When you talk about what makes the best podcast interview questions, you have to talk about the mindset that goes into it. A curious mindset is always the best place to start. Being in that growth mindset helps set the tone for everything you do. You have to look at it from the perspective of learning something and connecting with people so you can put the same energy in it around the fact that people who are watching might learn something, too. Open-mindedness curiosity and networking that add to both your interview subject and your audience is going to make for a better interview no matter how you go from there and no matter what question you ask. Learn how to structure the best podcast interview questions as we delve into the seven types of questions you should ask.
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Structuring The Best Podcast Interview Questions
I’m going to talk about the best podcast interview questions. It’s a little more than the best questions, it’s the best technique for creating those questions. I want to put this in a little context because I’m an Inc. columnist as many of you know, and I’ve done about 180 articles and out of those articles, I would say 90 % of them are involved an interview of some kind. Tom and I have done hundreds upon hundreds. We’ve done over 530 episodes on one of our podcasts and about 100 on our other two. Almost a good third of them if not more, are interviews as well. This technique that I use for developing our questions is pretty time-tested and it becomes second nature after a while.
I don’t want you to get scared off that there is like, “I was trained at some journalism school and that’s what I’ve got here.” I do have some good journalistic practices that I researched, developed, and learned over the last few years, but for the most part, this is something that you can absolutely do yourselves. It’s a guideline for how you do this. Let’s talk about what makes good interview questions first and I want to talk about the mindset that goes into it. You’ve got to really be thinking about the fact that you have a job as a host or if you’re a journalist, you want to get a good interview out of it, you have to put in a tone to everything that you do.
That involves a little bit of mindset. A curious mindset I think is the best place to start. It’s always where I start. I want to learn something new, I want to grow my mind. Being in that growth mindset world really helps set the tone for everything you do. You’re not just there to do in and out, and this is just a marketing task that you have to get done and get over with. If you look at it from the perspective of, “I’m going to learn something here. I’m going to connect with people.” That’s the second part of the mindset that I want you to adopt. “I’m going to connect with someone. This is my networking opportunity.” You want to put the same energy in it, you do when you go to an event. Now is my event.
That’s how I look at that from everything that I do, those two things. I’m going to learn something and I’m going to connect with someone. Even if it’s only that someone, because it’s not recorded or it’s not live, when I do my Inc. interviews, I do record it for my notes, but I’m not going to air that. I still want to have that kind of energy and mindset around the fact that people might be watching this. They might learn something too. I’m always thinking about my external audience. I’m thinking about that as I’m asking questions. Even if I get it, I sometimes want to ask questions to delve a little deeper or define it a little more with the idea that maybe everybody listening or everybody who I’m going to write for, don’t know these things as well. Open-minded, curious, and networking, connective that to both your interview subject and your audience is going to make for a better interview no matter how you go from there. No matter what question you asked, but that is going to help tremendously.
The next thing I have are my seven types of questions that I asked and I like to use all seven types. Sometimes I don’t ask seven questions, sometimes they’re combined together or sometimes I reuse the same ones again. You’ll see as I go through them, why that is. Some of them have a sense to them and some of them are a specific type of question. The first thing that you want to do is, and this is probably the only one, there might be two of them that need to be in a specific order. This is the one that you want to start with first. You want to start with an easy question. I call it the at-ease question. You want to put your interview subject at ease, you want to make them feel comfortable. You want to toss him a softball, if you want to think of it like that. You don’t want to go in there and gang buster, attack them, and do any of that. It’s not going to serve you long-term even if you do want to challenge them later. I always like to challenge people, but you want to start at that. Put them at ease because there’s also sometimes, especially when you’re doing a live stream like this or a live interview, there can be nerves. We want to make sure that we’re covering that by putting them at ease.
The way that I do that is I go into something personal and passionate. You got to know a little bit about your subjects. Hopefully, you met them before, you’ve had a connection, and you can tell a little story about how you met. It reminds them that they get to say something and they say that was a great event. That way you can ease into your subject or into their bio and you don’t really just start with, like, “Who are you? You want to really give them something that is an easy question for them to answer, that hits them on the personal side. Either showing a personal connection between the two of you or shows that you have some knowledge of who they are, what they’re about, and maybe what they’re passionate at and ask them something about that.
It can be really simple like, “We just met at the Traffic & Conversion Show and I’ve been dying to get you on the show.” You could talk about the new things that are going on in SEO. That sounds like you’re going to dive into subjects, but you’ve made the connection about where you met. Just say, “I’d love to know what you thought of the Traffic & Conversion Show, What was the coolest thing you found there.” That way you’ve eased them into something they can talk, so there’s no issue there. You’re still keeping it really businesslike and not too personal. If that’s the way your show is or that’s the way your content is going to go. Instead of going, “How many kids do you have? How are you doing? What’d you do this past weekend?” If that’s your style, if that’s what your show’s about, then absolutely do it. You can ask them, “I know you’re big on meditating. What type of meditation do you practice?” You can get into something simple. Something that you know that they’re going to really talk about, easy questions. This is our top one, super simple.
