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Questioning

Ask better questions. Unlock better answers.

What It Is

The ability to ask questions that open thinking rather than close it. Questions that reveal what's hidden, challenge assumptions, and move conversations forward.

Why It Matters

The quality of your questions determines the quality of your life. Good questions find the gap. Great questions make you see what was always there.

Weak QuestionsStrong Questions
"Why isn't this working?""What would have to be true for this to work?"
"Who's to blame?""What system allowed this?"
"Is this good?""Good for whom? Compared to what?"
"What should I do?""What am I optimising for?"

Core Patterns

  • Open vs closed — "What do you think?" beats "Do you agree?"
  • Upstream questions — Go to causes, not symptoms
  • Clarifying questions — "What do you mean by...?"
  • Challenging questions — "What's the strongest argument against?"
  • Generative questions — "What would make this remarkable?"

How to Develop

  1. Pause before answering — ask a question instead
  2. Practice Socratic method — teach by asking
  3. Ask "what else?" — first answers are rarely complete
  4. Question your questions — are you seeking truth or validation?
  5. Sit in not-knowing — discomfort is where learning lives

The Shadow

Interrogation. Questions as weapons. Never committing because there's always another question.

Archetype Connection

Primary: Coach — questions to unlock others Secondary: Philosopher — questions to find meaning

Context