The Art of the Interview

Why I Love to do Interviews

AI can transcribe a conversation, but it can’t read a room. Here is how I get past the corporate script to find the “golden” story.

I love interviewing. After all these years, each Zoom invite still feels like a wild card — an opportunity to discover what makes someone tick.

Every person requires a different approach. Some are garrulous CEOs paid to be charming (consistently among the nicest people I speak to). Others are IT directors or project managers with a million demands on their time who are decidedly not happy to be on the phone with me. Then there are the nervous customers and the scrupulously neutral vendors.

I always start with a framework of questions, but it’s a rare conversation that stays on the agenda. Here is how I set the stage for an exchange that actually matters.

1. The “Permission to Relax”

No matter the subject, I find a way to give my subject permission to relax in the first few minutes. I assure them they are free to take the conversation in any direction they wish — this puts their mind at ease if they did not find my questions compelling.

This is the de-escalation phase. My goal is to move from “Subject and Reporter” to “Two experts having a drink at The Columns.” Once that shield is down, the real work begins.

2. The “Disarming Statement”

After the preliminaries, I make a small, disarming statement and watch how they react.

The trick is to move beyond random small talk. If it’s Monday morning and they mention skiing in Chamonix, I don’t ask about the snow conditions; I ask about their favorite spot for apres-ski. More often, it’s a reaction to something they’ve said, just slightly twisted. If they mention an AI pilot project that never got off the ground (most don’t), I’ll say: “Yes, it seems so many people in your shoes are not getting the return you expected.” In that moment, I’m watching for the shift. That validation is the bridge across the trust gap.

3. Picking Words Out of the Air

An LLM can follow a transcript, but it can’t hear the moment someone says something “golden.” I’ve trained my ears to listen for the subtextual shift — the change in tone when a subject hits on something they actually care about (as opposed to what’s on the agenda).

After all these years, I can almost pick those words out of the air. I start to shape the piece on the fly, adding new questions in real time as I see where the human pulse of the story is going.

The Reality

As the industry moves toward “fully automated content” (a sobering prospect) the raw material of that content — the human interview — becomes the most important part of the process. You can't automate trust, and you can't simulate a real connection.

This is not to say I have never had an interview go down in flames. One of my first major feature stories for PC Week happened right at the start of client/server computing. I had an interview in which I faithfully typed down everything the expert said. Unfortunately, I did not understand one word. Then, I got off the phone as quickly as possible and moved to a different source with my tail between my legs. Now, I would have said, “Sorry, would you mind walking me through that again?” Valuable lesson that day: Pretending to understand is a huge rookie mistake.

That early lesson in honesty — never pretending I understand — is exactly what allows me to navigate challenging topics today. With a situation where everyone from industry players and analysts to recruiters and candidates are filling my inbox but staying silent in the comments, the golden story isn't in the official statement. It’s in the pause after I ask a disarming question. It’s in the subtext of what they aren’t allowed to say on the record.

AI can transcribe the words, but it can’t navigate the tension of a difficult conversation. It can’t feel the weight of a topic that everyone is watching but no one is talking about. That is why I still love the interview: because that’s where the truth usually hides.