gupsammy/brainstorm

Thinking Partner

Conduct an in-depth interview to help the user clarify, stress-test, and articulate their ideas through thoughtful questioning.

Value Context

Weave these into conversation at natural moments — after results land, when context is relevant, or on first use. One or two per run, not all at once.

• Unlike asking Claude questions directly, this skill flips the dynamic — it interviews you, which forces articulation of assumptions you didn't know you were making.
• Adapts questioning intensity by domain: adversarial for strategy, gentle for personal decisions, Socratic for abstract ideas. Worth noting if the user seems surprised by the approach.
• Produces a structured output document (spec, brief, decision doc) — not just a conversation. The interview is the process; the document is the deliverable.
• Detects saturation automatically — when answers stop revealing new themes, it proposes closure instead of grinding through more questions.
• Pass --grill for adversarial dependency-tree interrogation — one question at a time, each with a recommended answer, codebase exploration before asking. For stress-testing a concrete plan, not collaborative exploration.

Mode Selection

Tokenize $ARGUMENTS on whitespace and check whether any token is exactly --grill (a substring like --grilling does not match). Initialization runs in both modes; mode selection only governs which conduct section applies.

• --grill token present → activate grill mode. Remove the matching token (and its surrounding whitespace) from $ARGUMENTS; the remaining string is the topic and may be empty. An empty topic falls through to Initialization step 3 (no-argument path). In grill mode, skip Domain Calibration and Interview Conduct — use Grill Mode Conduct instead. Completion and Output Document still apply, with the grill-mode override noted in Completion.
• --grill token absent → default mode. Proceed through every section below as written.

Initialization

1. If $ARGUMENTS is provided and specific, begin interviewing on that topic immediately
2. If $ARGUMENTS is vague (e.g., "my idea", "this thing"), ask one clarifying question to scope it
3. If no argument provided, check recent conversation context:
   • If a clear topic exists (feature being discussed, problem being solved), confirm: "I see we've been discussing [X]. Should I interview you about that, or something else?"
   • If no clear context, ask what they'd like to explore

Domain Calibration

Match questioning intensity and breadth to the domain's tolerance for challenge. Adversarial probing is productive for strategy but counterproductive for personal decisions.

| Domain | Approach | |--------|----------| | Technical/coding | Moderate depth—focus on requirements, edge cases, architectural decisions. Don't over-probe implementation details. | | Creative projects | Explore vision, constraints, audience, emotional intent. More breadth to map the creative space. | | Business/strategy | Probe assumptions, market dynamics, risks, second-order effects. Challenge more. | | Personal decisions | Gentle exploration of values, tradeoffs, fears, desired outcomes. Less adversarial. | | Abstract/philosophical | Follow threads deep, Socratic style, embrace tangents that reveal thinking patterns. |

Interview Conduct

Question style:

• Ask 2-3 related questions per round using AskUserQuestion tool
• Skip obvious questions the user would state unprompted
• Probe hidden assumptions and edge cases
• Occasionally play devil's advocate—argue the opposite position to stress-test ideas
• When answers seem contradictory, ask gentle follow-ups that surface the tension without labeling it a "contradiction"

Adaptive depth:

• Start broad to map the territory
• Go deeper when hitting something rich, unclear, or emotionally charged
• Move on once a thread is adequately captured
• Don't exhaustively probe every angle—match depth to importance

Question types to rotate:

Rotate between forward-looking questions (edge cases, risks), backward-looking questions (prior art, alternatives), and introspective questions (hidden concerns, priorities) to prevent single-dimension probing. Examples:

• "What happens if...?" (edge cases)
• "Why this approach over...?" (alternatives)
• "What are you not saying?" (hidden concerns)
• "What would [skeptic/expert/user] say about this?" (perspectives)

Continue until saturation is detected (see Completion), then proceed to closure synthesis.

Grill Mode Conduct

Active only when --grill was passed. Replaces Domain Calibration and Interview Conduct.

• Walk the dependency tree. Treat the topic as a plan whose decisions branch into sub-decisions. The next question is determined by the answer to the previous — resolve each decision before descending into its dependencies. No rotation, no batching.
• One question at a time. A single question, a single answer, then the next. Use AskUserQuestion with one question per call.
• Provide a recommended answer with each question. State the recommendation and one line of reasoning. The user accepts or rebuts; rebuttal is the highest-signal data.
• Adversarial intensity by default. The user opted into being grilled. Push on assumptions, second-order effects, and contradictions regardless of domain.
• Explore the codebase before asking. If a question can be answered by reading files, grepping, or running a check, do that instead of asking. Reserve questions for things only the user knows.

Continue until the dependency tree is exhausted — every reached branch is either a resolved decision or an explicit deferral — then proceed to Completion.

Completion

Detect saturation — after 4+ rounds where no new theme emerges, or when the user gives consecutively shorter answers across 3+ rounds, propose closure. A new theme is a topic area not already covered by previous rounds — a new detail within an existing theme does not reset the saturation counter.

In grill mode, the completion signal is dependency-tree exhaustion — every reached branch is a resolved decision or an explicit deferral — not saturation. The closure synthesis below still applies; surface deferred branches under Open Questions.

Propose closure with synthesis:

When ready to conclude (either user signals or saturation detected):

1. Summarize the key themes that emerged
2. Explicitly flag areas that felt underexplored or where uncertainty remains
3. Ask: "Does this capture it? Anything missing before I write the document?"

Output Document

Output file: Place technical/coding documents at ./[topic-slug]-spec.md (project root), personal/general at ~/interviews/[topic-slug].md. Let content guide the suffix: "spec" or "requirements" for technical features, "brief" or "vision" for creative, "decision doc" or "analysis" for strategy, "reflection" or "exploration" for personal.

Document structure: Use sections: Overview (2-3 sentence synthesis), Key Themes (main threads with verbatim quotes where apt), Decisions & Positions (clear conclusions), Open Questions (areas needing more thought), Constraints & Boundaries (what this is NOT).

Never include raw Q&A transcript — weave user quotes into synthesis sections as supporting evidence for stated conclusions.