grill-for-unknowns

name	grill-for-unknowns
description	Use when starting or reviewing a complex implementation where the user wants an agent to interrogate the plan against docs/source evidence, surface unknown unknowns, and avoid rushing into build mode. Combines docs-grounded grilling with a map-vs-territory unknowns pass.
version	0.1.1
author	Nico Bailon (co-authored by Matt Pocock)
license	MIT
metadata	{"hermes":{"tags":["planning","docs","unknowns","agentic-coding","interviews","verification"],"related_skills":["writing-plans","software-development-workflow","subagent-driven-development"]}}

Docs + Unknowns Grill

Overview

The core idea is:

• The map = the prompt, plan, assumptions, skills, prior context, docs excerpts, and the agent's current mental model.
• The territory = the real codebase, product constraints, APIs, docs, user taste, deployment environment, and failure modes.
• Unknowns = the gap between the map and the territory.

This skill combines docs-grounded grilling, one-question-at-a-time interviewing, domain modeling, and a four-quadrant unknowns pass.

The goal is not to ask endless questions. The goal is to discover the few answers that would materially change the plan (see the Material criterion below) — and to write down the shared understanding as it forms.

When to Use

Use when:

• The user says not to rush implementation, asks for a stronger plan, or wants a rigorous planning pass before orchestrating implementation work.
• The task depends on unfamiliar docs, APIs, libraries, platform behavior, or source conventions.
• The user has a vague product/design desire and likely has unknown knowns: they will know good/bad when they see it, but cannot fully specify it upfront.
• The agent is about to spawn subagents or a long-running coding agent and needs a better launch packet.
• A previous attempt failed or is stuck because the agent made assumptions, overfit to generic best practices, or missed real codebase constraints.
• Reviewing a plan/spec/PR where you need to pressure-test hidden assumptions before merge.

Do not use when:

• The task is trivial, mechanical, or already has unambiguous acceptance criteria.
• The user explicitly wants immediate execution and the risk of wrong assumptions is low.
• You can verify the right answer directly with a single tool call and no interview is needed.

Operating Mode

Stay in Explore or Plan mode until the unknowns that could change the implementation are resolved or explicitly accepted as assumptions.

Default sequence:

1. Restate the map — summarize the user's request, the intended outcome, and what is already known.
2. Read the territory — inspect the relevant docs/source/tests/config before grilling. Do not rely on vibes if docs or code are available.
3. Open a grill session ledger — use templates/grill-session.md when the session is complex enough to need a durable working doc.
4. Build the unknowns ledger — classify per the Unknowns Taxonomy below.
5. Build the domain ledger — identify fuzzy terms, overloaded concepts, vocabulary conflicts, and context boundaries. Use references/domain-modeling-add-on.md for CONTEXT.md / ADR rules.
6. Grill one decision at a time — follow the grill procedure below.
7. Propose defaults — for low-risk unknowns, choose a sensible default and label it as an assumption instead of blocking.
8. Persist shared understanding — update CONTEXT.md for crystallized domain terms and offer ADRs when the Domain Modeling criteria are met.
9. Create or revise the plan — see Implementation Plan Requirements below.
10. Ask for confirmation before build — do not enact the plan until the user confirms shared understanding, unless they explicitly authorize proceeding with labeled assumptions.
11. During implementation — keep implementation notes for deviations and newly discovered unknowns.
12. Post-implementation — produce an explainer and quiz/review checklist so the user understands what changed.

Unknowns Taxonomy

Use this table explicitly in the output when the task is ambiguous enough to justify it.

Type	Meaning	How to expose it	Example
Known knowns	Requirements already stated or proven by docs/source	Restate and cite	"Use Stripe Connect; webhook endpoint already exists."
Known unknowns	The user/agent knows a decision is unresolved	Ask targeted questions or choose labeled defaults	"Should refunds sync one-way or two-way?"
Unknown knowns	The user would recognize the right result when shown, but has not verbalized the criterion	Prototype, sketches, examples, references	"This dashboard feels too enterprise; make it more operator-like."
Unknown unknowns	Constraints or possibilities nobody has considered yet	Blindspot pass over docs/source/tests/internet; ask experts; search prior art	"The API rate limit makes this sync architecture impossible."

Docs-Grounded Grill Procedure

1. Gather evidence first

Before asking the user to decide, inspect available ground truth:

• Official docs for libraries/platforms/APIs.
• Local source files, routes, models, schemas, migrations, tests, and config.
• Existing project conventions and similar implementations.
• Error logs, CI failures, issue comments, PR diffs, or previous implementation notes.
• Reference implementations the user points to, even if in another language.

Fetch missing-but-retrievable docs; if docs cannot be accessed, say so and mark the claim as unverified.

2. Convert evidence into pressure-test questions

Good grill questions have all three properties:

• Material — the answer could change architecture, scope, UX, data model, security, permissions, or acceptance criteria.
• Grounded — the question points to docs/source behavior or a concrete uncertainty, not generic preference fishing.
• Answerable — the user can choose from options, approve a default, or supply a reference.

Bad grill questions:

• Obvious preferences that a competent agent can default.
• Exhaustive questionnaires before any research.
• Asking the user to answer things the code/docs can answer.
• Open-ended "anything else?" questions with no context.

3. Ask one material question at a time when blocked

If an answer is required to proceed, ask one question, explain why it matters, and give a recommended default. Walk the design tree branch-by-branch — do not dump the whole tree on the user at once.

