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    Dynamic Interview Questions for Creative Podcasters

    Every podcast guest has their own story to tell, but not just one. They’re full of potential stories that you, the interviewer, have to bring to life with the right questions. However, some guests are more comfortable than others when it comes to sharing their thoughts and insights.

    Does that mean you should cross your fingers and hope for the best? Sure, if you want to run the risk of having an awkward conversation that your audience probably won’t enjoy. Rather than wing it, borrow from this list of questions. 

    Guests are full of potential stories that you, the interviewer, have to bring to life with the right questions.

    Put your own spin on them and listen — you’re likely to get answers that are entertaining, informative, and really allow your guest to open up. (However, keep in mind that a conversation needs pauses that give your guest time to think. At the end we’ll go into the power of silence, Simon & Garfunkel style.) 

    Let’s get started.

    What quarantine hobby did you attempt to start but have already given up on?

    Remember when social distancing first began and everyone you knew tried making their own bread? Perhaps your hobby was something different, like learning guitar or starting a garden.

    This is a great question to ask early on in the conversation because it shows empathy with your guest and makes them relatable to your listeners. We all had high hopes we’d finally paint that guest room or learn how to woodwork, but quarantine life is exhausting. Hearing your guest admit sometimes they just want to relax and not work on a new project is impactful and sets the stage for a wonderful conversation.

    What’s the worst _____ you’ve ever had?

    You can tailor this question to your guest’s specific industry. For example, if they’re a musician, ask them about the worst gig they’ve ever had. Have an entrepreneur tell you about their worst pitch meeting. For a comedian, you’ll want to hear about their most cringeworthy show.

    Much like the quarantine hobby question, the goal here is to have your guest acknowledge a failure. While these moments were terrible as they happened, they make for delightful disaster stories after the fact.

    What do you remember about the first time you _____?

    Again, adjust this one to best fit your guest’s expertise. For example, ask a musician about the first time they felt connected to their instrument, let an entrepreneur describe the first time they landed an investment, or have a comedian recall the first time they saw their hero perform a set.

    By phrasing the question like this, asking what they remember, you’re encouraging your guest to dive back into a fond memory. You’ll often hear a smile in their voice as they reflect on the entry point to their career journey, whatever it may be.

    What’s something that’s surprised you about your industry?

    A twist on the traditional “What’s something you’d tell your 18-year-old self?” question, this is one surprise most guests won’t mind.

    Whenever you can take the opportunity to educate your listeners, you pounce on it.

    Chances are your listeners are in similar fields to your guests, which is why they’re interested in your show in the first place. They may not be as far along as your expert, so getting a heads up on something they’ll encounter later on down the road is incredibly helpful.

    Even if your audience works in an entirely different industry, you’re still enlightening them — and they may be able to apply your guest’s answer to their career anyway. Whenever you can take the opportunity to educate your listeners, you pounce on it.

    What’s a common myth or misconception about your job you’d like to call out?

    You almost certainly have a friend or relative that spreads misinformation. They’ll post articles with misleading headlines to social media, claim they heard a fact from a random third-party source, or even merely make up something to further their own agenda or support their position in an argument.

    Guess what? Your guest has heard plenty of misinformation about their job, too. Giving them a chance to set the record straight will not only provide a sense of satisfaction on their end, but it will also educate your audience. You’ll almost see the “the more you know” star shooting across your computer screen.

    What are you curious about that has nothing to do with your job?

    All work and no play makes Jack a dull boy, and it also makes your podcast much less fun. Your guest may be fully entrenched in their career, yet even the busiest of professions still offer downtime for other curiosities.

    If you phrase your question by asking what someone is curious about, it gives them a lot of different options to answer. It might be something from a field they’ve always wanted to explore, or it could be something totally outside the box, like presidential fun facts.

    Your guest is diving into an area where they’re not expected to be an expert, which actually opens up the door to chat more freely.

    People get excited talking about their passions. Your guest is diving into an area where they’re not expected to be an expert, which actually opens up the door to chat more freely. 

    By the way, here’s a presidential fun fact for free: James Madison was our shortest ever Commander in Chief, standing at 5 feet, 4 inches.

    What is your favorite curse word?

    I was asked about my favorite curse word during a job interview one time, and it made me stop and scratch my head. That’s part of the brilliance of this question — it gets people to pause and really think about their answer.

    You’ll get a sense of how their mind works, too. No one will merely say, “My favorite is bollocks,” and that’s the end of it. Instead, they’ll give a reason or two as to why it’s their favorite. Even in asking this question to friends, I’ve learned several new insults, inside jokes, and exciting looks into people’s psyches. It’s a &$%^#* fantastic time.

    Embrace the sound of silence

    “The Sound of Silence” may have become a meme in recent years — appearing in everything from “Arrested Development” to Ben Affleck interviews — but Simon & Garfunkel were onto something with their hit 1965 song. The sound of silence can be a beautiful thing, especially during a podcast.

    The next time you think your guest might be holding back a bit, try staying quiet for a few seconds after their answer.

    Here’s why: Silence makes most people uncomfortable. And instead of embracing that feeling, they’ll try to fill it. That’s good news for you as a podcast host, as they’ll usually say something else that will be useful for your audience. In fact, their “second” answer will often be even more valuable than their original statement.

    The next time you think your guest might be holding back a bit, try staying quiet for a few seconds after their answer. They just may add an invaluable nugget.

    Whether you’re a seasoned podcaster or just getting started, these questions can help kick off a conversation or get one back on track. Give them a spin on your next episode and feel free to reach out if you’ve got a favorite question to ask, too!

    Joey Held
    Joey Heldhttps://joeyheld.com/
    Joey Held is a writer, marketer, and podcaster from Texas. He hosts the Parks n Wrecked and Good People, Cool Things podcasts and loves helping people tell their stories and hone their message to best serve their audiences. When he’s not podcasting, Joey can be found shooting hoops, cuddling with his pups, or rocking out with his band, Burning Years.
    Podcast Movement 2021

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