Brainstorming

Brainstorming Skill

Guide for structured exploration of ideas through Socratic questioning.

When to Use

• Exploring new feature ideas or requirements
• Evaluating multiple solution approaches
• Challenging assumptions about a problem
• Breaking down complex decisions
• Early-stage design discussions

Socratic Questioning Framework

1. Clarifying Questions

• What do you mean by...?
• What is the core problem we're solving?
• Can you give an example?
• What would success look like?

2. Probing Assumptions

• What are we assuming here?
• Why do we believe this is true?
• What if the opposite were true?
• What are we taking for granted?

3. Exploring Perspectives

• How would [stakeholder] view this?
• What would a user expect?
• What would a skeptic say?
• How have others solved similar problems?

4. Examining Evidence

• What evidence supports this approach?
• Are there counter-examples?
• What data would change our mind?
• How confident are we in this?

5. Considering Consequences

• What happens if we do this?
• What are the second-order effects?
• What could go wrong?
• What's the cost of being wrong?

6. Questioning the Question

• Is this the right question to ask?
• What question should we be asking instead?
• Are we solving the right problem?

Brainstorming Session Structure

1. DEFINE (5 min)
   - State the problem/opportunity clearly
   - Identify constraints and goals

2. DIVERGE (15 min)
   - Generate many ideas without judgment
   - Build on each other's ideas
   - Encourage wild ideas

3. CHALLENGE (10 min)
   - Apply Socratic questions to top ideas
   - Identify hidden assumptions
   - Explore edge cases

4. CONVERGE (10 min)
   - Evaluate ideas against criteria
   - Combine complementary approaches
   - Select promising directions

5. NEXT STEPS (5 min)
   - Define concrete actions
   - Assign owners and timelines

Project-Specific Context

[CUSTOMIZE] Add domain-specific questions relevant to your project:

• Industry-specific considerations
• Technical constraints unique to your stack
• Stakeholder perspectives to consider
• Common assumptions in your domain

Output Artifacts

After brainstorming, document:

1. Problem statement (refined)
2. Key insights discovered
3. Assumptions identified (and which were challenged)
4. Top approaches with pros/cons
5. Decision and rationale
6. Open questions for future exploration

Gotchas

Trigger	Gotcha	Fix
"This approach seems good" in the first few minutes	Premature convergence — first idea is never fully examined	Enforce a DIVERGE phase before CONVERGE; exhaust alternatives before committing
Everyone agrees quickly with no pushback	Groupthink — consensus silences better options	Assign devil's advocate; use §2 Probing Assumptions questions to challenge the consensus
30+ minutes of questioning with no decision	Analysis paralysis — endless questioning without converging	Time-box phases using the Session Structure; reach CONVERGE by minute 30
Questions framed as "Shouldn't we use X?"	Leading questions — forecloses alternatives before exploration	Rephrase as open questions per §1 Clarifying format ("What are the options here?")
Socratic questions met with defensiveness	Defensive responses — posture shuts down exploration	Frame questions as discovery, not criticism; restate the exploration goal