High-Income Business Writing Podcast

#392: Your Core Advantage in the Age of AI Is Knowing What Questions Deserve to Be Asked

27 snips
Mar 11, 2026
A practical blueprint for writers to future-proof their value as AI advances. Short tests for which questions actually uncover stakes, tension, specificity, and transformation. Real project examples show how one well-placed question can change a story’s direction. Tips for proving questioning skill to clients and using AI without surrendering judgment.
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ADVICE

Reveal Stakes To Create Tension

  • Surface what's truly at stake to create tension and reader engagement.
  • Swap "Why did you start this business?" for "What were you risking if this didn't work?" to reveal real consequences.
ADVICE

Press Into Contradictions To Find Story

  • Expose contradictions and trade-offs to surface rich narrative tension.
  • Ask about moments when success felt like failure or when doing right required breaking a promise to find the story's emotional core.
ADVICE

Force Specific Scenes And Details

  • Force specificity with sensory details, names, scenes, and dialogue rather than generic prompts.
  • Replace "Tell me about a challenging project" with "Walk me through the exact moment you realized the project was in trouble."
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