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Issue #9 • September 2017

How to Become a World-Class Podcast Interviewer

Content Marketing Podcasting

Ira Glass, host and creator of This American Life, is one of the most powerful interviewers of his generation. But it was when he was in the interview hot seat that he delivered one of the most powerful quotes I’ve ever read or heard:

What nobody tells people who are beginners — and I really wish someone had told this to me– is that all of us who do creative work, we get into it because we have good taste. But there is this gap.

For the first couple years you make stuff, and it’s just not that good. It’s trying to be good, it has potential, but it’s not. But your taste, the thing that got you into the game, is still killer. And your taste is why your work disappoints you.

A lot of people never get past this phase. They quit. Most people I know who do interesting, creative work went through years of this. We know our work doesn’t have this special thing that we want it to have. We all go through this. And if you are just starting out or you are still in this phase, you gotta know it’s normal and the most important thing you can do is do a lot of work.

As a creator, if that doesn’t inspire you to do better work everyday, I don’t know what will. And without an interviewer to ask the right question, Ira Glass might never have said those words out loud to anyone.

That is the power of a great interview: it can change you as a person, it can change the interviewee, and it can change the audience who gets to listen in like a fly on the wall.

Whether you’re an experienced podcast host or you’re just getting started with your first show, this post is designed to help you level up your game and become the kind of interviewer capable of changing the lives of your listeners one special moment of audio, or “tape” as the pros call it, at a time.

The problem with most interview podcasts

Before we go any further, let’s cover the reality that exists and makes a post like this necessary. I see two truths about running an interview podcast:

  • Conducting a world-class interview is incredibly difficult
  • Most interview shows aren’t very good

The reason for this is simple: just about anyone can create an interview show. Grab the headphones that came with your phone, invite a friend to hop on Skype, hit record, and voilà, you’re a podcaster with an interview show.

This is how we got so many interview shows and so few interview shows worth a single listen.

What people want from podcast interviews

In the early days of podcasting, some shows with hosts just winging it worked incredibly well. There was a relatively small supply of podcasts to listen to, which meant it was easy to grow an audience. That’s where we got things like formulaic interview shows that ask the same exact questions of the past 1,000 guests while growing a massive audience; or the shows that barely get past surface level tactics and tricks with any given guest, leaving the humanity of the person for someone else to uncover.

Luckily, the Internet has a bit more of a quality filter these days, and that means there’s less room for new podcasters to jump in, wing it, and grow a huge audience. It also means there’s more room for very high-quality content meant to serve a specific group of people.

What people want from interview podcasts today is straightforward, but hard to deliver:

  • Great guests who can do some combination of inspire, teach, and entertain
  • An interesting host who prepares for every conversation, represents the interests of the audience in the interview, and sounds like this isn’t their first rodeo
  • Answers to questions they wish they could’ve come up with on their own, which reveal new information or present a different angle on what they already know to be true
  • A conversation that has a narrative arc but that isn’t scared to go off the beaten path

But more than anything, the people in your audience want to feel something as they listen to your show. That’s where you come in: to deliver the goods with an interesting, engaging, and inspiring interview show that changes your listeners in some small (or big) way every time they tune in.

Four principles for great interviews

So if we take what your audience wants and turn them into actionable principles for becoming a world-class interviewer as a podcast host, we end up with a list that looks something like this:

How to have a great podcast interview-CuriosityStep 1: Be endlessly curious

Any great podcast starts with the motivations of its creator. What are you in this for? That’s not an ephemeral question for later, I mean right now. What are you in this for? Why do you want to host a podcast?

Here’s what I’m scared of: you’ve heard podcasts are the next big thing. You saw Serial go from zero to darling of the world. You saw companies like Gimlet raise millions of dollars to create a podcast company. And you, well you just want a piece of the pie before it’s all gone. Let’s start a show and make some money!