Our second one is respectful questions and this goes to something that I’m going to say is the basis for everything that I do and how I develop my questions. Respectful questions are not my being really respectful of you, it’s part of that, but my showing respect for you as my interview subject is the fact that I researched you, that I know something about you before I came in to interview you. It’s disrespectful to know nothing about your subject and to sit there and wing it. They’re like, “Why the heck am I here? What happened?” This happens very often I find when I use certain interview placements. It’s usually the low-end interview placement companies. I’ve done it before where I’ve gone on the show, I’ve done all the research on them, they know nothing about me. It comes across really disrespectful and you spend most of the time as the interview subject going, is this going to be a waste of my time. We don’t want to do that.
Research is the foundation for everything and I do because I said, “I’m curious.” Setting that curious tone involves a bit of research. I don’t spend a huge amount of time on this, but if I’m going to ask someone to be on the show, someone suggests them to me and I don’t know them, the first thing that I’m going to do is Google them. It’s so simple. Google them, check them out on LinkedIn, check them out on Facebook, do something like that where you’ve at least gone in and figure it out who they are. The second thing I do is I go to their website and I check out their bio that they list there. On the bio they typically lists stuff like, I was in South by Southwest this March. I was featured there as a live podcaster from the stage. There’s a video there somewhere of me doing that. You should click that and check it out. If someone says they were at a TEDx Talk, I’m absolutely going to watch that. It doesn’t take a ton of time and you’re watching content that they’re proud of and they’re posting. Don’t just take it and say, “I’m a TEDx speaker.”
What if they’re TEDx Talk was not at all in the subject matter that you want and because it’s at the top of their bio that they’re really proud of this. They’re probably going to talk about it and it has nothing to do with your audience. You would have made a mistake by choosing that, by not just doing a little bit of homework. The other thing that I check as an Inc. columnist, this is something we’re trained to do, pretty much required to do because we’re required to put good, valuable sources in front of you as my readers. When I Google you and I check your website, I make sure this is a good website. I make sure it’s not from 1998. I make sure that you’re keeping it up-to-date, you’re with it. Maybe you’ve got some new YouTube videos, you’re adding content to it. I’m checking that out because if you’re not doing those things then you’re not going to do a good job of sharing my content. As a podcaster and as an Inc. Columnist, that’s what I want. That’s a little bit of my research too.
Once I do that research, maybe there’s a couple of things that I want to read a little further. I want to know a little bit about more about. I saved a few blog posts, other things, or videos that I want to watch later. A day before my interview I go and I refresh my mind. If it’s last minute, I’ll do it an hour before my interview, but that’s rare. I usually like to do it the day before so I can mull my questions over, so I don’t have to really sit down and draft anything out. Think about it, if I’ve been contemplating it for 24 hours, I know I’m just going to be able to rattle off my questions and not look at my list. You can see me looking at my list here. I’m going to share this with you. It’s just an overview of what I want to talk to you about. There’s no questions there, there’s no script, none of those things. Just a little thing so I stay on course and I do that. I do that same thing with my questions. I don’t write out the full questions. Like, “How did you prepare for your TEDx Talk?”
I would put a little note TEDx Talk and it’ll key in my mind the questions that I want to ask in the way that I want to ask them. This is the part of being respectful of it is that if you’re mulling it over, you’re thinking more, you’re thinking more about how you’re going to be able to be respectful of your audience too, and what they care most about. If you’ve had some time to reflect on that, then that’s coming across as well. So easy questions, first, second question are respectful questions that show a sign that you’ve investigated them a little bit, that you’ve explored this topic, that you’ve explored this guest, and you how to make it relevant for your audience. That’s really what it is.
You’re going to ask them a more in-depth question, something that’s just not as obvious about is like I just said, “How did you prepare? I saw your TEDx Talk, but how did you prepare? My audience would be curious about that. Some of them are aspiring TEDx Talkers. These are the things that you want to reflect in that second set of questions that you go through. The next type of questions that I do are what I call defining questions and these can happen at any time in the conversation. I have my podcast Product Launch Hazzards and it is for product launchers. People entering products into the consumer market, retail, mass market, retail, and eCommerce. When we do it, there’s a lot of acronyms thrown around. There’s like SKUs which my blog posts team went crazy over because they thought it was skew instead of SKU, stock keeping units.
