Presented at PopTech 2025, Washington DC

Most people think of AI as a tool for generating text — a shortcut that outsources the creative process to a machine. Writer and educator Jay Dixit says we need to flip the script and let the AI ask us questions for a change.

In this PopTech talk, OpenAI alum Jay Dixit explains how to use AI not as a ghostwriter, but as a writer’s room, creative coach, and iterative thinking partner — an approach he calls “Socratic AI.” Instead of asking AI for answers, you use it to ask YOU questions to surface your OWN best ideas.

The hardest part of writing isn’t typing sentences — it’s figuring out what to write before you write it. Drawing on his experience teaching writing at Yale and leading OpenAI’s writing community, Jay demonstrates “reverse interviewing,” a technique that helps writers overcome blocks, uncover their best stories, and actually finish their creative projects.

Includes a Q&A with behavioral economist Dan Ariely on the value of productive struggle and how to protect the serendipitous, exploratory parts of the writing process.

About the Speaker: Jay Dixit is former Head of Community for Writers at OpenAI and a champion of ethical, human-centered AI. He’s taught writing and storytelling at Yale University, and his writing has appeared in The New York Times, Rolling Stone, and Psychology Today. Jay now runs Socratic AI, an AI training and education consultancy that teaches knowledge workers, companies, and universities how to use AI more thoughtfully and ethically to support—not replace—human creativity.

Socratic AI in Action: Excavate Your Most Revealing Story

A sample Socratic AI prompt to help you remember stories from your own life

Jay’s Prompt for PopTech: Memory Excavation

2 Paste 3 Enter Socratic mode 
Hi! Help me surface a vivid, specific true story from my life — something real and cinematic that reveals who I am and what I care about at my core. A meaningful, entertaining story I can tell here at PopTech that’s both entertaining to listen to, but also makes people lean in and think, “Wow, now I get who you are.”

Ask me 10 gentle, memory-warming questions, one at a time, that help me REMEMBER a story — not choose one in advance.

Your questions should:

- Be concrete, emotional, and sensory — the kind of questions that pull me into a moment, not an idea
- Start small and build toward tension, surprise, or change.
- Help me remember experiences where I was fully myself — challenged, moved, or changed.
- Sound like a curious, perceptive friend, not an interviewer.
- Never ask me for “a story” or “a lesson.” Just help me remember meaningful moments from my own life!
- Let the meaning emerge naturally through the memory, rather than naming or interpreting it.

The goal:

To surface a moment that unfolds like a short film — full of emotion, texture, and transformation — and that quietly reveals what drives me or what I stand for.

First question to ask me:

“Can you remember a time your heart was pounding because you were about to say or do something risky but super important to you?”

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