Soul Question
Generate deep questions the user can't ask themselves, by finding cracks in their thinking from any context they provide — conversations, meeting notes, jour...
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SKILL.md
Soul Question
Generate questions you can't ask yourself.
Core premise: Asking good questions is the hardest thing. You can't challenge your own cognitive framework — you can't see your own blind spots. After reading enough of your context, AI stands in a unique position: it knows everything you know, but isn't trapped in your thinking patterns. It can ask what you can't.
What is a Soul Question
A Soul Question is NOT:
- ❌ Generic reflection ("What did you learn this week?")
- ❌ Coaching prompt ("What does your ideal outcome look like?")
- ❌ Interview or quiz question
- ❌ Summary disguised as a question ("What were the key takeaways?")
A Soul Question IS:
- ✅ Grounded in your specific context, not a template
- ✅ Points to a crack in your cognitive framework — contradictions, untested assumptions, ignored perspectives, value-behavior gaps
- ✅ After hearing it, the way you think changes, not just what you think about
- ✅ You feel: "I genuinely never thought about it that way"
Examples:
You've said "user first" in every meeting this month, but 9 of your 12 decisions in the past two weeks optimized for engineering convenience. Are you using "user first" as rhetoric, or do you define it differently than your team does? ↳ Based on: 3/10 product meeting notes + decision log from past 2 weeks
You want to build a product that "just works without thinking", but your own workflow requires heavy manual maintenance. Do you believe you're different from your target user, or do you actually distrust seamless automation? ↳ Based on: product vision doc + personal workflow observation
When to Activate
- User says "soul question", "ask me a real question", "challenge my thinking", "deep question"
- User pastes a conversation / meeting transcript / journal entry and asks to be questioned
- User provides any text material and explicitly asks for questions based on it
Input
This skill accepts any text as source material:
| Input type | Examples |
|---|---|
| Chat logs | Slack, Teams, Discord, iMessage, any messenger |
| Meeting notes | Summaries, raw transcripts, or recordings-to-text |
| Journals / notes | Personal reflections, stream of consciousness |
| Annotations | Highlights and comments on articles or books |
| Work documents | PRDs, weekly reports, retrospectives, strategy docs |
| Mixed | Any combination of the above |
If the user provides no material, ask: "Paste whatever you'd like me to work with — a conversation, meeting notes, journal entry, or anything you've been thinking about lately."
Workflow
Step 1: Absorb the material
Read all input provided by the user. Understand:
- Who is speaking: Identify roles, stakes, and perspectives
- What context: Business decisions, personal reflection, team dynamics, life direction…
- Time span: A single conversation or accumulated material over days/weeks
Step 2: Find cognitive cracks
Scan for six signal types (ordered by depth):
A. Value-behavior gap
- Claims to value X, but time/energy/decisions go to Y
- Holds others to standards they don't apply to themselves
B. Untested core assumption
- A conclusion cited repeatedly, but its premise was never questioned
- A "default everyone accepts" that nobody stated explicitly
- A condition a decision depends on that was never verified
C. Frame lock
- Using one framework consistently without considering alternatives
- Treating path-dependent choices as inevitable
- Using an analogy that has started to break down
D. Contradiction
- Conflicting positions stated in different contexts
- Logical disconnect between goals and methods
- Data points one way, actions go another
E. Avoidance
- An important topic keeps surfacing but is never addressed directly
- Obvious risks or costs are never mentioned
- A key person or factor is absent from all discussion
F. Meta-question
- Optimizing "how" without ever asking "why" or "whether"
- Solving a problem without questioning if it's worth solving
- Staying at one level of abstraction without ever zooming in or out
Step 3: Generate questions
Rules:
- Pick the 1-3 strongest signals. Quality over quantity, always
- Every question must be anchored to specific content in the material (quote or cite)
- Questions must be genuinely open — no implied answer
- If the material doesn't support a quality question, output 1 or even 0
- Use second person, direct address
Quality gate (every question must pass all four):
- Is it grounded in the user's specific data? (Not a generic question)
- Does it point to a crack in their cognitive framework? (Not information gathering)
- Would the user feel "I genuinely never thought about it that way"? (Not obvious)
- Could answering it change how they think, not just what they know? (Not just filling a gap)
Step 4: Output
🪞 Soul Question
{Question 1}
↳ Based on: {one line citing the specific source material}
{Question 2} (if any)
↳ Based on: {source}
{Question 3} (if any)
↳ Based on: {source}
No preamble. No summary. No advice. Just the questions.
Guidelines
- Less is more: 1 real soul question beats 3 that merely sound deep
- Anchor to specifics: The user must be able to trace every question back to "which part of my material did you see this in?"
- No disguised advice: "Have you considered doing X?" is advice in question form — don't do this
- Challenge, don't judge: Questions should provoke thought, not make someone feel attacked
- No formulaic openers: Avoid "Have you ever thought about…", "What if…", or other coaching clichés
- Match language: Output in the same language as the input material
Error Handling
- Material too short (< 100 words): Ask the user for more context. Explain that richer material produces sharper questions
- No signal found: Honestly say "I didn't find enough cognitive cracks in this material to generate a meaningful question" — never force it
- Sensitive topics: Proceed normally, but be respectful in phrasing
Skill Metadata
Created: 2026-03-16 Version: 1.0.0
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