Have you ever dissected your favourite podcasts with the goal of figuring out why exactly you like them so much?

You might uncover many aspects that make them stand out to you, some of which we might’ve discussed here before. Some of these are dependent on the format of the show and the subject matter, but seeing as the majority of us run interview style shows, there is one element that great podcasters all seem to have*.

* Although there are certainly some of the biggest names in podcasting who are brutal at this. We don’t speak of them in these parts though…

They are fantastic interviewers.

We might ascribe this to their having some sort of deep insight that allows them to latch on to the thinnest thread that their guest has presented. They are seemingly able to slowly tug on that thread and open their guest up with deep and meaningful questions, before ultimately weaving the interview together around a central theme.

We’re left moved and inspired by the interview. And we assume that this host just “has the gift”.

Well today we’re going to talk about how to develop your own interviewing skills that will make you a better podcast host, have more insightful conversations with your guests, bring more value to your listeners, and make your podcast stand out.*

* Oh, and your whole life is going to be a lot more fun and interesting!


The 4 Pillars Of A Standout Interviewer

In my experience, there are 4 elements that contribute to improving yourself as an interviewer. Keep in mind that none of these elements are inborn talents. All can be learned, and in fact, two of them leave you no option but to do the work to see the benefit. The pillars are as follows.

  • Research
  • Preparation
  • Listening
  • Adaptability

Sounds pretty simple right? Right now you’re probably thinking something along the lines of, “Really?? That’s what you’re giving us?? This article is a joke, I’m leaving! And I’m taking the Cheetos I brought with me…”

First of all, leave the Cheetos, I already ate half the bag, just let me keep the rest. Secondly, if these are so simple and intuitive, why aren’t more podcasters using them?

For one, because they actually take quite a bit of work, both to develop the skills initially, and then in preparation for each new episode.

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The Wrong Way To Interview

If you’ve listened to a fair number of podcasts you might recognize that there are a plethora of formulaic shows that go something like this.

  1. Intro
  2. Standard questions 1-10
  3. Couple of quirky questions unique to the guest
  4. Where can we find you
  5. Outro

If anyone’s still listening they’re bored to death by now…

Somehow, there are more than a few podcasts that have managed to build up followings with this type of show. But for the most part, I attribute that to those podcasters getting in on the trend early, and having really high-quality guests*.

* Who I would say they wasted with their bland questioning…

The strange thing to me is that few podcasters seem to pick up on the fact that truly massive and successful podcasts almost never follow this type of format, and in reality do something of the opposite.

Let’s look at the 3 pillars and you’ll begin to see what I mean.


Interview Pillar 1: Research

Ok, I’m not going to sugarcoat this for you, this one is just plain a lot of work.

The first step of any interview in which you hope to uncover some sort of insight, and cover new territory with your guest has to be research. You might not know your guest personally, but you should do everything you can to learn as much about them as possible. The reasoning behind this is threefold

  1. Get to know who your guest is, what they believe, where they’re coming from
  2. Find out what kind of insight they can bring to your audience
  3. Find out what they’re commonly asked in other interviews they do. What topics always seem to come up?

Researching your guest can take on many forms, and the depth into which you go is up to you.

A few methods of research I recommend are:

  • Read their book(s) if they have any
  • Read a number of their blog articles/listen to their podcast episodes
  • Listen to/watch/read past interviews they’ve done. Make note of the questions they’re asked
  • Talk to any mutual acquaintances about what you should ask them

As you’re doing your research make sure to note common themes and talking points, but also the things that really interest you about your guest, and that you think might interest your audience as well.


Interview Pillar 2: Preparation

Once you’ve finished your research it’s time to pull it all together into an interview plan. You can structure this however you want in a way that fits your podcast’s format, but what we want to make sure we focus on in this stage is some of the actual questions we’ll be asking our guests.

There are a few important categories of questions that I like to base my interview plans off of and that help me come up with better questions. Keep in mind that these categories can (and often will) overlap.

  • Contextual Questions
  • What Haven’t I Heard Before?
  • What Can They Offer My Audience?
  • Promotional Questions

If you’re interested in how I plan out my interviews, you can download the interactive PDF I use here.

Contextual Questions

These are questions that help establish your guest’s backstory, who they are and where they’re coming from. Usually, you would start off the interview with a few of these types of questions to help you both warm up to the conversation as well as help your listeners understand who the guest is.

These can also be a series of fun questions (think lightning round segment) either tailored specifically to the guest, or that you ask each of your guests. I’m a fan of both, and it can be fun to see how different guests answer the same questions.*

* Remember, we’re talking a couple of short questions here, not the whole interview…

If your podcast is on the shorter end, this would most likely be the first broad category of questions that I would recommend trimming down. These can also be some of the most entertaining bits of the interview, however, especially if you know how to ask the right questions and pull stories from your guests.


What Haven’t I Heard Before?

This is where you put all that hard work researching your guest to work. During and after your research you want to be thinking about what hasn’t been touched on in other interviews that you’re still curious about? If you’re curious, it’s a sure bet that you’re not the only one, and at least a portion of your audience is as well.

Too many guests make the rounds on various podcasts in their field of expertise, are asked the same questions, and give the same canned answers. If you want to stand out, you’re going to need to find a way to pull something new from them, and like so many of the best things in life, that starts with a little bit of curiosity.


What Insight Can They Offer My Audience?

This is a category strictly detailing the knowledge and insights that you know this guest can speak into for your audience. Again, you’ll have discovered many of these topics through researching your guest beforehand.

Note that many of these topics might have been covered extensively in other interviews. After all, your guest is likely an expert in one area with others also looking to gain a piece of that knowledge to share with their audiences.

That’s ok. There are some questions that just need to be asked regardless of how many times they’ve been covered before, and you shouldn’t shy away from them just because they aren’t “fresh”.


Promotional Questions

The last category is questions that help your guests promote anything that they might want to promote. It can be uncomfortable for some guests to really sell hard to an audience after an interview, even if their product might be super useful.

Try to craft questions that tease out what the product is and why it’s a good fit for your audience*. This will help your guest feel more comfortable with any promotion and helps your audience understand that you’re behind this product or service as well.

* But only if you actually believe it is!


To Be Continued

Ok, so we’re only halfway through, and this is turning into a mega post. So next week we’re going to cover the other 2 pillars of successful interviewers and podcast hosts, Listening, and Adaptability. 

Until then, feel free to grab the free interview planner below and start improving the quality of the interviews on your podcast, get better guests, and earn that reputation as a bad-ass, insightful, brimming-with-wisdom interviewer that we all aspire to!*

* Don’t tell me that’s just me…


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Jeremy Enns

Jeremy Enns

Storyteller In Chief at Ascetic Productions
Jeremy Enns is founder and Storyteller In Chief of Ascetic Productions, a podcast consultation, management, and production company that specializes in helping brands and entrepreneurs share their stories authentically. Besides strategizing with clients on how best to connect with their audiences, Jeremy loves ice cream, ultimate frisbee, and nerding out over Star Wars.
Jeremy Enns
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