800 Conversations
Eight hundred recorded interviews with founders, executives, and engineers across two years. The single most useful thing I learned was not about AI. It was about how people actually talk when they stop performing.
I have recorded about eight hundred conversations in the last two years.
Most of them were with founders, executives, marketers, engineers. Some of them were on stage. Most of them were on Zoom. A few were at hackathons in basements. The point of the project was not really one project. The point was that I had figured out, by accident, that I was the person in most rooms who was the most interested in hearing how the other person actually thought.
What I learned, after eight hundred of these, is mostly not about AI. It is about how people sound when they stop performing.
The first ten minutes are a costume
The first ten minutes of an interview are the part the person rehearsed. They didn’t rehearse on purpose. They rehearsed because they have given the same elevator pitch four hundred times this year and the words are now ahead of them. They are saying the words. The words are saying themselves.
If you stop the interview at minute ten you get the press release. The press release is not interesting. It is interesting that the person memorized one. Nothing else.
The interview starts at minute eleven. It starts when the person realizes you are not going to ask them the next question on the press tour. It starts when you ask the question that nobody asks them and they have to actually look at the answer. The look is the part the audience wants. The look is the part the camera wants. The look is the entire reason you are in the room.
The pivot
The single move that consistently gets a person to drop the costume is: ask what they do. Let them tell you. Then, mid-conversation, pivot. Ask why they personally do it. Not why the company does it. Why this person, in this chair, on this Tuesday, decided to spend their life on this.
The first version of that question is the one the interview wants. The second version is the one you cannot ask in the first ten minutes because the person has not stopped performing yet. By minute twenty, they have. By minute twenty, “why do you do this” lands like a real question, because at that point the conversation has earned the right to ask one.
The silence
The other move is silence.
The hardest move in interviewing is to ask a hard question and then say nothing. Most people, including most professional interviewers, fill the pause. They ask a softening follow-up. They make a joke. They restate the question. They are trying to take the discomfort off the guest. The discomfort is the part you wanted. Take it off and the answer flattens.
The silence is the most generous thing you can give a guest. You are saying, with your body: I am not going to rescue you. The answer you are about to give is yours. Take your time. The audience will wait.
I learned the silence move from a stage director, not a journalist. He had us run a scene and then refuse to give us the next note for ninety seconds. Ninety seconds of silence in a rehearsal room is a long time. By second sixty we had figured out the answer ourselves. He never had to give the note.
What 800 of these gives you
Eight hundred is enough that you stop being nervous and start being curious.
You stop preparing your follow-up while the guest is talking, because you have heard the shape of the answer enough times to trust it. You start hearing the line under the line. The complaint that is also a confession. The praise that is also a worry. The pivot the guest doesn’t know they just made. You stop trying to be the smartest person in the room and you start trying to be the one paying the closest attention.
The model is faster than you. The model can transcribe and summarize and route and tag. The model cannot look at a person and decide that the question they almost asked, but didn’t, is the one worth following up on. That is still the operator’s job. After eight hundred interviews, that is the part I am most sure of.
Speaking topics are a list of subjects. The work is the same regardless of subject. Get to minute eleven. Ask the second version. Take the silence. Listen for the line under the line.
Cheers.