Here’s what I hope is actually true: you have an insatiable curiosity about a topic or a group of people. You’re an anthropologist at heart or a storyteller who loves a good tear-jerking moment or a researcher who always thought academia was far too removed from everyday people to be useful. Honestly, you just can’t help yourself, a podcast just seems like the best way to find something inside of yourself that you simply have to express.

Podcasting is art. It’s beautiful. Audio is a powerful, emotional experience when it’s done well.

Jess Thorn, who’s been hosting a show called Bullseye his entire adult life, recently started another show. This one’s called The Turnaround and it gets its name from the fact that each episode is turning the mic around on a person who’s typically the interviewer. He digs in to find out how they became the interviewer they are today.

In a recent interview about what he learned from The Turnaround (so meta, I know), Jesse encapsulates the essence of what’s possible with an interview by saying,

I think one of the biggest things that I learned is that there is not a right way to do my job, and so I should stop worrying that I am doing it wrong. And instead, I should be thinking about a kind of broader philosophical question, which is: Am I open-hearted enough?

Are you open-hearted enough? Is that why you’re getting into this thing? The world has enough shitty podcasts. Don’t create another one. But a podcast from the heart – now that we have an infinite capacity for. Do that instead.

To be a world-class interviewer, you have to be endlessly curious.

How to have a great podcast interview- the right guestsStep 2: Invite the right guests

The whole deal with an interview show is that it’s a two-way street. You’re not the star of the show, you’re the shepherd of the conversation. Which makes your guest the star.

Here’s the thing you’re going to want to do: go find all of the most popular interview shows, look up all of their guests, find the overlap and invite those same people onto your show. That’s how those shows got big, right!?

It’s so tempting, so accessible, so… just don’t do it. It’ll be a cheap trick that gets you a few listens and then you’ll be another podcast in the pile of podcasts we know not to listen to if we want something unique and valuable.

If you’re starting or running a podcast, I assume you already know two things:

  • The topic of your show
  • The kinds of people who listen to your show

At a minimum you know your topic and you might know your audience. Typically knowing your topic means you can parlay that into an audience as well. For example, Romesh Ranganathan knew he wanted Hip Hop Saved My Life to be about… wait for it… hip hop. And the audience would be people who care about or are interested in… wait for it… hip hop. The topic begets the audience.

Now, this gets us to one simple question that can guide every invitation you’ll ever send to future podcast guests:

“Who knows something about this topic that is not famous, but should be?”

That’s all. That’s where all of the untold, interesting stories lie. The people who are not famous, but should be. Why? Because your taste tells you that this person has a story worth telling. That’s all that matters. If you want a slight modification, you can adjust to “Who knows something about this topic that isn’t as famous as I think they should be / isn’t famous to my audience yet?”

Side note: if you’re Barack Obama and you’re reading this, don’t take this advice. Just invite all of your famous friends to have coffee with you and record it. None of the rules apply.

But really, if you’re already relatively famous, or you have access to the famous people in your industry, none of this stuff about who to invite applies. Just do your thing with the most famous people you can find and you think are both interesting and related to your topic.

People will listen because of what made you famous or because of the famous people you know. This works especially well if you’re well-connected to people based on a topic that hasn’t been covered much in the podcasting world. Like hip hop or fashion or _________.

Oh, you’re not Barack Obama or Jessica Biel or Beyoncé? K, keep reading.

Now there’s pressure: you have to develop good taste and a good eye for stories when it comes to your topic. That sounds stressful, but it doesn’t have to be. You just have to use your curiosity about your topic as a tool.

Here are a few ways to uncover interesting people related to your topic:

Use Amazon as a tool to find the most interesting authors

Amazon is an incredible research tool if you use it correctly. Let’s say you wanted to start a podcast on practical ways your fellow humans can get educated about climate change and then work to reduce their environmental impact.

