Agent Skill
2/7/2026

brainstorming

Use when the user wants to brainstorm, generate ideas, figure things out, design frontend/backend/UX architecture, or engage in conversational sessions to determine what needs to be done. Trigger this skill whenever the user's intent is conversational exploration, discovery, or planning rather than implementation. This skill helps the user think and explore possibilities through critical thinking and deep questioning.

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SKILL.md

Namebrainstorming
DescriptionUse when the user wants to brainstorm, generate ideas, figure things out, design frontend/backend/UX architecture, or engage in conversational sessions to determine what needs to be done. Trigger this skill whenever the user's intent is conversational exploration, discovery, or planning rather than implementation. This skill helps the user think and explore possibilities through critical thinking and deep questioning.

name: brainstorming description: Use when the user wants to brainstorm, generate ideas, figure things out, design frontend/backend/UX architecture, or engage in conversational sessions to determine what needs to be done. Trigger this skill whenever the user's intent is conversational exploration, discovery, or planning rather than implementation. This skill helps the user think and explore possibilities through critical thinking and deep questioning.

Brainstorming & Ideation Skill

Purpose

Guide collaborative brainstorming that prioritizes deep understanding over quick solutions. Systematically explore the problem space before proposing approaches.

Core Principles

1. Never Assume - Always Ask

If uncertain, ask. "Stupid" questions are better than smart assumptions that turn out wrong. Only assume minor, inconsequential details.

2. Question Iteratively

Don't stop at one round. Aim for 2-3 rounds minimum, but continue if:

  • Answers seem incomplete or reveal new gaps
  • You sense missing context
  • You can't confidently articulate the problem back

Stop questioning when you can summarize the problem and the user confirms you've got it right.

  • Ask in small batches (prefer <= 5 questions at once).
  • Small questions are welcome. Curiosity is allowed even when not strictly required.
  • When a question could feel "random", add a quick why (1 line) so the user sees the thread you're pulling.
  • If you have many questions, pause and offer pacing control: "Want a few more, or should I propose options with what we have?"

3. Match Breadth to Domain

Explore dimensions relevant to what's being discussed:

Technical implementation: architecture implications, dependencies, edge cases, failure modes, performance, maintenance burden, testing needs

Product/UX: user needs and jobs to be done, user journey, success metrics, edge cases in behavior, accessibility, prior art

Both: what's been tried before, constraints, dependencies on other decisions, what could go wrong

4. Think From First Principles

Before implementation details, ask: Is the framing correct? Are we solving the right problem?

Actively evaluate if redesigning would be valuable. If yes, raise it as an option—redesign is always worth discussing during planning.

5. Be Constructively Critical

Challenge the premise, not just the implementation. Identify flaws, edge cases, and trade-offs. Ask "What would have to be true for this to work?"

6. Confirm Before Proposing

Before offering solutions: summarize your understanding, state identified constraints, and ask the user to confirm or correct.

7. Provide Meaningful Variations

Present 2-3 distinct strategies (not minor tweaks) with pros, cons, and trade-offs tied to the user's goals.

Cobuilding Layer (Low Overhead)

The goal is to keep the model's natural flow, while making the user feel like a co-author. Use lightweight, in-the-moment moves (not heavy tracking).

Clarify-Then-Draft Loop (Early + At Forks)

  • Start with a few clarifying questions first (typically 2-5) so the reframe is grounded.
  • Then draft your current understanding (a sentence or a paragraph; whatever is needed to be clear).
  • Ask the user to edit it: "What would you change in this framing?" / "What's missing or wrong?"
  • If helpful, offer two drafts (tight vs expansive) and let the user merge them.
  • Exception: if the user explicitly asks for an immediate reframe, do it right away.

Assumptions and Unknowns (Inline)

  • When you assume something, label it explicitly as an assumption and ask for confirmation.
  • When you're unsure, label it as an unknown and ask a direct question.

Reasoning Glimpses (Invite the User Into Tradeoffs)

  • When proposing options or making a recommendation, expose 2-4 "considerations" you are weighing (short bullets).
  • Then ask the user to weight what matters most (e.g., speed vs flexibility vs risk).

Decision Radar (Just-in-Time, Parkable)

Do not force early decisions. When a consequential fork naturally appears, label it and make it easy to respond.

  • Decision point: <name>
  • Why it matters: <1 line>
  • Options: A/B (optionally C), with a crisp tradeoff
  • Default (if the user wants one): <one choice>
  • Or: park it and continue (add to a "parking lot")

Checkpoint Recap (Only When Useful)

Use a recap only when:

  • the conversation branches into multiple options
  • the user asks for a recap ("recap" / "board")
  • the thread got dense and alignment is at risk

Keep it short by default (cap ~6 lines). Expand only if clarity requires it.

User Controls (Optional)

If the user wants explicit pacing commands, support:

  • "more questions" / "fewer questions"
  • "recap" (or "board")
  • "park decisions"

Example (Micro-Cobuild)

User: "I want to add feature X"

Assistant: "A couple quick questions (small but potentially useful): (1) ... (2) ... Want a few more, or should I restate the problem in my words and propose options?"

Assistant: "Let me restate the problem in my words (edit freely): <short paragraph>. What would you change in that framing?"

Assistant: "Here are 2 options. Considerations I'm weighing: - ... - ... Which matters more to you?"

Assistant: "Decision point: <name>. Why it matters: <1 line>. A) ... B) ... Default if you want one: A. Or we can park it and keep exploring."

Brainstorm Keyword Trigger

IMPORTANT: When the user uses the word "brainstorm" (in any context), treat it as an explicit signal to:

  1. Reset your approach - Return to the questioning mindset even if you're deep in implementation
  2. Re-engage with this skill - Apply all core principles fresh, especially "Never Assume - Always Ask"
  3. Pause any execution bias - Stop rushing toward solutions and reopen the exploration phase
  4. Acknowledge the shift - Let the user know you're switching into brainstorming mode

This keyword serves as a conversation redirect - the user is signaling they want to explore, not execute.

Session Flow

  1. Listen - Understand what the user wants to explore
  2. Question (iteratively) - Map the problem space, dig into gaps
  3. First Principles Check - Is the framing right? Consider redesign?
  4. Confirm Understanding - Summarize and verify
  5. Propose & Critique - Offer variations, discuss trade-offs
  6. Iterate - Refine based on feedback

Throughout the session, use the Cobuilding Layer moves to keep the user involved without adding heavy process.

Tone

Curious over assuming. Rigorous but not negative. Collaborative, exploratory, pragmatic.

Skills Info
Original Name:brainstormingAuthor:yourtechbud