The 'Art' of the Interview

I‘ve been thinking lately about documenting the processes for doing all of the things that I do. Perhaps doing this would make me better. And maybe a few people would be interested in the results.

My very next thought was, “What processes?”

There is nothing wrong with process. I have many very process-oriented colleagues and they get stuff done. But 'process' has never really been my thing. I have always been a “wing it” person. As a writer, on-stage interviewer, podcaster. All the things I do.

And this lack of a discernible process is most glaringly apparent in how I approach interviews. Yet as I think about it, there is a process there after all.

Wherever a PR person requests a list of questions for an interview I am trying to book, I decline or deflect. I do not cite journalistic ethics when I do this. This seems to annoy anyone who isn’t a journalist. I tell them the truth. And the truth is that I rarely prepare questions. And when I do I never (or rarely) ask them.

Sometimes I say by way of explanation that I think well-prepared, scripted interviews suck. I might put it differently when I say this, but it is what I believe.

Most shrug off my unwillingness to supply questions in advance (it has long been considered an act of professional self-respect to refuse such requests). Sometimes a participant in an upcoming panel discussion (a kind of interview) will insist they need a list of questions to help them prepare.

I generally comply with these requests. Events are a different animal than media interviews. However, I usually add something like, “Be prepared for the likelihood that I will ask none of these questions.”

Occasionally this will freak someone out. Especially someone speaking at a conference for the first time. I get it. But my process (or lack thereof) will never change.

When I deal directly with the subject in setting up an interview or a speaking engagement, they usually roll with my “process”. In my experience, the more handlers are involved in booking a guest or speaker, the more drama there tends to be over things like prepared questions. I am sympathetic. If something goes wrong, they get blamed. But again this is not reason enough for me to change.

Do As I Say, Not as I Do

The last lesson I want anyone to take away from what I have just said is, “If you want to be good at interviewing people, never prepare questions”. That is terrible advice. It's akin to telling a college student to do what they love, not what they are good at.

There are many all-time greats at conducting interviews. And among them, there are a range of approaches to preparation.  Some are meticulous preppers. I suspect more than a few wing it like me. To be clear, Jiminy Glick is not one of the greats. Kara Swisher, the late Mike Wallace, his son Chris, Terry Gross...almost any host on the BBC. The list goes on. They're all great. And all very different.

Of Course, I Prepare

The real truth is that I do prepare for interviews. I read. I talk to people. I listen to previous interviews. And so on. But at most, I jot down a couple of words or phrases that are important to what the interview subject is all about so I don’t forget to bring them up. I still might forget, but this helps. To most people, this looks like winging it. But it is more involved than that. Just not a lot more.

The key to getting away with winging it is to appear buttoned down during the interview. Some people may want to see you sweat. But most don't. This particularly applies when an interview is happening live.

One trick to avoiding trouble is to have a few stock questions to fall back on when needed. For example, whenever I interview an entrepreneur, which I do frequently, I will often ask them, “Tell me about your first business.” It’s a great icebreaker.

And it spins off follow-ups. This is another key to a good question. Does it produce a litter of follow-up questions? And do these follow-ups take you down the right path? Or do they lead to a dead end?

Sometimes the answer to the my-first-business question is an exceedingly precocious invention like "I turned the family toaster into a drone that counts the number of bees in a hive. I then sold the design to an agricultural conglomerate for millions. I was 11 years old."

A more likely answer is an 11-year-old’s notion of arbitrage.

For example, when I recently interviewed the entrepreneur David Shim (founder of Placed and Read AI) at a conference, I asked him this question.

His answer? He bought candy in bulk and sold it to his friends at school. For a profit of course. Real entrepreneurs have stories like this one (or bee-counting toaster drones). The rest of us had lemonade stands.

Interviewing multiple people at once is a different experience than a 1:1 interview.

The Sound of Two People Talking

A good interview isn’t about filling up an agreed amount of time with the sound of two people talking. It isn’t about winding someone up to spit out shop-worn talking points about their new book, startup, or podcast. Whatever they’re selling. It's never about asking them what they want you to ask them.

An interview is about having an interesting conversation with someone. And more to the point, a conversation that either entertains or educates the audience. Ideally both.

In my experience, the more prepared or rehearsed an interview is, the worse it is. The audience is bored. Or they see right through the charade and feel manipulated. And they’re bored.

Your job as the interviewer is to get the subject to say something real. Or unexpected. Or to share something revelatory. About themselves. About their industry. About the inner workings of what they do. The entertainment and education must come from the subject.

This isn’t about you. The best drummers are the ones you don't notice. They just keep the beat. The interviewer's job is similar. The less you are noticed, the better you are doing.

If the interview subject can barely sit in their seat and is telling stories and sharing anecdotes, you’re probably winning. If they are sunk deep in their chair spewing monotonous talking points you’re losing.

Interviewus Interruptus

No one likes the incessant interrupter. We all agree it’s obnoxious. But if you never interrupt your subject – to challenge them, ask for more detail, redirect them – you are not doing your job.

Own the moment. Your best question is rarely the one you wrote down weeks ago.

Your best question is never the one your subject asks you to ask them.

Your best question is usually the one you ask in reaction to something important your subject just said.

On stage.

Live.

With dozens, hundreds, maybe even thousands of people watching you.

So, keep your eyes on your subject. And listen.