Skye Pillsbury is a self-confessed podcast junkie and recovered publicist. She writes the daily Inside Podcasting newsletter and hosts a podcast of the same name where she interviews podcasters about their craft.

With her first season wrapped up, Skye is currently preparing to record another round of interviews for season two. Her meticulously crafted episodes take listeners on a journey inside the minds of some of the most successful hosts in podcasting.

In this interview, James Deeney speaks with Skye about what it was like to make her first podcast. They discuss Skye’s background in the tech industry, her personal obsession with podcasts, why she decided to get behind the mic, managing pre-interview anxiety, finding your own voice as an interviewer, approaching podcast editing like a puzzle, being purposeful about including diverse voices, and other topics.

We’ve extracted and summarised some of the highlights from the conversation below.

Follow Skye on Twitter @SkyePillsbury
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Podcast Theory to Podcast Practice

There’s no shortage of information out there for first time podcasters. And obviously, it’s a good idea to familiarise yourself with the fundamentals before you hit record.

Read up on the basics, then learn by doing

But it’s important to keep in mind that reading (or writing) about podcasting isn’t the same as actually doing it. As Skye outlines, there’s no substitute for first-hand experience.

“Most people assume there’d be a lot of carry over in going from writing the Inside Podcasting newsletter to hosting the podcast. But that wasn’t the case.

“There’s no doubt writing the newsletter helped me understand the theoretical side of putting together a podcast. But that wasn’t much help when it was time to actually make one myself. It was a big learning experience for me and continues to be.

“I’m really grateful I’ve gone through the process. In terms of carry over, it actually works much better in reverse. After producing my first season, now when I’m covering more technical issues for the newsletter, I have a much better understanding of what people are talking about.”

Learning to podcast is no different than learning any other skill. You need to actually do it to understand it on a deeper level. So if you really want to create your own show, don’t let information-gathering morph into a form of procrastination.

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Managing Pre-Interview Anxiety

In psychology, anticipatory anxiety is where a person experiences increased levels of anxiety by thinking about an event or situation in the future. And it’s something which plagues many new podcasters. Sitting down with an expert to have a recorded conversation can seem pretty intimidating.

 In the best case scenario, you’ll be able to transcend the anxiety with curiosity.
Pre-interview nerves are a part of the process

Every host wants their recordings to go well, but obsessing over upcoming interviews is usually counterproductive. For an interview to get into a natural state of flow, both guest and host need to feel at ease. To help alleviate some of the nerves, Skye emphasised the importance of choosing your guests wisely:

“I definitely wasn’t exempt from that kind of anxiety. So the first piece of advice I’d give is to follow your own curiosity. Only reach out to people you actually want to talk to. That way, your own personal interest can serve as your north star during the interviews. In the best case scenario, you’ll be able to transcend the anxiety with your curiosity.

“If you’re interviewing someone you don’t know much about, and it’s the first time you’re doing it, then your level of anxiety is naturally going to be higher. You can’t tap into what you love about what that person is doing. So if the conversation gets stuck, you’ve got nothing to fall back on.”

Skye went on to explain it's also important to leave enough time between interviews to prepare. Trying to record a handful of interviews in one week isn’t a great idea, especially if you’re just starting out.

“You want to avoid feeling frantic. Feeling like you’re short on time and still need to prep is a recipe for disaster. It can be a time consuming process, so leave yourself enough time to do it properly.

“Dive into your guest’s background. Listen to their podcast if they have one. If they’ve just published a book, try to read it. And if they’ve done other podcast interviews in the past, listen to them to get a sense of how they communicate and what they’re most passionate about.”

Prep is vital. But don’t go overboard. Afterall, there’s only so much ground you can cover in a single interview. Prioritise and focus on five to ten key questions, and keep any other talking points in your back pocket in case you do have time to use them.

How to Ask Better Questions

Ultimately, if a guest isn't giving you great material for your show, it’s not their fault. It’s yours. As the interviewer, it’s your responsibility to capture engaging material. 

If you ask the same questions everyone else does, you’re probably going to get a rehearsed answer.

Skye detailed a simple process she uses to craft questions that are more likely to get an interesting response.

“If you ask the same questions everyone else does, you’re probably going to get a rehearsed answer. Personally, I try to take the questions they’ve been asked before and take them one step further. For example, ‘I’ve heard you say X, but I didn’t really get a sense of Y. Could you talk a bit more about that?’

“Forming your questions in this way achieves two things. First, by conveying what they’ve already said elsewhere, you immediately move the conversation into more interesting territory. And second, you’re showing your guests that you actually pay attention to what they’re doing.”

Better prep means a better interview

Drawing up a list of great questions is important, but that alone doesn’t guarantee a great interview. It’s important to retain a degree of flexibility and openness during the conversation.

“In the best case scenario, you’re not just going to be reading off your list of questions. You’re going to start the conversation with questions and then your guest is going to take you on a journey. So you should follow their lead on that.

“It’s hard to get to a point where your feel confident not bringing written questions into the interview. Having them on hand feels like a security blanket. But trust me, if all you do is read off those questions the interview isn’t going to get to the place you want. Sticking to a rigid outline prevents you from getting into areas of real depth with your guests.”

Initial questions can help point your guest in a particular direction. But as an interviewer you need to rely on spur of the moment follow-ups to make sure you get the best possible final episode.

Being Purposeful About Boosting Diversity

In the past, podcasting definitely had a reputation for being the home of white men. Thankfully that’s beginning to change due to growing popularity. But it’s an ongoing process. In order for podcasting to be as successful as it can be, it still needs to draw in a more diverse range of listeners.

In podcasting, the path of least resistance is the path of no diversity.

Given this situation, many podcasters are seeking to create content that captures a diverse range of voices. Skye said the best way to achieve this as a host is to be open and vocal about the kinds of guests you are looking for.

“I recently read Kirsten Meinzer’s book, ‘So You Want To Start a Podcast’. It’s a great book. One of the chapters focuses on diverse voices in podcasting and I found it to be very direct and powerful. Kirsten doesn’t mince words, she’s very clear in her advice. If you want to include more diverse voices, you need to do the thing you’re afraid to do which is Google what you’re looking for.

If you are looking for Asian American voices, then use Google to find a relevant expert. Don’t be shy about taking that step. Put out a call that clearly states what you’re looking for. Because if you don’t make it explicit, it won’t happen. In podcasting, the path of least resistance is the path of no diversity.”

One of the great things about podcasting is that it enables everyone to have a voice. So podcasters who have a desire to increase diversity should take an active role in making the industry more representative. Things are clearly moving in the right direction, but there’s still work to be done.

To hear more from Skye, you can subscribe to the Inside Podcasting newsletter or podcast, or follow her on Twitter @SkyePillsbury

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Get the Podcast Crash Course video series for free. Learn how to create and share compelling audio that stands out among the noise.

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