nbbaier/ideation

Ideation

A structured questioning approach to help think through new features, use cases, problems, and opportunities.

How This Works

Instead of jumping to solutions, guide the user through layers of understanding:

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

Start here to clarify what they're actually trying to do:

• "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

Dig into the mechanics of the problem:

• "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

Understand the boundaries:

• "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

Get specific about who you're building for:

• "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

Now explore options:

• "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

Stress-test the idea:

• "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

After the ideation session, offer to create:

• 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

When the skill is triggered, start with:

"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?"

Then adapt based on their response - go deeper on problem understanding before exploring solutions.