Better Interviewing: Part 1, Winging It

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Winging It

To make a memorable interview podcast there’s no escaping preparation.


Stand-up comedy is simple. It’s just you, a microphone and an audience. Interviewing is pretty much the same deal with an additional person. Though, in stand-up the aim is to make people laugh, in an interview it’s to make them care.

There are a number of potential pitfalls on the road to making people care. The big one is a lack of preparation. Winging it is a popular, shall we say, “stylistic choice” in podcasting. Many online media presenters rationalize it makes interviews authentic, which is what the audience supposedly wants. Moreover, why spend hours researching your guest beforehand when you can just wait until you meet with them, hit the record button, and ask for the information then and there? Voilà, that’s a show.

However, the interviewer who pulls questions from you-know-where has as much chance of making people care as a stand-up comic has in making people laugh by taking the stage with no material, trying to think up new jokes in front of a crowd. A good comic can deliver a stand-up routine over and over, and each time make it sound fresh and funny.

When it comes to interviews, for instance, Howard Stern sounds ad libbed. Yet he hits the right notes. When Stern often tells guests, “Here’s one thing I wanted to ask you,” it isn’t a question that occurred to him in the shower last year. He and his producers mapped it out beforehand. If you want to do an interview that moves people, you don’t want to make it up on the fly. You need to plan and conduct the interview as if it isn’t planned.

This was well understood before podcasting arrived in 2005. Show development, research, and planning were standard practices in radio and television. But podcasting shook things up. You no longer needed studios, transmitters, and satellites to produce a show. Nor did you need collaborators or editors. Recording equipment was cheap and distribution was free. To the podcasting community this was more than just a technological shift. It was power to the people, throwing old media and its practices over the ship of modernity into the waters of oblivion—or so they thought. There were a lot of godawful podcasts back then.

Today the medium is starting to mature. Winging it is still a popular approach but more novice producers are embracing tried and true production principles that address how to attract and serve an audience. And broadcast professionals are entering the space as advertising grows. Still, podcasting is wide open for anyone with a passion for a subject, a $99 recorder and an iTunes account.

How do you rise above the noise? How do you take an interview show beyond vanity project or infomercial to really build an audience? If you’re serious about making shows that move people, it requires an understanding that interviewing is essentially show biz.

What Is An Interview?

Asking questions and getting answers happens in the interaction between an interviewer and interviewee. But that in itself is not compelling. The mistake is to approach it as if it is; as if people are attracted to the information and the interview is necessary to gather the data.

That’s not what gets the attention of an audience.

People don’t tune in to The Tonight Show to acquire information extracted from a guest. If that were the case, it would be easier and cheaper to forego the cameras and crew, email the questions to the guest and just publish their reply. So, why do people watch The Tonight Show?

They’re drawn to the theatrical performance of Jimmy Fallon and his guests. All of the great interviewers put on a show every time they open the mic: Charlie Rose, Larry King, Terry Gross, et. al. Their programs have beginnings, middles and ends. They bring out the drama in what their guests have to say. They tell stories.

The dictionary definitions of interview are fine for everyday use: “a meeting at which information is obtained from a person.” This definition covers many kinds of interviews from journalists gathering comments and sound for their news reports to employers talking with job applicants. In this article I’m only concerned with the interview as a show presented to an audience. I find the definition below more effectively captures its dynamics.

An interview is a stationary two-person nonfiction play of impromptu dialogue directed by the interviewer.

It’s a weighty description but over the next several articles we’ll dissect it and hopefully give you visibility on how you can achieve it in your podcast or interview show.

The Play’s the Thing

An interview’s capacity to attract and hold an audience comes down to human empathy. In this regard there is a format that reigns supreme: the story.

Why a story is so effective at conveying information is a vast subject. As early as Aristotle, philosophers delved deeply into the power of storytelling. The historian Yuval Harari asserts all human thought from the hunter and gatherer stage until now is a narrative, whether it’s the politics of nations or something as mundane as putting on a shoe. He famously describes therapy as an attempt to stop believing one story about ourselves and start believing another.

People crave stories. Jack Valenti (former president of the Motion Picture Association of America), when appearing on panels at media and tech conferences during the height of the Napster controversy, argued numerous times that stories are so vital to human existence more people steal movies than steal money. There’s no hard evidence to prove it, but it’s difficult to argue stories are anything but a primary element of our society given the presence of news, television, radio, movies, music and social media in our lives.

Formal story structure has changed little, if at all, over thousands of years. It’s comprised of at least three elements: [1] exposition, the introduction to the character and the events leading up to his or her challenge; [2] conflict, the challenge itself; and [3] resolution, the character meeting the challenge.

Stories are always about people. Stories happen to people, but never to objects, ideas or products. An object can be in a story. An idea can be the meaning of a story. But objects and ideas cannot become, nor face a challenge and meet it. People can.

I’m not suggesting a compelling interview needs to contain spectacular stories of thunderous drama. No, the issue is telling a story versus merely delivering information. Take company podcast interviews for example. They tend to be so dreadfully boring because they lack conflict. The marketer’s knee-jerk wisdom is people will like the company more if everything is perfectly in place. But we all know, if anything, the opposite is true. No one is drawn to a saccharine interview. In fact, many are repelled.

Like a squirrel to a dog, so is a story to an audience. It gets our attention. Conflict and how a person deals with it—no matter how trivial—formatted as a story appeals to human instinct.

Your quest as an interviewer is to find your subject’s stories. If the interview is 30 minutes long does that mean 15 minutes of exposition, 10 minutes of conflict and 5 minutes of resolution? Maybe, if you’ve set down a good plan. But a good interview is generally made up of many small stories, some of them lasting a few minutes.

Your guest probably won’t be thinking in terms of stories but you will. Suppose you’re interviewing a runner who’s excited about winning $100 million, buying a beautiful home on a private island, amassing a world class wine collection, driving a Bentley and enjoying a gig as a spokesperson for Rolex. They mention an arduous 100 mile run they had to do through the Himalayas up and down treacherous roads where they almost died.

Do we care about what it’s like to ride in a Bentley? Probably not. It’s interesting for possibly just a sentence or two. But as an interviewer the treacherous roads are your stock in trade. If you look for them in what your guest says they are everywhere. And once you see them, they become the foundation of the story structures of your interview.

The story is what gets your audience to care. Hamlet knew this when he hatched his idea to write a play so devastating to the senses, upon seeing it his stepfather would involuntarily reveal his guilt over the murder of Hamlet’s father. Hamlet predicts:

“The play’s the thing, wherein I’ll catch the conscience of the King.”