Nothing Fancy

“Where are you from and what was your upbringing like?”

This is often one of his first questions, used to establish the guest's backstory and origins.

“What made you decide you wanted to get into [your field]?”

He asks this to understand the initial spark or motivation behind a guest's career choice.

“What was that feeling like, achieving that major success?”

He uses this to capture the emotional peak of a guest's career before exploring the struggles.

“At what point did you decide to go pro or take it to the next level?”

This question targets the specific moment of commitment in a guest's professional journey.

“What was your mindset like when you [went through a major transition]?”

A go-to question for understanding the guest's internal state during a pivotal life change.

“Why don't you [do a common practice in your field, like watch old fights]?”

This question surfaces a guest's unique mindset or philosophy by questioning a common assumption.

“Did you ever struggle with your identity or feel like you had to pick a side?”

He asks this to probe into deeper themes of self-acceptance and personal history.

“What kind of pressure comes with being [a specific identity] in your industry?”

Used to explore the unique professional and personal challenges a guest has faced.

“What was it like on your way to your first [pivotal event, like an AA meeting]?”

This question focuses on the guest's feelings and thoughts leading up to a moment of change.

“How did you get the opportunity to [have a specific major experience]?”

He asks this to uncover the process and story behind a significant career milestone.

“What do you feel you learned the most from [a specific mentor]?”

This question is used to highlight the impact of key relationships on the guest's development.

“What's harder: getting sober or rebuilding who you are afterwards?”

He poses this kind of comparative question to draw out insights on the long-term challenges of recovery.