When I started the Loose Threads Podcast, the goal was to have real conversations with real people who were working across the consumer economy. I use the word “real” twice since I wanted to give people the space to honestly tell their story in their own words. I wasn’t going to cut the show into 30 second sound bytes and string a grand narrative around it with voice over. I wasn’t going to let people give their rehearsed pitch for ten minutes and then call it a day.

I was just going to have a conversation with an interesting person that we would record and release to the world. Even so, I was not trying to trap anyone with trick questions or extract private information from them. How could I preserve and channel a guest’s honesty while making him or her very comfortable during the interview? I had to find a new approach, and it’s one I have honed over the last fifty episodes.

Since my somewhat unorthodox approach has worked, people are increasingly asking how I make the podcast what it is. While there are plenty of good guides out there about how to handle the technical side of a podcast or recorded interview, there is much less information about how to actually interview people in a way that captures as much of their true self as they are willing to share. Full truth is nearly impossible—nor desired maybe—but I want to capture something right below what one would share with his or her therapist, if this therapist had a fascination with business, operations and strategy.

Because I had no track record as an interviewer when I started the podcast, I got the first two dozen guests either through friends, introductions or cold emailing people. But since then, as the Podcast’s reputation has grown, people have started reaching out directly, pitching themselves and their clients. While it’s exciting that the roles have flipped, it also presents a range of new challenges for dealing with PR.

As we increasingly live in a world where little mistakes can quickly turn into big mistakes, I understand the need for people to surround themselves with PR people who ensure everything is on message. But this has made the interviewer’s job much harder, especially when one wants to cover new ground that is rooted in honesty and truth. Given this reality, I am continually evolving my interviewing process, which tries to get to the core as quickly as possible and cut out the noise.

This same mentality also applies for moderating panels or fireside chats. This approach is arguably more important for a live event, since everyone on the panel wants to look good, as do the people organizing the event. Everyone often wants to put so many boundaries around interviews that nothing unexpected can happen. Yet this uncertainty—what I call respectful uncertainty—is exactly what makes an interview good.

Before diving in, it’s important to mention that this is my approach. It works for me but might not work for everyone.

Before the interview

  • Do not send any questions in advance or allow the guest to prepare anything for the interview. A good interview is inversely correlated with how much someone is able to prepare for it. People that are comfortable talking about what they do and have something to say are always the best guests. They don’t need preparation.
  • If someone insists you send questions in advance, put a few together that you don’t feel strongly about. Just know that you will not ask these questions during the interview. This might sound like a trick but it’s necessary and it works.
  • Instead of sending pre-written questions, create a familiar but unpredictable structure for your interviews. If people want to get a sense of the interview, suggest they listen to some previous episodes that reveal the general arc. This allows them to get a sense of your approach without you divulging where you will take the conversation.
  • Always schedule a pre-call before recording the interview. This will give you a sense of how the person talks and thinks. If he or she has trouble putting together sentences without using a lot of “ums” and repeated words, you might need to think about how much of a burden the episode will be to edit. (More on this later.)
  • On the pre-call, do not share any questions with the guest. You can explain your approach but do not share anything that they can really prepare for.

During the interview

  • Do the interview in person. It will sound better and you’re able to build rapport with the guest before and after the interview. Sometimes you can even start recording again if the conversation after the interview is relevant (it often is).
  • Never let a PR rep in the room during the interview—ever. They can travel with the guest if they would like to, but the interview room is a sanctuary that cannot and will not be disturbed. I am adamant about this and will walk away from interviews if the guest or PR rep does not agree.
  • As the interviewer, you should walk into the room knowing a solid amount about the person and their company, but not having researched every possible thing about them. I try and take the perspective of the listener who might not know a lot about the guest and try to use the episode as a learning tool. This ensures you are taking the audience along for the ride and the episode is self contained, so no one needs to do extra research to understand it.
  • Make the interview long enough that the guest has to exhaust all possible PR-rehearsed answers in the first ten minutes of the interview. I record for an hour and end up with a 30-45 minute show.
  • Keep the guest on their toes about where the conversation will go next. The best way to do this is to also keep yourself on your toes about where it will go next. I walk into the interview with no set questions besides three main ones: 1) “Talk a bit about your background;” 2) “Where did the idea for your company come from?”; and 3) “What’s the cheapest and most expensive lesson you’ve learned?” This last one is my personal favorite, which I ask towards the end of the interview. I think of almost every other question on the fly. I just keep a notebook open during the interview and write down questions as I think of them. You want to establish a flow where you can move around a bit but there is still a backbone that keeps the episode moving. For me, that’s using time (as in the person’s and company’s chronology) as an arc for the episode, but allowing us the flexibility to go down different rabbit holes as we see fit.

After the interview

  • The guest is not allowed to hear the episode until after it is released. Always maintain full editorial control over the episode.
  • Make sure the episode keeps moving. If something is dragging, cut it. If something is not relevant, cut it. Even though it’s a long-form interview show, it still needs to move. Don’t be afraid to cut things. Second opinions are helpful here since you might be too close to it.
  • The longer the episode is, the more you need to clean up what are called disfluencies, the things you will listen for during the pre-call. People say “um” and stutter all of the time. It’s natural. However, over time it wears down the listener. We spend the vast majority of our editing time cleaning up these little imperfections, which make the episode flow much more smoothly and also cut anywhere from five to 15 minutes from the episode. The first few episodes of the Podcast were barely edited, and they are not as good as the later ones as a result. This will take time and cost money, but it makes a massive difference. People don’t have a lot of patience for incoherent speakers in long-form interviews.
  • The episode should probably be shorter than you think. I always liked long-form reading and audio, and early episodes were about an hour long. I eventually realized this was too long, since most people listen to podcasts at normal speed, not 1.5x or 2x like I do, and they often listen during commutes. We have adjusted the show to always be between 30-45 minutes per episode, which has been much more successful. This also forces us to cut things that aren’t interesting or essential.

Paradoxically, even though this approach advocates for little advance preparation, it’s a ton of work during the interview to pull it off well. I, as the interviewer, always have to be on, listening intently and figuring out on the fly where to take the conversation next. Yet it is this commitment that makes the interview good for everyone involved. You will walk away with a great conversation and the guest will walk away having thought about things they previously haven’t, in addition to having an opportunity to explain what they do entirely in their own words. This last part is very rare in an age of short soundbites. 

If you’re not tired after interviewing someone for an hour, either it wasn’t a good interview or you prepared too much. If you’re exhausted, you likely just accomplished something very hard: you produced an interview that’s new, engaging and unexpected. What more can you ask more. 

Listen to the Loose Threads Podcast

Thanks to George Drake Jr, our excellent podcast editor, for helping shape a lot of this thinking. I will update this post over time as my own methods evolve. Have questions or ideas? Email me. hello@loosethreads.com