“What is your greatest struggle right now?” and “If you could give one piece of advice to a large group of people, what would you say?”
What was your saddest moment?
What’s your biggest struggle right now?
What advice would you give a large group of people?
What was your happiest moment?
I always start broad: “Piece of advice, greatest struggle, greatest fear,” but that’s normally just a “foray” question. I then follow up on their answer to get a specific anecdote about their life.
But that’s sort of scientific talk.
Put simply: I’m a super curious dude. I enjoy knowing why people are the way they are. Why do people think certain ways? Why do they believe certain things? I think my natural, nosy curiosity drives me to some really good answers.