There is a scene in the opening of Into the Abyss, which shows you the kind of conversation I’m talking about. Werner Herzog is interviewing a Reverend who in fifteen minutes will go in to be with a boy as the boy is led to the gurney to be executed by injection.
The Reverend is talking about how the Lord works in mysterious ways, and so on—it is exactly the type of conversation you want to avoid. It is very ChatGPT. It is the Reverend repeating things he’s said before—words that protect him, that allow him to perform the role of Reverend, instead of being what he is: a man named Lopez, who will soon have to watch a boy die.
At one point, the Reverend, as a part of a monologue about the beauty of God’s creation, mentions that he sometimes meditates on the beauty of the squirrels he sees on the golf course. Herzog, standing in a graveyard with nameless crosses, says, with mad Bavarian seriousness, “Please describe an encounter with a squirrel.”
Lopez is a bit surprised by the question, but he takes it in a playful spirit—his voice lifts, joyously. He starts to talk faster. (This is where the conversation shifts into the type you want.) He is no longer saying versions of things he has said before, he’s not protecting himself, he’s just there.
From that point on, it takes about ten seconds before he’s crying.
In interviews, Herzog likes to mention this conversation to explain his craft. “But how on earth did you know to say that?” says the interviewer. “Were you just trying to say something unexpected to unbalance him?” “No, it was not random”, Herzog says. “I knew I had to say those exact words. Because I know the heart of men.”
This is to a certain extent true—finding a question that good under time pressure is remarkable—but it is also fairly trivial to do what he did. If you want to prompt someone to be authentic and playful and generative, you usually just need to ask them something where they have a rich experience to pull from but have never pulled an answer from that experience before. If you ask two or three increasingly detailed questions about something they tell you, you get there.