I want the domain language documented."
  • should not trigger: "Sharpen this vague request into a proper brief before I start." (→ reverse-prompt)

Examples

• "Grill me on this plan to refactor the notification system — build up CONTEXT.md as we go."
• "Stress-test my design for the new auth flow against the existing domain model in CONTEXT.md."
• "I need to work through the payment processing changes — interrogate me and capture any ADRs along the way."

Reference files

• references/context-format.md — CONTEXT.md format specification: structure, rules, single vs. multi-context repos
• references/adr-format.md — ADR format, offering criteria, qualifying categories, and optional sections
• references/session-playbook.md — interrogation patterns: scenario construction, contradiction surfacing, fuzzy-term resolution
• assets/context-template.md — starter template for a new CONTEXT.md