Sometimes you just need to be asked

I’ve always appreciated the spontaneous answers that pop out when people ask me questions. It leads to responses that it’s hard to manufacture on your own.

But it was rare. You’d have to wait for an interview, some client work or a thoughtful friend to show up.

Until now. Open your AI of choice (I used 4o in this example) and share an idea you’re interested in. Tell it to ask you 4 questions.

i wrote a linkedin post earlier this week and i want to expand it into a newsletter. i shared it after watching Tyler Cowen being interviewed by David Perell. i want you to ask me 4 questions, one at a time, that will help flesh out the ideas and bring more of my personal perspectives into play. here’s the post: …

Be sure to add some rough notes so it has something to go on.

Here are the 4 questions I got asked:

• 1. What specific part of the conversation sparked a strong reaction in you—curiosity, agreement, disagreement, excitement? Pick one moment or quote if you can. Something that made you pause or nod or even frown. We’ll use that as a hinge point.
• 2. How does this change your own learning habits or aspirations? Are you already using AI this way—or does this open up a shift in how you read, write, or study? How might this reshape your intellectual routines, or the way you explore a topic like Vipassana, burnout, or leadership?
• 3. What does this mean for your readers? You write to share insight, to help others think and feel more clearly. How might this conversational approach to learning—and your embrace of it—shape what you write, how you write, or even how you encourage others to engage with your work?
• 4. What do you think we risk losing in this new way of learning? Speed, efficiency, and companionship are powerful. But is there something older or slower or messier that you want to defend or hold onto, even as you embrace this new frontier?

After I typed each answer, it gave a summary and then moved on to the next question. Each time I answered I got a little dopamine bump.

You can then ask it to put the answers together into a rough draft. It’s fascinating to see what themes emerge. I wouldn’t use the resulting draft as is, but the difficult work is done.

As you can see, ChatGPT also knows things about me. That means it can pull in my other interests when asking questions, like meditation and burnout, making it more personal.

Having the questions asked one at a time and needing to answer on the spot also creates a little rush. It helps you lean into getting your thoughts down without over-thinking.

Sometimes you just need to be asked.

Thanks to Gavin for introducing me to this pattern.