The most recent book you read on the topic was called Drawdown by Paul Hawken. Go to Amazon, type in the book and scroll down to the “Customers Who Also Bought” section. In it, you’d find a long list of books, some of which are also related to your topic, like:

  • A Global Warming Primer by Jeffrey Bennett
  • Big World, Small Planet by Johan Rockstrom
  • The Sixth Extinction by Elizabeth Kolbert
  • This Changes Everything by Naomi Klein
  • Tools for Grassroots Activists by Nora Gallagher

Five minutes of research and you’ll have a list of at least 10 potential guests. Do this with each book you’ve read or know about on the topic and you’ll have a laundry list of experts related to your topic.

Buy or download the last three issues of every obscure industry magazine related to your topic

Let’s say you’re starting a podcast on interior design. Search the web for “interior design magazines” and you’ll quickly get a great list without making another click:

  • Interior Design
  • Architectural Digest
  • Elle Decor
  • Dwell
  • Luxe
  • The Magnolia Journal
  • Veranda

And then there’s the academic journals, which often exist on almost any topic. Academic journals are where the real experts publish their research on the latest trends and findings related to the industry. It’s another angle you can take on your podcast or a good way to mix up the kinds of guests you invite. To avoid paying ridiculous fees for academic journals, join your local library and use their online database instead.

Once you find the relevant publications, write down the names of the people who wrote the articles, the people the articles were about, and the companies who advertise in the magazines. These will all be great leads for guests for your show.

Find the three to five niche conferences, festivals, or events in or related to your topic

Same drill, different resource. Let’s say you’re starting a podcast to help writers stay inspired, overcome their fears, and get connected to a community of fellow writers.

A quick Google search returns lists like this with any number of events for writers. It takes less than three minutes to find five events:

  1. The Bread Loaf Writers’ Conference
  2. Literary Writers Conference
  3. Community of Writers
  4. San Francisco Writers Conference
  5. The Muse and the Marketplace

Check out the site for each event, write down the names of every speaker and workshop leader, find out who hosts the conference, and maybe take a browse through the attendee list. That’s 100 potential guests within 30 minutes.

Find the people your past guests are connected to

This is old faithful. Every past guest on your podcast probably knows at least one other person who would make a good future guest on your podcast. If this were the only strategy you used, you would theoretically be able to keep your podcast going forever.

At the end of each recorded interview, you can ask your guest, “Hey, thanks for coming on the show. I know you’re well connected to [other writers, other environmentalists, other interior designers, etc]. Is there anyone you can think of in the industry that’s not famous, but should be?”

If all else fails, connect with each of your guests on LinkedIn and take a browse through their connections. I’d bet you’ll find a number of interesting potential guests there.

Ok, so if you follow these steps, you’ll have a list of a bunch of potential guests. You’re inviting them onto your show. Eventually you start getting “Yes, I’d love to” in return. What now?

How to have a great podcast interview- PrepareStep 3: Prepare like a professional

Some podcast hosts will just tell you to show up with an open mind and an open heart, no preparation required. If you can create a fascinating, high-quality show without any prep work, go for it! I say do both– show up open-hearted AND prepare.

Preparing like a professional means you’ll have enough context on your guest’s life and work to spark an interesting conversation. It also means you can be show up ready to truly engage rather than working from a script because you’ll have background information you can pull from at any moment.

There are three things you need to do in this phase of becoming a great interviewer: research, prepare an introduction, and make your guests’ pitch for them.

How to research

The goal of your research on your guest is to find out what is unique in this person’s story.

If you’ve invited guests that aren’t famous but should be, then your research might require an email exchange or a prep call ahead of time if there isn’t much to be found online. If your guest has a robust online profile, then you can research that way first and then fill in the gaps by talking directly to your guest.

There are four fundamental questions you want to answer in your research:

  • What about this person do you find so fascinating that you want other people to know about them? (In other words, why will your listeners care about this person after the interview?)
  • What have been the key turning points or crucibles in their journey to where they are today?
  • What fascinating habits, practices, or quirks does this person have that makes them interesting?
  • What makes them different from every other guest you’ve had on the show and how can you tell their story in a way that no one else has before?

