ask-better-questions

Ask better questions

Transform shallow questions into powerful ones by running them through 7 Socratic lenses.

Quick start

Take the user's question or problem and apply the 7 lenses:

1. Challenge — What's wrong with my reasoning?
2. Unconstrained — What if I had infinite resources?
3. Meta — What didn't I ask?
4. Uncertainty — Where am I wrong?
5. Inverse — What's the opposite?
6. Reframe — How would a [domain expert] see this?
7. Assumptions — What am I optimizing for implicitly?

Example:

User's question: "How do I build better retention?"

After 7 lenses:

• "What flaws are in my retention model?"
• "What if I had unlimited budget to keep users?"
• "What signals am I ignoring that predict churn?"
• "Where's my retention strategy failing that I haven't admitted?"
• "How would I maximize churn instead?"
• "How would a behavioral psychologist reframe retention?"
• "Am I optimizing for retention or engagement?"

Pick 1-2 that resonate. Ask those instead. Get better answers.

How to use

Approach 1: AI-guided (interactive) — default

1. User gives their problem: "I'm trying to..."
2. Apply all 7 lenses and present reformulations
3. User picks which ones matter
4. Explore the chosen lenses deeper, then synthesize

Approach 2: Self-guided (manual)

1. Present the 7 lenses as a framework
2. User applies each lens themselves
3. Help them refine the 1-3 that feel most important

Approach 3: Deep dive (iterative)

1. Start with one lens (e.g., Inverse)
2. Explore that lens thoroughly
3. Move to the next lens
4. Synthesize across lenses for comprehensive insight

The 7 lenses — quick reference

Lens	Reframes	Best for
Challenge	Weaknesses in your approach	Catching blind spots
Unconstrained	What's truly wanted, not constrained	Vision-setting, discovering what matters
Meta	What you're missing	Completeness checks, edge cases
Uncertainty	Admitting what you don't know	Risk awareness, intellectual humility
Inverse	Opposite direction	Discovering root causes, hidden assumptions
Reframe	Fresh perspective from another field	Novel solutions, pattern recognition
Assumptions	What you're actually optimizing	Alignment checks, goal clarification

For detailed guidance, prompts, and examples for each lens, read references/lenses.md.

When this skill helps most

• Before asking AI anything important — refine the prompt first
• When stuck on a problem — a different lens often unsticks you
• Decision-making — expose hidden trade-offs
• Project planning — catch unspoken goals
• Learning — go deeper than surface answers
• Creativity — challenge assumptions to unlock new ideas

Common patterns

Surface question into 3 refined questions

Surface: "Should I hire more engineers?"

Lens 1 (Challenge): "What are the real constraints on our output — is it headcount?"
Lens 4 (Uncertainty): "Where am I wrong about engineering capacity?"
Lens 7 (Assumptions): "Am I optimizing for velocity or code quality?"

Ask these 3 instead of the surface one.

Stuck decision

Stuck on: "Do I pursue this project or not?"

Lens 6 (Reframe): "How would a CFO see this? A designer? A customer?"
Lens 5 (Inverse): "What if I actively avoided this? What's the fear?"
Lens 3 (Meta): "What am I not asking that would help?"

Run through these lenses first; the decision often clarifies.

Brainstorming breakthrough

Brainstorming: "How do we improve onboarding?"

Lens 5 (Inverse): "How would we maximize onboarding failure?"
Lens 2 (Unconstrained): "What if onboarding took 10x longer but was perfect?"
Lens 6 (Reframe): "How would a game designer think about this?"

These unconventional angles unlock creative solutions.

Lens combinations

Trio for clarity:

• Lens 7 (Assumptions) + Lens 3 (Meta) + Lens 1 (Challenge)

Trio for creativity:

• Lens 5 (Inverse) + Lens 6 (Reframe) + Lens 2 (Unconstrained)

Trio for risk:

• Lens 4 (Uncertainty) + Lens 5 (Inverse) + Lens 3 (Meta)

Tips

• Start with 1 lens, not all 7 — too many at once overwhelms
• Some lenses matter more than others for any given problem — lean into the 2-3 that feel obvious
• Iterate — first refinement begets second refinement
• Trust your gut — if a lens doesn't resonate, skip it