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How Not to Interview (Interesting People)
As a photographer who is primarily a writer, I like reading about photography so I can learn from those who create. I do that by reading photo magazines and listening to podcasts. One such magazine is Aperture. They take me out of the noise and bring me right into the core of the work. Photographers I don’t follow, or don’t know. Always a pleasant surprise.
In a recent issue they ran an interview with Christophe Lemaire and Sarah-Linh Tran. I have followed Lemaire since his time at Hermès, so I was genuinely excited to read about how he and Tran think about creating. Lemaire is one of the few fashion brands that earns the word “philosophy.” These are people who think in multiple planes: fabric, cinema, sociology, memory.
The initial excitement soon turned into disappointment. Not with the subjects but with the actual interview, and more specifically with the person doing the interview. The interviewer, Alistair O’Neill, an academic from Central Saint Martins, was so much more interested in impressing the subjects that he could never get out of the way.
He finished their thoughts or volunteered his own references. He mentioned mid-interview that he had recently interviewed someone else, for a book chapter he is writing. He was, in the politest possible terms, more interested in being seen conversing with interesting people than in what those people actually had to say.
This is the interaction I see everywhere. The mutual admiration interview is a genre of its own. You see it in podcasts, in magazine profiles, in the long-form Q&As that cultural institutions produce to signal seriousness. The subject is interesting. The interviewer is credentialed. They agree with each other at length. Nothing is at stake. No one is surprised. You finish reading and feel vaguely full but can’t say what you ate. It is worse on technology podcasts. You know people are doing interviews to accumulate symbolic capital, not insight.
Everything gets so diluted that you lose the actual substance. The comfortable questions. Nothing proactive or one that scratches the veneer. The best interviews I read were in Rolling Stone, Creem, and Spin magazines. The interviewer didn’t guarantee to agree. Not hostile, or antagonistic. Not adversarial in the cable news sense. Just genuinely curious enough to risk the awkward follow-up. To leave a silence instead of filling it with your own reference.
Lemaire said something worth sitting with: “Style has a kind of mystery about it. You see someone in the street passing, and you’re like, who is this person?” O’Neill nodded and moved on to Irving Penn.
This was the heart of the conversation. The real reason for the interview. Sitting in that sentence. Pulling on it. Why does mystery matter? What does it mean to make clothes that resist easy categorization in an era when everything is optimized for instant recognition? What does that cost commercially? How do you survive it?
Instead: Penn.
FFS!
Five Things Not To Do
- Finish their sentences. You are not the subject. They are. So let them lead. Otherwise you get the answer you expected, not the one that was coming.
- Volunteer your own references. Every time you name-drop, you redirect the conversation back through yourself. The subject stops leading. You get zero revelation.
- Mention your other work. Nobody you are interviewing cares about your other work. Unless they specifically ask or comment about it, it just gets in the way.
- Ask only comfortable questions. Agreement is not a conversation. It is applause. The interesting stuff lives precisely where the conversation gets uncomfortable.
- Fill the silence. Silence is the ultimate pressure. Pressure produces truth. The instinct to rescue the subject from a pause is the interviewer protecting themselves, not the reader.
What Rolling Stone Interviewers Got Right
The Rolling Stone interview has shaped my approach more than any other style. The long, languid, and learned approach is still my cheat sheet. The contrast with today’s technology podcasts could not be starker.
A few things from those interviews that have long since been forgotten, but I often use as part of my interview toolkit:
Take your time. An interview is not a two-hour session. You need to spend time to learn about your subject. When I met Brunello Cucinelli, I had no plans for an interview. It was a 30-minute meeting. It turned into a day with the man. It is still one of my most well-read interviews. And I have been a professional writer for the best part of four decades. If you saw the movie Almost Famous, the main character based on Cameron Crowe didn’t get just one hour in a hotel room. He got days on a tour bus. Proximity produces honesty. The subject stops performing eventually. But of course, you could be Lex Fridman. You could talk, and talk, for hours and numb your subjects, not to mention atrophy the brains of your listeners who actually listen.
Do the research. It is really important to know your subject’s work. And how they think. The Rolling Stone writers were music fans, but they were experts as well. They knew music, they knew the backstory, and they just had knowledge. Not just prepared questions. That knowledge meant subjects couldn’t hide behind vague eloquence. Charlie Rose did good interviews on television. Whatever you thought, or still think, of him, and there is plenty to think about, he arrived at every interview with what felt like a Ph.D. in his subject. Politicians, novelists, scientists, filmmakers: with the help of his team, he knew how to guide the conversation no matter what. His work and Rose the man are two different things. The lesson survives him.
Follow the contradiction. I recently wrote about the ever-changing arguments of Sam Altman around advertising. It is not unfair to ask him directly: what happened? Why did you change your thinking? When a subject says something that doesn’t square with what they’ve done or said before, pull on that thread. Politely. Persistently. It is an opportunity to explain for the subject, and for readers to learn. Your role as an interviewer is to bring an understanding about the subject to the reader. You are only interesting, and what you know or say is interesting, only if you are able to achieve that.
Let them be uncomfortable. You have to read the John Lennon interviews in Rolling Stone. They are hard to read. That’s the point. Nobody rescued him from the difficult moments. The reader deserved that discomfort. So did Lennon. Comfort is the enemy of truth in any conversation worth having.
Be present, not prominent. I go into every interview curious. I want to come out smarter than when I walked in. And the only way to do that is to listen. Really listen. You feel the great interviewers in the room. You never feel them performing for the room. That difference is everything.
