Speaking of: Howard Stern

Howard Stern will never not blow me away as an interviewer. Every time I've watched or listened to one of his interviews, with literally no exceptions, I've walked away feeling like I've learned something truly inspiring, revealing, or just plain interesting about the interviewee's life. Watching him work reminds me how much of a craft and art form interviewing truly is.

By today's streaming numbers, the most popular interviewer on the planet is probably Joe Rogan, as much as saying that makes me want to inject myself with horse dewormer. Rogan's style is extremely laissez-faire; he sits back, asks a question, lets the discussion lazily drift for a half hour, changes the topic from one government conspiracy to the next, and just sort of winds up the conversation and lets it go on and on and on knowing his fans will eat it up either way. Maybe I'm being too cynical here, but I just never see much of a skill to what he does outside of him just being able to hold a lazy three hour conversation with anyone on the planet (which is admittedly impressive in itself).

Howard Stern is the polar opposite. Howard does his research. Howard knows details about that person's life that no one has ever asked about before. Howard has a carefully constructed roadmap of where he wants to steer the conversation, and it seems like he executes nearly every time. He's not afraid to ask hard questions. He's not afraid to ask vulgar questions. But I don't think guests are as open on any other show on any other platform than they are on his show. I think part of this is because of his relatively spontaneous and wild personality on radio; it's comforting knowing that no matter what you answer in an interview, Howard will likely say something crazier during casual radio banter within the hour. But more than that, I think people can genuinely sense the work he puts into his research before an interview, and as a result, they don't feel like they have to bore Howard with surface-level details about their life. Howard already knows these. It's a free pass to cut right to the bone.

I can understand how some people who prefer the more laissez-faire approach think Howard butts in too much while his guests are talking or pushes forward his own theories concerning that person's life too often, but I think both of these components are actually critical to his success in getting guests to open up. First, by butting into the conversation, he can steer it with a surgeon's precision. But also, by being unafraid to give his own predictions on how someone is going to answer a question — explaining what he thinks a songwriter wrote a song about, for example — he's also approaching the topic from a completely different angle. To stick with the previous example, songwriters are asked all the time, "What did you write this song about?" But they're rarely asked, "To me, this song is you singing about x, x, and x. Am I wrong?" It's the same question in spirit, and this tactic can often come off like him trying to put words into his guest's mouth. But every time he does this, you can see the guest's talking points fly right out the studio window. It's a fresh perspective on the question, and I think guests enjoy digging into this.

He just makes everyone feel so comfortable speaking about anything, and you can visibly see it on people's faces when they're in his studio. It's a beautiful thing, really. What an incredible skill he has honed.