As a host, even if I know what it is, if I’m doing a live podcast, it’s not something that I’m doing for my Inc. column because I know that term already. I will define it in my article. I want to define it for my audience, I want to explain what it is, and I want to make and I don’t want to just do it myself. I usually say, this is how we define this, do you define it the same way or is it something different? Or I ask them, would you please define that for my audience because I think we might have a lot of newbies out there and they could benefit from your explanation of what this is. Go ahead and use those defining questions to really help bring it out. Remember you have people of all level listening to your show and you really want to make sure that they’ve got a broad understanding of what it is. You want to be respectful of their audiences and at their learning level as well.
For some people, it might be old school, but they might be really interested in hearing how your guests define it because maybe they’ll use a slightly different definition. I find for a lot of things unless you’re really just asking them to tell you what the acronym stands for it and usually if it’s just that simple, I just spout it off myself and say, for our audiences, stock keeping units, that’s what a SKU is because it’s not worth going deep into defining. If it’s defining something more in-depth like content strategy or content to commerce, I’d be like, I never heard you say that before, can you explain that to me. That’s really something that you all want to do it with those third types of questions.
The fourth type of questions is the most important questions to creating bingeable content. To being a show that I want to come back to and listen again and again. It’s not about the entertainment value here. That’s important too. You need to be engaged, passionate and entertaining. In everything you do, don’t ask dry questions. Framing questions, and when I talk about framing, I’m framing it for my audience. I’m framing up what’s the value in it for them. I’m always thinking about how I can make whatever is being talked about, relevant. I mentioned before someone might come on my show and talk about SEO, search engine optimization. That sounds like a really boring subject, but it’s really critically important to understand the power of your blog posts as podcasters. How can I get more Google power and how can I do it? I might have to put that in context so to say, “We’re not going technical here and we’re not talking keywords.”
I really want to get this through to you about what it does for so many other sites that you don’t know about. Can you tell me about some of your big brand, websites that you’re working on doing this search engine optimization? What are my small independence competing against? I framed that up for him and when I do that, it helps my guest be more focused on our audience and understand them better. They may not from the get-go. They may not be an avid listener of my podcast. I need to make sure that I framed up what I want them to talk about, the angle that I want to take on it because it’s going to be most valuable and most useful for my audience. It really helps them look fantastic. It helps them pull ideas and case studies and examples out of their head that might be more relevant than the one they might just choose to talk about if I didn’t give them a framing question.
It means you might ask a little bit longer question, which isn’t always the best way. People want to hear your guests talk, but when you’re asking a relevant question, this is time where you could go a little bit longer because you want to give your guests enough information so they understand that framework that you want them to answer within. These are the questions that should be a little longer. The other ones can be shorter and should be shorter, they’re here to listen to your guests talk. You can talk in the pre and the post. That’s your opportunity.
The fifth type of questions I do go about are challenging questions. By challenging, remember I said I like to create a respectful tone in how I do it. I don’t think we have any podcasters. There are ones that are very challenging subjects and are discussing hard subjects, but I don’t think they do it in a mean and provocative way. That they’re just trying to be the devil’s advocate and they’re really just going to nitpick and push you. It’s not nice and respectful. I don’t think there’s anyone out there that we’re coaching or that we have in our network that are like that. I think probably because we’re on a network that does business podcasting. We’re in the business of making money off your podcast, not just doing high entertainment value with tons of advertisers who are going to take more money for the crazy show that you’re putting on. That’s just not what we’re about here. We just don’t tend to attract that. That doesn’t mean that you don’t want to challenge, dive deeper, and ask stuff in context.
I’ve had an opportunity to interview a lot of really great experts with decades of experience. I find sometimes that you have to challenge them and say I know that you’ve got this model, but how does this work in a digital market, how does it work with declining trust among brands, how does it work with this in mind. You’re challenging the sound bites, and the things that they’ve been doing again and again and talking about everywhere. You’re challenging them by saying, does this really work, and I want to hear the examples of that. Push them harder. Especially, when they’re spouting off stuff that sounds rehearsed, you want to push them into a place at which they’re uncomfortable and ask them something that really puts them on edge.
I’ve told this story not very often before, but early on in my Inc. column, I had an opportunity to interview Joe Gebbia of Airbnb. He’s one of the founders of Airbnb. The reason why I had an opportunity to interview him is because I’m a Rhode Island School of Design Grad and so was he, although much later than me. He thought it was interesting to get an online journalist who was asking, who was a RISD grad. It never happened before and he thought it would be cool. He gets on our interview, he starts talking with me, we’re going through it. I’m getting a little frustrated because everything that he’s answering sounds just like the TEDx Talk I watched. Just like the article, the interview he gave to Forbes. It sounds too much like everything that I researched about him. It sounds exactly like he got prepped and rehearsed by a PR agency.