A Report Card Of My Own Work
I am not going to say that I am good at following my own rules. I slip up, but with the right intentions. I have linked to three long-form interviews with Brunello Cucinelli, musician Nitin Sawhney, and writer and culture critic Jenna Wortham. In these interviews you will find moments where I insert myself.
I make a verbose speech with Nitin, and with Brunello I talk about myself more than I should. But if you read the interviews, there is a reason for breaking the rules. I am not trying to get off the hook. What I am trying to point out is that whenever I have inserted myself, it is because I am hoping to unlock and provoke a response. I use this technique not to be antagonistic, but to share my own foibles.
To push, to provoke, to offer a thought they can agree or disagree with. The conversation, at least for me, moves forward. When O’Neill inserted himself into the Lemaire interview, the conversation folded back on itself. It became about the interviewer’s taste, not the subject’s thinking.
That is the only test worth applying. Who is this serving? If it is the reader (or listener) then you are on the right track.
For what it is worth, here is how the Rolling Stone tests apply to three of my own interviews:
Take your time. The Brunello interview is all about taking the time. A 30-minute meeting that turned into a day.
Know the work cold. I have listened to Nitin Sawhney for years, so it was easy to follow and talk about the emotional and musical evolution of his work, and elicit responses.
Follow the contradiction. With Jenna Wortham, I push on the gap between internet idealism and structural racism directly and persistently.
Let them be uncomfortable. Jenna yes. Brunello, probably not as much. He is a philosopher-king who never gets rattled.
Be present, not prominent. The Nitin nostalgia speech and the Brunello ending are the two places where I cross the line briefly. I know it. Now you do too.
March 19, 2026.
Oh yes this. So much. We also see and hear a lot of journalists interviewing journalists or the moist annoying news anchor interviewing remote reporter.
Well that sadly is the outcome of “filling space” or “filling air” because we have so much of it.
This is awesome. Makes me want to interview someone right now! 🙂
Thank you. I hope you do and do a better job than them professional interviewers!
I’d be curious to hear if you think Stephen Bartlett of The Diary of the CEO is a good interviewer? His reach is phenomenal and he talks about his 1% improvement method with his team.
I occasionally listen to that podcast, as I don’t really like the celebrity CEO conversations. Only a few of his guest interest me.
Outstanding insights here. I’ll want to re-read this and perhaps comment further, but for the moment I’d like to extend your point a little. Every conversation is, to some extent, a mutual interview, and our culture throughout the Anglosphere favours many of the mistakes you call out. We rush to fill silence, we give confident opinions when we haven’t done the tiniest research, and above all we interrupt one another. Not that all interruptions are harmful—those that help the person being interrupted, as to ask for a definition or clarification, or to request that the speaker elaborate on a point too casually passed off, are respectful, productive, essential. Far too often, though, we interrupt to boost our own egos, to imply that we already know what the person interrupted was about to say, to offer snap judgements, or merely to swagger, as by airy dismissal or smug cynicism. With a few honourable exceptions, we could ALL stand to shut our damn mouths and listen more. Selfish Interruption is conversational vandalism.
“Selfish Interruption is conversational vandalism.” Put this on a t-shirt. Because that’s all it is, and we live in this world now.
Thanks for the comment and reading.
I was thinking of an email exchange I had with you that took place maybe a year or so ago as I read your article. I believe that I agree with all of your suggestions for interviews and was thinking about the last time I interviewed anyone. I was kind of satisfied i met your standard with the questions I asked a live sound production engineer on recording artist and sound engineers relationships as far as creative licensing, and live performance royalties. The interview was for a magazine I am trying to start named NIP (Next Intellectual Property). Then I remembered our email and I think I infused myself into the conversation a bit too much to be viewed as a success given your 5 bad practices for interviews. However, as with almost any view or belief, everything is relative, that is to say, shouldn’t we take into account what we are interviewing for? I’ll clarify, I didn’ t have a job nor recieved any funding for my projects when I was reaching out to unknown venture capitalists and companies to support me in what I was creating, the world of VC’s was quite foreign to me and I’m afraid not much has changed, I still have no job and no funding and know that world only better than I did when I first wrote you by some terminology only. I was however desperate to prolonge my involvement with an occupational direction that brings me much joy and I think could do the same for others, so the questions I asked you were laced with a personal agenda, hoping to fleese you into believing i had at least half a brain and maybe even convince you to read my story. I don’t think it worked because you never responded to my reply to your advice on diving deeper into video and forgetting the written word. However, I think it might have been what your article describes as creating a tension filled question. I’ll remind you, it went something like why do you give advice to go for video, and invest in tech companies yet in your personal practice hold onto the still as your artwork? Anyways I enjoyed the read, also would you mind if I put that email dialogue in my magazine?
Hey
Thanks for your comment. Really appreciate it.
My memory has faded on our conversation as it was a while ago, but I would say, I remember it being vigorous.
As far as our email exchange for sharing in your magazine, I would say since it was a private conversation, so let’s keep it private. It won’t make sense or be fair to me to have it out there.
Cal Fussman, who spent years interviewing for Esquire, once said, “Let the silence do the work.” It’s incredible what silence can produce from someone when it’s allowed to do its thing.
Hi, Om! Its been a while that I got a chance to read your article, it’s surprising no photo or picture in the blog that can present the content!
It’s interesting article sir, with lots of information to learn, it is the fundamental information for an interviewer or interviewee! I like the way the information which is presented, it really made my coffee more interesting to drink and start the morning! Cheers!