The Socratic
Approach to AI

One example: I flip the script and let the AI ask the questions for a change. Instead of prompting AI, I get the AI to prompt me, asking probing questions that get me thinking, push me to make new connections, and surface my own best ideas, stories, and examples. I call it the Socratic Interview.

Staring at a blank page trying to compose the perfect sentence is hard. Answering questions about your own life and insights is easy. The Socratic interview allows you to start a writing or thinking session with a free-flowing conversation that elicits your own creativity — a conversation where all the ideas come from you.

I know from my years as a journalist that there’s something magical about having someone ask you questions.

Being asked a question gets your creative juices flowing in a different way than just being in your own head trying to figure out what to write.

I think back to when I was an editor at Psychology Today. A big part of my job was interviewing psychologists and neuroscientists about their research.

Usually they were more scientist than storyteller. I’d ask about a research finding, and what they’d say back was way too vague, abstract, or technical to be interesting to the average reader.

So I’d ask them to explain the scientific principles in ways ordinary readers would understand.

“What about this would blow an average person’s mind if they learned about it?” “What are you doing differently in your own life since you discovered this finding?” “What actual advice do you have for someone reading this?” “Can you think of a story from your own life that illustrates this?”

Usually they’d say something like, “Yeah, good question! A personal story, I’d have to think about that. Let me get back to you on that.”

Then I’d use my classic reporting technique: staring at them blankly. “Oh, you want me to think of one right now?” they’d say. “Gosh, I don’t know. That’s hard.”

Eventually they’d have to fill the silence. “I mean OK, there was one time back when I was a post-doc. I’m not sure if I should share this, but what the hell. So I was at the lab working late one night when I heard a knock...”

I’d keep pressing like that through the whole interview. Pushing them to be ever more concrete. “Hmm, that’s pretty abstract, I’m not sure an ordinary reader would really get what you mean. Can you think of a concrete example? For real, tell me a story from your own life.”

Pushing, waiting for an answer, not letting them off the hook. Expressing my curiosity, asking thoughtful follow-up questions, waiting patiently, and never settling for a vague or boring answer.

The scientist was always delighted to engage because they could see that I was genuinely interested in understanding their research. “You’re really interested in my work? You really think readers would be interested?” “Definitely. But we have to spell out why it’s relevant for their lives.”

My questions invited them to reach deeper. I gave them time to think deeply, make new connections, to think back and recollect stories they’d forgotten they had (or things that had happened to them that they’d never thought to tell as stories).

My attitude was: You’re a brilliant scientist. I’m happy to wait a sec while you come up with a brilliant insight.

At the end of the interview, the psychologist or neuroscientist would always say the same thing: “That was amazing. I haven’t thought about that for years! You really pushed me to think of a concrete example. I’m going to use that story for sure when I present my poster at next month’s conference. Maybe for my TED talk too. And definitely the next time I’m interviewed on TV.”

I was interviewing them for my own selfish reasons — because I needed quotes for the article I was writing. But the scientists always walked away thanking me — and it was because I’d asked thoughtful, insight-inducing questions that forced them to think in a new way.

Not to diminish my abilities as an interviewer, but it turns out AI also excels at asking thoughtful questions.

The Socratic approach to AI is a way of helping with the cold start problem: that paralyzing deer-in-headlights moment when you’re staring down the blank page.

You’re clicking and unclicking your pen, asking yourself: “What is the perfect first sentence that adequately captures the rich and hilarious history of my friendship with Tim in a tone that’s both loving and gently roasting?” It can feel almost impossible.

But being asked a question like “What’s the most embarrassing thing Tim ever did?” gets you thinking a different way. Your mind immediately starts surfacing memories and conversations.

That’s why there’s such a thing as an interview. Your mind doesn’t automatically passively produce brilliant insights at all times (though sometimes it does). But if you want to think creatively, it helps to understand that your mind responds to questions.

I might not know the answer before I’m asked, but if you ask me a question, then I’m thinking, “Oh, good question! Let me think that through. OK, here’s what I would say.” And then I give you something new I hadn’t thought about before.

If I’m interviewing a psychologist and I say, “Here’s a new finding in psychology. Can you think through what an ordinary person should do differently to improve their life based on this research,” they’re then forced to think of an answer to a question they might not have considered before. Being asked insight-inducing questions leads you to make new connections and come up with ideas you might not have had otherwise.

Writing is hard. Answering questions helps you excavate your own mind for material — the forgotten story, the funny thing you said at a cocktail party, the time you phrased something so perfectly. Talking it out by answering questions allows you to surface all those fleeting thoughts and clever locutions that flickered across your consciousness but never got captured on the page. The Socratic approach to AI is a way to retrieve the amazing material that’s already in your head, but it works just as well to ask probing questions that push you to think more deeply, make new connections, and have creative insights you wouldn’t have had just sitting there. There’s something about being asked a question by someone else that forces you to think in new ways. Things surface, ideas surface, insights come together when you’re asked questions in ways that they don’t when you’re just staring at a page and thinking, “Oh man, what should I write?” You still have to do the hard work of writing yourself — AI should never replace the creative process — but instead of starting with a blank page, you start with a rich repository of stories, examples, and details that came from your own mind, in your own voice and your own words.