To find answers to these questions, I like to do some combination of the following research:

  • If the person has done podcast interviews, I like to listen to three to five of them. This always gives me a sense of the basics of their story, as well as their canned pitches and anecdotes you like to use often, which helps me steer away from that version of the story in our conversation.
  • If they write online, I like to read articles they’ve written from different periods of their career. Three to five early articles, three to five from their middle years of work, and three to five recent articles. This gives me a good sense of how they’ve developed over time and how their views have shifted.
  • If they have written a book, produced artwork, designed websites, created music, or produced any other form of work, I like to find as much of it as I can and study it. I look for what’s interesting about it to me and take note of where the emotion is in the work. Finding the motivation that led to the work almost always leads to interesting conversation in an interview.
  • Study their LinkedIn page to understand their career path and what major career moves might have happened over their years to help them get to where they are. Imagine the people and situations that might have led to those moves.
  • If there’s nothing public, then start a conversation by email with your guest or ask to do a prep call to gather some of their story, motivation, and experiences ahead of time. It’ll help you skip the parts that won’t matter and drill down on the parts that do during the actual interview.

I use this research to fill in a prep document, or dossier, on the interviewee. You can download a template of that prep doc below.

Get our podcast interview template

Download template

I also use it to construct two narratives: an introduction and a pitch.

Provide a proper introduction (So your guest doesn’t have to)

There are two feelings that you don’t want your audience to have at the beginning of an interview: bored and awkward. Making your guest introduce themselves can lead to both.

You invited your guest onto your show for a reason. You’ve done research on them. You’re interested in their story. These add up to the perfect ingredients for a great introduction.

Here’s a great example of an introduction Jess Thorn gave of Susan Orlean on episode two of The Turnaround:

My guest this week is the writer, Susan Orlean. She’s been a journalist for over 30 years. She’s written for everything from Rolling Stone to Vogue and for the last 25 years or so she’s been a staff writer at the New Yorker. She’s also the author of several bestselling books. One of them, The Orchid Thief, you might’ve seen as the movie adaptation.

Here is Susan Orlean’s super power, and this is absolutely real. She can walk into any situation… she could walk into a town she’s never been to in Wyoming… she could walk into a party at [inaudible name]’s house… she could walk into the palace of a central European dictator… and she walks out with a story because she is the kind of person who is always ears open; who is always poking and prodding and pulling everyone around her until she sees that little glint of gold in her panning for gold pan. That little something magical and then she works it a little more and she works it a little more and all of a sudden she’s got a bestselling book.

Very few people are able and willing to give an honest assessment of their superpowers or what makes them amazing, especially in public. When you prepare an introduction like this for your guest, it honors all of their work and your reason for inviting them on the show without making your guest sell themselves at the outset of the conversation.

Perhaps even more magically, it means the interview can begin in the middle of the action, which is a powerful storytelling technique to grab your audience’s attention right from the beginning.

To take it one step further, you can also be the one to pitch your guest’s latest thing at the end of the interview.

You be the hype woman

Many people will agree to an interview with you because it’s mutually beneficial. You get a great story and they get exposure to your audience. For many guests, that means they’ll want to promote something at the end of the interview.

Most people aren’t very good at selling their own wares, and you know your audience better than they ever will. Use your pre-interview research to find out what the guest wants to promote and then write your own pitch for it to share at the end.

Something like:

I had a chance to read [guest’s] first two books and from the first page, they sucked me in. I couldn’t stop reading because of the power of the story and the depth of the research that was so clear throughout the book. [Guest’s] third book is now available and it’s called [book name]. If you listen to this show, trust me when I say that [guest’s] writing will surprise and delight you at every turn. Grab a copy of her book this week.

Now there’s no awkward exchange at the end of the interview, no questioning how long you should let the guest go on about their latest thing, and no hard feelings from your guest about why they didn’t get to share what they’re working on.

You’re done with your research. The interview is coming up and you want to make sure you get the most out of your time with your guest. Great questions are the key.

