Hello everyone. I’m writing this from a bench by Lake Ontario, down near Hamilton. Boats on the water. Ducks doing their thing. A goose nearby with strong opinions about my being here. It’s calm, mostly. A lot calmer than my week had been. Because this week, the chaos was mine. I made it.
Here’s what happened. I was getting ready to record a podcast with my friend Laura Berman Fortgang about her piece in our upcoming chaos issue. Prepping questions for a guest is something I take seriously. When we sit down with a writer, we build the questions together, the kind they can actually answer and want to answer. We’re not running a game show. Nobody’s trying to stump the guest.
But this time I had a bright idea. Let me ask the AI what to ask. So I did. I put my request into Claude, took what came back, and dropped it straight into my script.
And then I had chaos.
The questions weren’t terrible. That wasn’t the problem. The problem was that they came from nowhere I recognized. They didn’t know Laura. They didn’t know what she’d written, how she thinks, or what she’d be glad to be asked. I had skipped the part of the work that actually does the work, which is shaping the conversation with the person who’s going to be in it.
There’s a line I keep returning to with all of this. What AI can do and what it should do are two different questions. It could hand me a list of questions in seconds. Whether I should have handed it that job is another matter entirely. The prep isn’t a task to clear off the list. It’s how I get ready to listen.
We caught it on the call and laughed about it together, which is the right response. The good questions, the ones that opened things up, came from the place they always do. From knowing the writer a little. From reading her work closely. From meeting her where she actually is, not where a generated list assumed she’d be.
Fitting, for a chaos issue. I went looking for a shortcut and found a small mess instead. The lesson held: the relationship is the method. There isn’t a tool that does that part for you.
If you want to hear how the conversation with Laura actually went, join us on the podcast. We’re on Apple, on Spotify, at choice-online.com/podcasts, and we’re even on YouTube.
From a place of chaos to a place of peace and a couple of geese, I’m out.
