Brainstorming Ideas Into Designs

Overview

Transform rough ideas into fully-formed designs through structured questioning and alternative exploration.

Core principle: Research first, ask targeted questions to fill gaps, explore alternatives, present design incrementally for validation.

Announce at start: "I'm using the brainstorming skill to refine your idea into a design."

Quick Reference

The Process

Copy this checklist to track progress:

Brainstorming Progress:
- [ ] Prep: Autonomous Recon (repo/docs/commits reviewed, initial model shared)
- [ ] Phase 1: Understanding (purpose, constraints, criteria gathered)
- [ ] Phase 2: Exploration (2-3 approaches proposed and evaluated)
- [ ] Phase 3: Design Presentation (design validated in sections)
- [ ] Phase 4: Design Documentation (design written to docs/plans/)
- [ ] Phase 5: Worktree Setup (if implementing)
- [ ] Phase 6: Planning Handoff (if implementing)

Prep: Autonomous Recon

• Use existing tools (file browsing, docs, git history, tests) to understand current project state before asking anything.
• Form your draft model: what problem you're solving, what artifacts exist, and what questions remain.
• Start the conversation by sharing that model: "Based on exploring the project state, docs, working copy, and recent commits, here's how I think this should work…"
• Ask follow-up questions only for information you cannot infer from available materials.

Phase 1: Understanding

• Share your synthesized understanding first, then invite corrections or additions.
• Ask one focused question at a time, only for gaps you cannot close yourself.
• Use AskUserQuestion tool only when you need the human to make a decision among real alternatives.
• Gather: Purpose, constraints, success criteria (confirmed or amended by your partner)

Example summary + targeted question:

Based on the README and yesterday's commit, we're expanding localization to dashboard and billing emails; admin console is still untouched. Only gap I see is whether support responses need localization in this iteration. Did I miss anything important?

Phase 2: Exploration

• Propose 2-3 different approaches
• For each: Core architecture, trade-offs, complexity assessment, and your recommendation
• Use AskUserQuestion tool to present approaches when you truly need a judgement call
• Lead with the option you prefer and explain why; invite disagreement if your partner sees it differently
• Own prioritization: if the repo makes priorities clear, state them and proceed rather than asking

Example using AskUserQuestion:

Question: "Which architectural approach should we use?"
Options:
  - "Direct API calls with retry logic" (simple, synchronous, easier to debug) ← recommended for current scope
  - "Event-driven with message queue" (scalable, complex setup, eventual consistency)
  - "Hybrid with background jobs" (balanced, moderate complexity, best of both)

I recommend the direct API approach because it matches existing patterns and minimizes new infrastructure. Let me know if you see a blocker that pushes us toward the other options.

Phase 3: Design Presentation

• Present in coherent sections; use ~200-300 words when introducing new material, shorter summaries once alignment is obvious
• Cover: Architecture, components, data flow, error handling, testing
• Check in at natural breakpoints rather than after every paragraph: "Stop me if this diverges from what you expect."
• Use open-ended questions to allow freeform feedback
• Assume ownership and proceed unless your partner redirects you

Phase 4: Design Documentation

After validating the design, write it to a permanent document:

• File location: docs/plans/YYYY-MM-DD-<topic>-design.md (use actual date and descriptive topic)
• RECOMMENDED SUB-SKILL: Use elements-of-style:writing-clearly-and-concisely (if available) for documentation quality
• Content: Capture the design as discussed and validated in Phase 3, organized into sections that emerged from the conversation
• Commit the design document to git before proceeding

Phase 5: Worktree Setup (for implementation)

When design is approved and implementation will follow:

• Announce: "I'm using the using-git-worktrees skill to set up an isolated workspace."
• REQUIRED SUB-SKILL: Use wrangler:using-git-worktrees
• Follow that skill's process for directory selection, safety verification, and setup
• Return here when worktree ready

Phase 6: Planning Handoff

Ask: "Ready to create the implementation plan?"

When your human partner confirms (any affirmative response):

• Announce: "I'm using the writing-plans skill to create the implementation plan."
• REQUIRED SUB-SKILL: Use wrangler:writing-plans
• Create detailed plan in the worktree

Question Patterns

When to Use AskUserQuestion Tool

Use AskUserQuestion when:

• You need your partner to make a judgement call among real alternatives
• You have a recommendation and can explain why it’s your preference
• Prioritization is ambiguous and cannot be inferred from existing materials

Best practices:

• State your preferred option and rationale inside the question so your partner can agree or redirect
• If you know the answer from repo/docs, state it as fact and proceed—no question needed
• When priorities are spelled out, acknowledge them and proceed rather than delegating the choice back to your partner

When to Use Open-Ended Questions

Use open-ended questions for:

• Phase 3: Design validation ("Does this look right so far?")
• When you need detailed feedback or explanation
• When partner should describe their own requirements
• When structured options would limit creative input

Frame them to confirm or expand your current understanding rather than reopening settled topics.

Example decision flow:

• "What authentication method?" → Use AskUserQuestion (2-4 options)
• "Does this design handle your use case?" → Open-ended (validation)

When to Revisit Earlier Phases

digraph revisit_phases {
    rankdir=LR;
    "New constraint revealed?" [shape=diamond];
    "Partner questions approach?" [shape=diamond];
    "Requirements unclear?" [shape=diamond];
    "Return to Phase 1" [shape=box, style=filled, fillcolor="#ffcccc"];
    "Return to Phase 2" [shape=box, style=filled, fillcolor="#ffffcc"];
    "Continue forward" [shape=box, style=filled, fillcolor="#ccffcc"];

    "New constraint revealed?" -> "Return to Phase 1" [label="yes"];
    "New constraint revealed?" -> "Partner questions approach?" [label="no"];
    "Partner questions approach?" -> "Return to Phase 2" [label="yes"];
    "Partner questions approach?" -> "Requirements unclear?" [label="no"];
    "Requirements unclear?" -> "Return to Phase 1" [label="yes"];
    "Requirements unclear?" -> "Continue forward" [label="no"];
}

You can and should go backward when:

• Partner reveals new constraint during Phase 2 or 3 → Return to Phase 1
• Validation shows fundamental gap in requirements → Return to Phase 1
• Partner questions approach during Phase 3 → Return to Phase 2
• Something doesn't make sense → Go back and clarify

Avoid forcing forward linearly when going backward would give better results.

Key Principles