How to have a great podcast interview- ask the right questionsStep 4: Ask interesting questions

Turning all of that interest, prep, and research into a great live conversation is where all of the magic happens in a podcast interview– and it’s by far the hardest part.

Some people like to have a list of questions prepared based on their research. Others prefer to go into an interview without any planned questions, opting instead for a more intuitive approach. Regardless, you need to get comfortable with something that will feel terribly uncomfortable and unnatural at first: you can’t script another human’s responses.

The less you count on the conversation going exactly as you’ve planned, the better it will be. You can’t account for every possible outcome, so don’t try.

Instead, do three things that work in any situation:

  • Ask interesting questions
  • Listen
  • Trust yourself

When it comes to asking interesting questions, it all goes back to you being interested in your subject. Why did you invite them to have a conversation with you? Start there. Since you’ve already introduced your guest, you can jump right into the middle of the story– the action.

Your questions should probe for the emotion of their story. Ira Glass talks about the difference between ideas and stories. Your guest is most naturally going to share their ideas or their conclusions and learnings based on the story of their life. Ideas aren’t interesting in and of themselves; we don’t trust them when they stand alone.

But a story that leads to an idea, now that’s interesting. Laura Rosenfeld, writing for Tech Times, shares why stories shared on podcasts resonate so deeply with her:

laura-rosenfeld-quote

However, nothing stays with me more than a fantastic interview. I believe this is where the true power of podcasts lies because the ability to hear people tell their own stories in their own voices is an incredibly moving experience… There is something so deeply intimate about podcast interviews, revealing a tremendous amount of truth that makes me understand what a person went through possibly better than any other medium.

Your job as the interviewer is to ask the questions that get to that emotion, that story. Then you just have to pull on the string and listen to the story unravel for your audience.

Which brings us to that second skill you have to put to use in the interview: listening.

It’s so tempting to want to get ready for the next question. Your guest starts sharing a story, and you check out to look back at your list of questions to see what’s supposed to come next. In the process, you completely lose the opportunity to get to the heart of the current story. You miss the spontaneity of going down an exciting path your guest has never been down before in public.

You’ve probably heard one of those moments before. “And that’s when everything changed for us,” the guest says. “So, let’s change lanes here – what’s your favorite kind of candy bar?” the host says.

I’m exaggerating to make a point: if you listen, you can ask the follow up question every one of your listeners is going to be dying to ask in the middle of that amazing story your guest is sharing. You’ll also be able to hear it when your guest is using those same lines they’ve used in every other interview they’ve ever done and you can redirect back to something unique. And more importantly, you’ll hear a shift in nearly every interview that you’re doing your job right– it’s a shift from stranger to comfort. From your guest protecting herself from this strange person asking her questions to a more intimate experience that reveals the truth of the guest’s experience of life.

That’s when you’ve got the guest and the audience hooked. It’s when things open up. That’s the moment you’re waiting for in every interview. To get there, you have to trust yourself. You have to believe that in the moment when things start to open up, you have the skills and intuition and curiosity to take the interview in the right direction.

Sometimes you’ll miss the opportunity. You’ll listen back and realize you blew it. But as you gain experience, you’ll get more and more adept at asking the right questions to get things going, listening for the emotion, and trusting yourself to pull on the string at the right moment to unravel a fascinating story your guest has never shared in that way before.

Questions are at the heart of any great interview and they’re the tool of every world-class interviewer. All of the prep in the world won’t make you a great conversationalist. It won’t help you go from sounding scripted to natural overnight. But the better you become at asking great questions at just the right moment, the better your interviews will be and the more your listeners will clamor for that next conversation.

Now that you know the four things you should do to be a better interviewer, download our guidelines for the five things you should absolutely avoid.

5 Completely Avoidable Podcast Interviewing Mistakes

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The six best podcasts to listen to to learn how to be a better interviewer and host

One blog post will never be enough to help you become a world-class interviewer (spoiler alert), but I’ve done everything I can to give you a headstart. Becoming truly great at your craft as a podcast host will require you to continue to learn and grow over time.

