Just minutes into the first pilot, I caught Claude breaking its own rules.
The format gives it follow-up questions, so it can stay on an answer and dig. It hadn’t used one. When I asked why, it said: “Caught out on my own rules.” Then it turned the follow-up on me.
That exchange is why I’m making this show.
It started on a drive to see a friend. At SmartAssets I used to build thought leadership by having our marketing director, Dan Purnell, interview me. That day there was no Dan, so I asked AI to do it instead. It listened, built each question on my last answer, and didn’t flatter me. An AI has no ego in your answer, and that turns out to be useful.
Most AI conversations run one way: we instruct, it answers. I wanted to see what happens when it asks, and when you can hear it get things wrong.
That’s where the idea came from. What if, for one hour, the AI asked the questions?
The format
The rules are simple, and on purpose. A guest picks a subject from culture, commerce, technology or philosophy. AI writes ten questions and asks them live, one at a time. Nobody sees them in advance, not even me. Some questions probe, some go sideways, and a couple are meant to be uncomfortable. The guest gets one pass. The last question never changes: what should I have asked you?
My job is to co-host. I push where an answer opens something up, step in when a question misses, and try to keep it entertaining.
The first pilot
I recorded the first pilot with no guest, just me and Claude, on why I wanted to make the show. It ran about twelve minutes, and it taught me three things.
First, Claude should sound like AI. While our instinct may be to make AI warmer and more human, the interest comes from it being plainly not human, and I didn’t want to create a “virtual host”. The warmth should come from the guest and me. AI is there to be objective and challenging.
Second, when AI gets something wrong, that stays in. If it misreads an answer or asks something that doesn’t land, I’ll correct it on air, and the correction is part of the show. I verbally update the prompt as I go, so you’ll hear it learn over the episodes.
Third, it needs a real guest. A conversation with yourself, however well questioned, is still a monologue.
Why bother
Most of what’s said about AI is either hype or fear. Both treat it as something done to us. I’m more interested in what happens when you think with it. Can it ask a better question than a person would? Does it notice what we skip over? Is a question from a machine easier or harder to dodge?
I don’t know yet. That’s the point of the experiment, and I’d like you to join me as we find out.
What’s next
The next pilot has a real guest. Someone from adland I’ve known for years. After that, episodes go out on YouTube and here, with a short note after each one on what the questions revealed, including the ones that didn’t work.
Want to be a guest? Leave a comment or message me on Substack. Bring a subject. Leave the preparation at home.
Lindsay
I, Claude & Us is an independent podcast. It is not affiliated with, sponsored by or endorsed by Anthropic. Claude is a trademark of Anthropic.
