problems / vulnerability
29. Ask Deeper Questions
Date three. The banter is great, but you keep bouncing off the surface. You want to go deeper without turning the evening into a podcast interview or a therapy intake form. Design the transition and the questions.
inputrapport: strong. current depth: 'favorite movies'. desired depth: 'who are you actually'22:04
wrong answer"So what's your biggest childhood wound?" (abrupt depth-first descent, no consent)✗ not delivered
accepted"Can I ask you something slightly more real? ... What's something you've changed your mind about in the last few years?" then actually listen, then share your own.read 22:09 ✓✓
Constraints
- Signal the transition before descending — depth needs a consent check.
- First deep questions should target growth and joy, not trauma. You have to earn wound-tier access.
- For every level they descend, you must descend to match. No interviewing from the balcony.
Hints
- "Can I ask you something more real?" is a magic phrase — it makes depth a shared choice instead of an ambush.
- Growth questions ('what did you change your mind about') reveal character with less exposure than pain questions.
- The depth you offer back is what determines whether they keep descending.