I find that studying others who are already great at a skill I want to develop is a great way to continue to grow myself. Here are five podcasts I’d recommend if you want to study great interviewers in a variety of different fields:

  • The Turnaround with Jesse Thorn: As Jesse Thorn signed on with NPR for his first public radio gig, he realized he lacked the formal training so many of his new colleagues had benefitted from. So he decided to interview his favorite interviewers about the skill of interviewing. So meta, and so good. You’ll love hearing Jesse chat with guests like Ira Glass, Katie Couric, and Marc Maron on The Turnaround.
  • On Being with Krista Tippett: Krista Tippett might be the most empathetic and thoughtful interviewer in the world. She’s certainly a gift to the Internet, as every conversation she has on On Being is a delight and sure to make you think deeply about some aspect of your life or personality. Step into the booth with Krista if you want to feel more connected to your fellow humans.
  • The Ezra Klein Show with Ezra Klein: Ezra Klein is a founder of Vox.com and one of the most important voices in news media today. He has an outstanding intellect and ability to communicate complicated theories, complex political situations, and intricate histories in a way that helps you understand the significance of the topic at hand as it applies to your own life. On his show, Ezra invites people from many different backgrounds to nerd out about shared interests and fascinating topics ranging from collecting art to the dark net to fake news.
  • She Does with Elaine Sheldon and Sarah Ginsburg: Hosted by two documentarians, She Does is a generation-crossing, lady-centric podcast with everything made by women from cover art to soundtrack. These weekly episodes dig deep into intimate conversations with women in media, film, journalism, art, and tech to learn their background, philosophy and process- basically what brought their guests to where they are today.
  • Us & Them with Trey Kay: Too often we think about us vs them. We use our differences to create a feeling of belonging far too often and in the process we’re left with a divided, competitive environment to live in. But what if we made a true effort to understand people with opinions that vary drastically from our own? That’s the premise of Us & Them with Trey Kay and it’s the kind of show that will make you more empathetic and more understanding. We could use a bit more of both these days.
  • Hip Hop Saved My Life with Romesh Ranganathan: Because what could be better than a true hip hop fanatic interviewing people from across the industry to reveal what goes on behind the boards, where our favorite hits come from, and what it takes to make it in the music industry. Romesh loves hip hop and it shows in the way he hosts conversations with the people driving the industry.

To become a world class interviewer, host more interviews

With this article, you now have the tools to get started. If you read the rest of this issue of Tradecraft, you literally don’t need to read, watch, or listen to anything else to get started as a podcast interviewer.

The only thing that will truly lead you to become a world-class interviewer now is hosting more interviews with interesting guests. Every conversation you have for your podcast will help you practice what we’ve laid out in this article.

Regardless of how many interviews you do, remember two things. First, it’s someone’s first time every time– every episode you record, a new listener is discovering you. Second, stories change people. There’s never been a better time to be an independent creator (and in this case, podcaster). Changing people’s lives with story is a great opportunity and a great responsibility. Take it seriously, and make it great!

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Barrett Brooks

Barrett is the director of marketing at ConvertKit. He thinks of himself as a servant leader, entrepreneur, sustainability advocate, optimist, avid learner, writer and outdoor enthusiast. Based in Portland, OR, His work is driven by the belief that business is one of the most powerful forces for good in the world. You can find him hiking, skiing, reading, throwing a dinner party, or generally asking deep questions of the people he loves in his spare time.

Experience this issue your way

Download this issue of Tradecraft as a PDF to read and reference at your own pace.

  • I came here after seeing a post on a podcast-related Facebook group suggesting much of the advice in the September issue was bad advice.

    As a professional interviewer, I jumped to this article first and found it to be quite solid. Nice and thorough work here Barrett.

    I can’t speak for the rest, as I’ve yet to dive in, but I’m not sure I could have written a better article on interviewing myself, and I’ve been doing it for 30 years.

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