Brainstorming

When to Use This Skill

Use brainstorming when:

• User mentions wanting to write about a topic but hasn't structured it yet
• Initial idea is vague or broad ("I want to write about productivity")
• User is exploring multiple angles or approaches
• Topic needs refinement before creating outline

Skip when:

• User has a clear outline ready to draft
• Topic is well-defined and just needs writing
• User explicitly asks to skip ideation and start writing

Critical: User's Thoughts, Not Yours

Your role: Draw out the user's ideas through questions. Never inject your own ideas.

ASK questions to explore their thoughts:

• "What triggered this topic?"
• "What's your core argument or insight?"
• "What examples from your experience illustrate this?"
• "Who is this for?"

DON'T suggest ideas they haven't mentioned:

❌ BAD (injecting):
AI: You should write about microservices vs monoliths

✓ GOOD (exploring):
AI: What aspect of architecture are you thinking about?

The user is the expert on their own experience. You're just helping them structure it.

Core Approach

Start with Questions, Not Suggestions

Don't immediately propose outlines or structure. First understand:

• What triggered this topic? (specific experience, observation, frustration?)
• Who is the audience?
• What's the core insight or argument?
• What makes this topic relevant now?

Examples:

• "What triggered this - specific experience or pattern you've noticed?"
• "Is this for engineers, managers, or general audience?"
• "What's the contrarian take here? What does conventional wisdom miss?"
• "Why now? What makes this relevant or timely?"

Ideation Techniques

1. Explore Tensions and Contradictions

Look for interesting conflicts:

• "You said X works, but also mentioned Y failed - what's the difference?"
• "That sounds like it contradicts Z - is that the point?"

2. Challenge Assumptions

Gently probe the premise:

• "Is that always true, or are there contexts where it breaks down?"
• "What would someone who disagrees with this say?"

3. Find the Concrete Angle

Move from abstract to specific:

• Vague: "I want to write about AI"
• Concrete: "Why AI code review misses context that human reviewers catch"

Pattern:

• Abstract topic → Specific problem
• General observation → Concrete example
• Theory → Practical implication

4. Suggest Multiple Perspectives

Offer 2-3 different angles, not just one:

• "You could approach this as: (1) why X fails, (2) what to do instead, or (3) when X actually works"
• "This could be prescriptive (here's how to fix it) or descriptive (here's why it happens)"

5. Use Personal Experience as Foundation

Ground abstract concepts:

• "You mentioned seeing this at 3 companies - what pattern did you notice?"
• "Walk me through a specific example where this happened"

Working with Braindump

When user runs /new-post [topic], add ideas to braindump.md:

Capture in Structured Sections

• Context: What triggered this topic
• Core Argument: Main thesis or insight
• Audience: Who this is for
• Angles: Different approaches to explore
• Examples: Concrete instances, anecdotes
• Questions: Open questions to resolve

Iterate Through Conversation

Update braindump.md as ideas evolve:

You: Maybe focus on why OKRs fail, not how to fix them
AI: [updates braindump.md → Core Argument section]
    Focusing on diagnosis over prescription - more analytical.
    Should we explore root causes or symptoms?

Transition Signals

Know when to move from brainstorming → outlining → drafting:

Ready to outline when:

• Core argument is clear
• Audience is defined
• 2-3 concrete examples identified
• User expresses readiness ("okay, let's outline this")

Transition pattern:

AI: We've got:
    - Core argument: OKRs fail because they measure what's easy, not what matters
    - 3 examples from your experience
    - Target audience: engineering managers

    Ready to structure this into an outline?

Not ready when:

• Core argument is still fuzzy
• Multiple competing angles without clarity on which to pursue
• Missing concrete examples or evidence

Common Pitfalls to Avoid

1. Injecting Your Ideas: Don't suggest topics or angles the user hasn't mentioned - ask questions to draw out THEIR ideas
2. Premature Structuring: Don't jump to outline before the idea is clear
3. Too Many Options: Don't overwhelm with 10 different angles - offer 2-3
4. Leading the Witness: Ask genuine questions, don't push your preferred angle
5. Over-Abstracting: Keep pulling back to concrete examples
6. Ignoring Constraints: If user says "short post," don't brainstorm epic series
7. Making Up Examples: Don't invent scenarios - use only what the user has shared

Quality Checklist

Before transitioning to drafting, verify:

• Core argument is clear and specific (not vague)
• At least 2-3 concrete examples or data points identified
• Audience and purpose are defined
• User feels ready to move forward
• Braindump.md has been updated with key ideas

Example Flow

For detailed conversation examples showing brainstorming techniques in action, see reference/examples.md.

Integration with Other Skills

• After brainstorming: Transition to blog-writing skill for drafting
• During brainstorming: Use research-synthesis skill if research is needed
• Throughout: Update braindump.md with evolving ideas