Template:

Blocking question: <question>
Why it matters: <what changes if answer A vs B>
Evidence: <doc/source/test/reference citation>
Recommended answer: <default + rationale>
If you don't care: I'll proceed with <default>.

If multiple questions are useful but not blocking, keep them in the grill queue and ask the next unresolved material decision first.

Domain Modeling: Shared Language and ADRs

Grilling must also maintain shared language. During the grill, challenge fuzzy or overloaded terms immediately, compare the user's terms against existing CONTEXT.md, code identifiers, docs, and product copy, and update CONTEXT.md when a term crystallizes (glossary only — no plans, scratchpads, or ADR content).

Offer an ADR only when the decision is (1) hard to reverse, (2) surprising without context, and (3) the result of a real trade-off; otherwise record it in the session/implementation notes. See references/domain-modeling-add-on.md for file layout, formats, and examples.

Finding Unknown Unknowns: Blindspot Pass

Run a blindspot pass when the user is entering an unfamiliar domain, unfamiliar part of the codebase, or high-stakes integration: search the relevant docs/source/tests for unknown unknowns that could materially change the plan, explain them in plain language, rank by implementation risk, and suggest how to resolve each one cheaply.

Output shape:

## Blindspot Pass

### Highest-risk unknown unknowns
1. <unknown>
   - Why it matters:
   - Evidence:
   - Cheap resolution:
   - Decision owner: user / agent / docs / prototype

### Likely safe assumptions
- <assumption> — why safe, how to verify later

### Questions worth asking now
1. <one material question>

Unknown Knowns: Brainstorms, Prototypes, and References

When the user will recognize the right answer visually or behaviorally but cannot fully specify it:

• Build cheap prototypes before wiring real systems — e.g., a single-file mock with fake data showing 3 distinct directions.
• Offer multiple directions with meaningful contrast, not tiny variations.
• Ask the user to react to examples, screenshots, demos, or reference source — e.g., 2-3 similar in-repo modules plus one external reference, then ask which behavior to match.
• Capture the user's reactions as explicit criteria.

Implementation Plan Requirements

When producing the plan, lead with the decisions most likely to change:

1. Decision surface — data model, type interfaces, permissions, user-facing flows, API semantics, migration strategy.
2. Evidence — docs/source references that justify the plan.
3. Open questions — only material unknowns, ranked by risk.
4. Resolved assumptions — low-risk defaults the agent will use unless corrected.
5. Prototype/reference artifacts — links or paths if relevant.
6. Implementation steps — bite-sized, ordered, with verification gates.
7. Deviation policy — what the implementer should do if the territory contradicts the map.

During Implementation: Notes and Deviations

For complex work, create a temporary implementation notes file such as implementation-notes.md or include an equivalent section in the final report. Use templates/implementation-notes.md for the minimum sections: plan snapshot, decisions made, deviations, new unknowns, and verification.

Default deviation policy:

• If the issue is low-risk and local, choose the conservative option, log it, and continue.
• If the issue changes architecture, data migration, security, cost, or user-facing behavior, stop and ask.
• If docs contradict the plan, trust the docs/source over the original map and update the plan.

Post-Implementation: Explain, Pitch, Quiz

After implementation, help the user and reviewers understand the territory discovered during the work.

Deliver:

• What changed and why.
• Which unknowns were resolved.
• Which assumptions remain.
• Docs/source evidence for important behavior.
• Verification results from real commands/tests.
• A short quiz/checklist if the user needs to understand before merge — every quiz item must be answerable from the report itself.

Subagent / Coding-Agent Launch Packet

Before spawning a subagent or external coding agent, prepare a launch packet from templates/launch-packet.md. It covers: goal, map, territory to inspect first, the four unknowns categories, deviation policy, and verification gates.

If using multiple subagents, split roles:

• Docs scout — reads official docs/source and returns constraints.
• Codebase scout — maps existing patterns and tests.
• Prototype scout — creates cheap visual/API alternatives to expose unknown knowns.
• Implementer — edits only after the plan is stable enough.
• Reviewer — grills the diff against the launch packet and docs.

Calibration: Over- vs Under-Constraining

• Too specific, and the agent follows instructions even when a pivot is better. Define the goal, constraints, and stop/continue rules; leave room for implementation judgment.
• Too vague, and the agent defaults to generic best practices that may not fit the product/codebase. Provide references, docs, taste examples, and acceptance criteria.

Verification Checklist

Before moving from planning to implementation:

• Relevant docs/source/tests/config were inspected, or the lack of access is stated.
• Known knowns, known unknowns, unknown knowns, and suspected unknown unknowns are listed.
• Blocking questions are material and include recommended defaults.
• Low-risk unknowns are converted into labeled assumptions rather than blocking progress.
• The plan leads with likely-to-change decisions, not mechanical steps.
• Deviation policy is explicit for long-running/subagent work.
• Verification gates are defined before implementation begins.

Before finalizing implementation:

• Deviations and newly discovered unknowns were logged.
• Tests/checks/manual verification were actually run and reported.
• Remaining assumptions are visible.
• The user/reviewer gets an explainer sufficient to understand the change.

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Adapted from Matt Pocock's grilling + domain-modeling skills and Thariq's "Finding Your Unknowns" article — see README.md for full attribution.