Here is a list of questions I love asking people I want to know more deeply, in no particular order. Work in progress.
What is the most valuable thing you can give to someone?
What makes you feel alive? What makes you die a little inside?
What is your life story in 5 minutes? 50 seconds? 5 words?
What is your biggest regret, and what are you doing about it?
What is something you've dreamed of doing, and why haven't you done it?
What is something you need to tell someone, and why haven't you told them?
How do you define success in your career? At a personal level?
Who is someone you look up to, and why?
What is an unpopular opinion that you hold?
What is the biggest problem facing society today?
If I really knew you, what would I know about you?