When I first started podcasting in 2006, I didn’t possess the technology to do interviews, so I left that out of my show for a long time. One of the first interviews I did in 2008 was with a gentleman named George Tabb, a NY punk icon and early activist for those who suffered from 9/11-related sickness. While it was a bit stilted and awkward, it gave me a definite idea of the kinds of interviews I wanted to do in the future.

I think the essence of a good interview is that it isn’t an interview at all. It’s a conversation. That’s why Larry King and Howard Stern are so good at their job. They engaged in a conversation with their guests, and in doing so, they could draw more out of their guests than intended. Someone who has appeared on Stern has said they told him things they would never have spoken to anyone else. I think that’s a high compliment, and it’s certainly something I try to emulate. Last year, I did a limited series of interviews on my podcast related to how people became creatives and how they stayed creative during the pandemic. I’m biased, but I think it’s some of my best work because I think I managed to get into a personal zone with people and gain their trust during the process.

I am by no means an expert, but I do know what works for me. So I’d like to share with you five things I would do when interviewing guests.

Do your homework

If your guest has written or appeared in anything recently, you need to know about it. Read and consume anything relevant to your conversation, and maybe go beyond that. I like to ask relevant questions, but I also look for human moments in a person’s bio, social media, blog posts, and videos. If it’s funny, all the better.

Now, you may want to tell the guest you found this moment and ask if it’s ok to bring it up. Don’t go for embarrassing the guest. It’s crass, and that guest has friends who will hear about it and never appear on your show. In my experience, the human moments we all share can be a real icebreaker or pressure release during an interview. If you can get the guest to share that laugh with you, you’ve got a good conversation going.

Listen. Really.

It’s easy to get sidetracked doing other things while the guest is talking. Riding a volume level, responding to chat if this is a live stream, posting quotes on social media, and other things. I’m asking you to stop that. Your focus should be entirely on the guest and what they are saying. I have heard my share of podcasts where The host prepared the questions well in advance, and the guest said something nullified a question, only to have that question pop up later in the show. That’s an unforced error, and you’ll pay for it. The other problem with not focusing on the guest is that it becomes very awkward. Sure, you can fix long pauses between questions in Post, but the guest may have a bad feeling about it, and it will reflect in their attitude, and the quality of their performance as the interview goes on. If you realized the person you were talking to wasn’t paying attention, how long would you stick around and participate? Exactly.

Be prepared to go off the list

I want to be clear about this point. I am not saying that you shouldn’t have a list of questions or a game plan for this interview. I am saying that if you’re actively listening to the guest, they may say something that opens up a whole new line of questions you hadn’t thought about and might be worth exploring. Conversations are not linear; you can drop one thread, pull on another one for a minute, then come back to the first one. That is what makes for an organic, authentic experience for the guest and the listener. If the guest feels you are in this experience with them, chances are they’ll trust you more, and they’ll loosen up and give you the interview you want

Stay in tune with the guest

You should be getting a good read on your guest as the interview proceeds, and you should be getting an idea of places you should and shouldn’t go. If you inadvertently head down a path the guest doesn’t want to go, and they might clam up a bit, don’t push. In some cases, the guest might say something they didn’t realize would take them down that path and then give you some indication that they’d rather not. If you hit a boundary, respect it.

Know when to end it

Ideally, you’re looking for an interview to take up a substantial part of your regular podcast, but like any party, you should be looking for hints that the party is ending. The guest might start giving you shorter answers or other context clues when they start feeling like they’ve said everything they need to say. When I get to that point, I have two questions I ask to signal the guest I’m starting to wrap up. I’ll ask what they’re working on now (or next) and how people can connect with them on social media. Then I’ll thank them and wrap it up. Know when that time is coming, and don’t stretch it out. An interview that goes too long becomes awkward later, and the listeners will pick up on it.

Interviews don’t have to sound like interviews; they can be all call and response and no substance. To get to something real, don’t treat it like an interview. Treat it like you’re just talking to a new friend you want to get to know. The result is a better product for you, a better experience for the guest, and trust as an interviewer grows in your field.