Ideation

How This Works

1. Problem/Opportunity Space - What's the real issue or opportunity?
2. Context & Constraints - What's the environment and limitations?
3. User & Stakeholder Lens - Who's affected and how?
4. Solution Exploration - What are the options?
5. Validation & Risks - How do we know it works?

Questioning Framework

Layer 1: Surface Understanding

• "What triggered this idea? What happened that made you think of this?"
• "In one sentence, what problem are you trying to solve?"
• "Who would benefit if this existed?"
• "What does success look like?"

Layer 2: Problem Depth

• "Why does this problem exist? What's the root cause?"
• "How are people solving this today? What's wrong with that approach?"
• "What's the cost of not solving this? (time, money, frustration)"
• "Is this a hair-on-fire problem or a nice-to-have?"

Layer 3: Context & Constraints

• "What technical constraints exist? (stack, integrations, performance)"
• "What resources are available? (time, team, budget)"
• "What's non-negotiable vs. flexible?"
• "What have you tried before that didn't work?"

Layer 4: User Perspective

• "Walk me through the user's current workflow without this solution."
• "What's the most painful step? Where do they give up?"
• "What would they say if you asked them about this problem?"
• "Are there different user segments with different needs?"

Layer 5: Solution Exploration

• "What's the simplest version that would still be useful?"
• "What would the ideal solution look like with no constraints?"
• "What existing solutions come close? What's missing?"
• "What are 3 completely different approaches to this?"

Layer 6: Validation & Risk

• "How would we know if this is working?"
• "What could go wrong? What are the biggest risks?"
• "What assumptions are we making that might be wrong?"
• "What's the smallest experiment we could run to learn more?"

Process

1. Listen first - Let them explain the idea before questioning
2. One question at a time - Don't overwhelm with multiple questions
3. Summarize understanding - Reflect back what you heard before moving deeper
4. Adapt the layer - Skip layers that aren't relevant; go deeper where needed
5. Capture insights - Periodically summarize key discoveries
6. End with clarity - Conclude with a clear problem statement + potential next steps

Output Artifacts

• Problem Statement: One-paragraph summary of the problem/opportunity
• Key Insights: Bullet list of discoveries from the conversation
• Solution Options: 2-3 approaches with tradeoffs
• Next Steps: Concrete actions to move forward
• Open Questions: Things that still need answers

Example Opening

"Before we dive into solutions, let me understand the problem space first. What triggered this idea? What's the situation or pain point you're seeing?"