The Art of Being a Great Interviewer (or How Howard Stern can improve your podcast)

Like every great performance artist, great interviewers make the interview look easy. Unfortunately, the apparent ease of what they do encourages too many unskilled and unimaginative sorts to start their own interview podcasts. (At last count, I heard there were more than 250,000 of them. And that’s just in English. Worldwide, there could be millions.)

Doing an interview podcast makes a lot of sense when you are starting out to establish yourself in your field. You need only a few hundred dollars’ worth of equipment and a list of people that have agreed to talk to you for some length of time.

If your interview subject is an expert in your field or has accomplished something impressive, the interview itself – you’d think – would be a good one. Your audience, having subscribed to your podcast because of a shared interest in that field should be captivated by what he says.

But the fact is that most interviews with experts are deadly dull.

Why so dull?

I believe it is because the interviewers ask the same obvious questions the expert has been asked over and over again. So what you get are answers that he has given at every previous interview. He himself is tired of saying the same things, and that fatigue is evident.

Some podcasts are dedicated to celebrity interviews – with movie stars or professional athletes or well-known gurus. You’d think that these interviews would be automatically interesting. But, again, most of them are not. Still, fans are usually willing to wade through the stuff they’ve heard again and again in hopes of catching the rare statement that is new and fresh and allows them to know this fantasy person a little better.

Political interviews? They are even worse than expert and celebrity interviews. You know ahead of time that the questions will almost never be answered directly. What you get instead are prefabricated comments whose only purpose is to sell whatever idea the politician is selling that day.

There are exceptions. There are a handful of people that know how to make an interview come alive.

I’m thinking of Howard Stern, in particular, which may surprise you. If you don’t listen to his show, you probably assume he’s still the shock jock he was 20 years ago. But he’s matured in many ways and has become very skillful.

More about Howard Stern – and how he does what he does – in a minute. But first, let me tell you why I’ve never done a podcast…

When I was writing Early to Rise, I had a large readership – almost a million people at one time. Because of the size of that audience, podcasting would have made good sense. And I was urged to do it many times.

But I knew that in order to draw attention to my podcast in the sea of other podcasts, it would have to be both good and distinct. I had some ideas about how to make it distinct. But the “good” part meant a serious commitment of time.

For every minute of taped podcast, I figured I’d have to put in at least four minutes of research. This meant that a weekly hour-long podcast would require four hours of research plus two or three hours of actual recording and another hour or so of editing. The equivalent of an entire 8- to 10-hour day.

So I backed away. And every time someone suggests that I do a podcast, I remind myself: “If you aren’t willing to do the work, the product – your product – will be shit.”

This brings us back to Howard Stern.

Despite how casual his demeanor and spontaneous his remarks seem to be, his interviews are evidently the result of a great deal of preparation.

Keep in mind that Howard’s been in the radio business for more than 40 years. He began interviewing celebrities maybe 30 years ago. For the first 10 years or so he didn’t do many interviews because people refused to be on his show. And with good reason. His interviews back then were primarily about embarrassing the guest.

It wasn’t a smart political move. It was a very dumb business strategy. Most importantly, it wasn’t funny.

Over the years, he’s taken a different approach. Now, it seems to be about getting his guests to talk more openly and freely about themselves than they have ever done in public before.

And his interviews are very, very good. IMO, Howard Stern is light years ahead of late-night hosts like Jimmy Kimmel, better than syndicated pros like Larry King, and equal to the great Charlie Rose.

I’ve noticed certain things that he does so consistently I’d call them conscious interviewing techniques:

  1. The introduction is always a compliment of some kind. Howard expresses his pleasure in seeing the celebrity by saying something simple. (Even though he may have said the same thing a hundred times before to other guests.) “Well, look at who’s here, looking all thin and beautiful,” he might say, “the great [NAME]…”
  2. He begins with softball. His first question appears to be inconsequential. Like: “How’s life treating you my friend?” I don’t think this is Howard being lazy. I think he does it to make the celebrity feel safe. Taken together, his enthusiastic, laudatory greeting followed by a quick, easy-to-answer question works like a one-two punch. It puts the celebrity at ease, which is exactly what you want at the beginning of an interview.
  3. Next, Howard asks a puerile question. Some version of, “So how great is it to be rich and famous?” Usually it takes the form of, “So how much action are you getting?” Followed closely by, “Did you ever think you’d have sex this good?” (Contrary to what many believe, I don’t think for a moment that he is the least bit interested in the answer.)

James Altucher, who happens to be one of the best podcast interviewers I know of, told me something that may have a bearing on this subject.

Lately, he’s been trying to learn the very complex skill of stand-up comedy. And he said that the most important lesson he’s learned – more important than writing and delivering funny jokes – is that you have to make the audience like you.

I was surprised to hear that. It sounded wrong. But when I thought about my favorite comedians, I realized that I liked them all. Even those whose mannerisms or language or attitudes – or even humor – I didn’t like or disapproved of. I’m thinking of Rodney Dangerfield… and Howard Stern.


William Zinsser on the Art of the Interview

William Zinsser was an American writer, editor, literary critic, and teacher. He had a long and distinguished career writing for the New York Herald Tribune, as well as many national magazines. He also served as executive editor of the Book of the Month Club from 1979 to 1987. His books include the classic On Writing Well. The American Scholar website ran his weekly posting, “Zinsser on Friday,” featuring short essays on writing, the arts, and popular culture.

Here’s what he said about how to conduct – and write – great interviews:

Get people talking. Learn to ask questions that will elicit answers about what is most interesting or vivid in their lives. Nothing so animates writing as someone telling what he thinks or what he does – in his own words. His own words will always be better than your words even if you are the most elegant stylist in the land. They carry the inflection of his speaking voice and the idiosyncrasies of his conversation and the lingo of his trade. They convey his enthusiasms. This is a person talking to the reader directly, not through the filter of a writer. As soon as a writer steps in, everyone else’s experience becomes secondhand.


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