How to conduct a great podcast interview

One fear that many people have when starting an interview-based podcast is their ability to actually conduct the interviews.

Often, this fear of being a "bad interviewer" is a mental barrier that the host has to break through because, in reality, they would be great if they just gave it a shot. We see this all the time with potential customers at Content Allies.

Regardless, after 130+ interviews on my Working Without Pants Podcast, I've picked up quite a few tips on how to conduct a great interview.

In this article, I am going to dive into those tips and suggest some tactics that will turn even an absolute beginner into an interviewing pro.


Interviewing is easy

One misconception that I must first address is that interviewing people is hard.

To be honest, it's really easy. The guest is going to do 90% of the talking while you sit there and listen.

It's actually much harder to be a guest on a podcast interview than it is to interview someone else.

If you take a few simple actions to prepare for your interview, then you are going to find it super easy and have no trouble pulling amazing insights out of your guests.


Do your research ahead of time

The single most important thing you can do to conduct a great interview is researching your guests. If you show up to an interview and hardly know anything about who you are about to interview, then your questions will be surface-level.

Research allows you to learn those surface-level details ahead of time. This enables you to dive deeper into meatier questions during the interview itself.

But how far do you go with research?
How much time should you dedicate to this?

This varies and is all up to personal preference.

As a bare minimum for research:

  • Spend some time on the guest's website

  • Review their Linkedin profile and career path

  • Try to consume at least 1-3 pieces of content from them (articles, videos, etc.)

This shouldn't take more than 15-30 minutes in most cases to prepare for a basic interview.

In some cases, you may go deeper if there is a guest that really excites you (or if you are an overachiever).

Advanced research for guests includes:

  • Finding other podcasts or places they have appeared

  • Reading the guest's book

  • Listening to full presentations or videos from the guest

  • Consuming 4-10 pieces of content from the guest

Doing advanced research for every single guest would easily become overwhelming. While it does make for a better interview, I typically reserve this level of research for guests who I am super excited about.

Shortcut your research by interviewing those who you already follow:
An easy path to in-depth research is to interview people whose content you are already consuming.

A great example of this is my interview with Mike Michalowicz. I'm a fan of Mike so I had already read 3 of his books, listened to his podcast, and been on his email list for years prior to the interview.

Trying to prep for this particular level-of-depth for Mike's interview would be impossible. But by choosing a guest who I was already a fan of, this enabled me to conduct a great interview because I was already his follower.


Preparing talking points for the interview

One thing that many people do wrong when they start interviewing is trying to list a series of questions and exact topics that they will hit.

Instead of allowing spontaneity to happen, they try to script out the interview like it's a monologue.

The truth is that with any interview, the guest could end up being a wild card and could go off in any direction.

Instead of fighting that, embrace it.

So when you prepare, jot down a handful of questions or talking points that you would specifically like to ask that guest.

But don't go too deep on this. Once you get into the actual interview, a lot of this may just go right out the window. It's good to have as a reference though. You can turn to it if the interview comes to a natural close on a specific topic and you want to dive into something new.

Before each interview, I typically prepare:

  • 2-5 questions or topics that I would like to discuss with the guest


Go where your curiosity takes you

Some podcasts are super structured with their show formats. They ask every single guest the same questions in the same flow.

While a few big-name shows may have made this work, in most cases it feels forced and unnatural.

Instead, what makes for a great interview is to follow your curiosity.

Think about bringing a guest on your show as the chance to sit down and ask a very smart person all of the questions you would love to ask them in a private consultation.

Ask them about their story.
Ask them about how they accomplished what they have.
Ask them to dive deeper on explaining their frameworks or beliefs.
Ask them the nitty-gritty questions that you've always wanted to know the answer to.

When you follow your curiosity, you will naturally conduct a great interview because you are genuinely going to be learning and pulling things out of the guest that you want to learn.

And if you are learning from the guest, then your audience will too.

For example, I received several compliments on my recent interview with Lacy Boggs Renner. Some of my listeners said it was my best yet. Yet I prepared no more for this episode than I did with others.

Instead, I simply chased my curiosity. Early on in the interview, Lacy said, "I've only worked on my business for 20 hours per week for the past 7 years."

That caught my curiosity so I dove deep in on that. I wanted to learn how she has built such a successful business while limiting her hours. I wanted to know what trade-offs she made and how that caused her to approach things differently.

Go where your curiosity takes you. It's the #1 secret to an incredible interview.


How to ask great follow-up questions

If there is one "skill" to develop in interviewing, it would be the ability to ask good follow-up questions. For many people, this comes naturally. If you treat your interview like a conversation, then you are going to naturally ask whatever piques your curiosity next.

But for some people, they may find this hard. They struggle to listen to the guest and then to prepare a follow-up question at the same time.

Here is a simple psychology trick that will help you with follow-up questions. (Ironically, I learned this during a podcast interview I did with Say Gabriel.)

Using active listening to prepare for follow-up questions:
When you ask a guest a question, they are most likely going to talk for about 1-5 minutes before tossing the conversation back to you.

During that time, it is tempting to zone out and just think about your next question prepared. That is a path to a less ideal interview as it won't flow naturally.

Instead, focus on actually listening to the guest. Put 100% of your mental energy into just listening to what they are saying.

Then, if something stands out to you that you want to dive deeper on, think in your brain to say, "One - Let's revisit the topic of ____."

For me, it helps to physically point out one finger and set it down on my leg off-camera.

Then, if a second topic comes up that I want to ask further on, I think to myself, "Two - Let's revisit topic ____"

This all happens mentally while I am listening to the guest. By putting a number to each point I want to follow up on, it makes it easy for me to remember what I wanted to circle back around on.

This prevents that awkward moment where you go, "Oh, I had something I wanted to say but forgot."

Normally, I will max out at 2, maybe 3, topics to revisit during any specific segment of the interview. And by that time, the guest will flip the conversation back to me.

Now, I am prepared with an amazing follow-up question that dives deeper on something they just discussed.

Listen to my interview with Say if you want to get into the weeds on this. It's a subtle mental tactic but it's massively helpful for conducting great interviews.

Active listening is also just an incredible skill that will help you in all aspects of life.

Prepare your intro and outro


The final thing you want to do to prepare for an interview is to have a good intro and outro. This will help you open and close confidently.

For an opener, you can get creative with this or keep it basic.

My general opening flow for the Working Without Pants show is:

  • Ask the guest, "Are you wearing pants right now?" (It's ridiculous but makes for a fun start to every interview.)

  • Banter for 1-4 minutes about work/life balance

  • Ask the person, "For all of the listeners who don't know who you are or what you do, can you give us a quick overview?"

That is pretty much how I open every single show.

Then for the outro, I wrap up in a similar way.

"Thank you for taking the time today. For everyone who wants to find out more about you online, where can they go to look?"

Both the intro and outro are simple and straightforward. I don't change them much as they have become a routine that I can always fall back to with confidence since I know it will lead to a strong opening and close.


Interviewing is just a conversation

The biggest thing I have to remind anyone who is getting into this is that it's just a conversation.

When you realize that you are not trying to be the next Howard Stern, it takes a lot of pressure off.

Instead, you can just focus on having a genuine conversation and letting it flow where your curiosity takes you.

If you follow your curiosity, then you will learn from the interviews.
If you learn from the interviews, so will your listeners.

It's that simple. Don't make it harder than it needs to be.

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