I was getting very frustrated because I felt like I couldn’t write this story. It’s just going to be the same old stuff and that wasn’t what I felt my column was about. This was early in the early days. I pushed him a little bit at the end and I said I see these things going on in the news where you’re being challenged by illegal challenges by cities across the country and all of these things. You say you’ve got all this handled, Joe, but what’s really the big challenge for you in growing your business when you overcome all of that, what’s next for you? He just got silent. He didn’t say anything. He got weirded out by it because it meant that he had to go off book. He finally said, “I’m going to have to get back to you on that. I don’t know if I can talk about it yet.”
I said, “Get back to me on that.” I waited a week and nothing happened. I called my editor and I said to my editor, there’s no story here. I know you wanted me to write this, but there’s nothing new here. He told me the same thing. I asked them this question and this is what he said to me. I’ve pinged them and they aren’t getting back to me. She said, “Then don’t write it because it’s not worth reading.” I say the same thing as if they won’t answer those kinds of challenging questions where you push them to ask about stuff. It’s a fair thing for them to say, “We’re working on something that’s so secret. I can’t talk about it, but here’s what I can talk about.” Then find some other way to give you some answer to it. It may not be worth airing. That’s always an option for you is if you feel at the end of the day that they’re not giving you something that’s relevant in this world, those challenges are important for you to assess that. This is where I think the most important questions can come from.
My number six is my other most important questions that I ask which is follow up. Follow-up questions are the best questions you will ever ask. They are certainly not the ones you would ever script if you script your questions, if you wrote them down ahead of time because you can’t write because they say something and you got to follow up with it. It’s a follow-on question that you hadn’t thought of before. Here’s where I feel that inexperienced podcasters leave off. They leave off the best podcast question they could ask. That is the one where the audience is sitting in their car going, “Why didn’t you ask them that? I would have asked them that.” That diving deeper and getting to that more the heart of that question, the heart of what they’re saying. Making them clarify, and expand these follow-up questions are probably the most valuable questions you will ask. This isn’t something you can plan, you have to just be always looking for that opportunity.
The way to be looking for that opportunity is to be in the moment, do not be distracted. That’s why I like to do my interviews with a live person at the other end. I don’t want to have my camera off. I want to have my camera on when I asked the question. I conduct my interviews via Zoom or Skype. Even for my Inc. articles, which there’s no reason to have a video for it. I’m never going to air it. I’m going to have a written document. I’m going to have a written article at the end of the day. Doing it makes them believe and understand because they can see me of my engagement with them. In that engagement, it forces you to be in the moment, it forces you to listen, it forces you not be distracted by all the messages that start popping up on your screen because you’ve turned all of that off to record properly. Being in that moment allows you to access those wonderful follow-up questions, which I guarantee you it will be the most valuable thing that will make you bingeable.
That will make people want to come back because they’re like, she doesn’t miss those questions. She always asked them, I’m going to always get my full value out of everyone that she talks to. That I think is really important. My last set of questions is personal questions. This happens to me or whole lot. I got a lot of data. I got a lot of information. I’ve interviewed a lot of people. I can pull out a lot of stories. I can talk about lots of things and lots of other people. I’m very knowledgeable, but somehow in that sometimes it doesn’t get human enough. I go on a show and they’ll pick my brain about the topic and the subject. Especially for your podcast, there are really niche markets and areas, and you’re not doing a show that’s more of this personally based show or somebody’s personal journey.
You don’t get often to get it deep dive into who they are as a person. At the end of your show, if that didn’t happen, if it didn’t come across and it didn’t personalize this person, you want to also really make sure you’re taking them up off that pedestal and making your readers believe they’re human and accessible. It’s your job as the host to help them do that because they are in their expert mode. They sometimes forget to be real, be the human that they are. This is a time for you to ask a personal question and you can ask them and say, “You’ve got this all together, you’re always on stage. You’re always doing all of these things, but do you ever have doubts? Do you ever second guess yourself?” Now, you’ve allowed me to come down, be real, and be the person who I am. Be in the moment to share my real personality, my person. That is going to help your audience connect to you and to your guests in a greater way.
It’s also going to build a great rapport with them because now they feel that you got personal with them. You’ve got to know them. Maybe you ask them about their family because you’re like, “We didn’t talk about this at all, but you’re all over Pinterest and Instagram with wonderful, beautiful pictures of your kids and your product photos.” I have a client who has pictures of his kids, tell me about why you chose to do that? I guarantee you they will go and they will chat about it. It’s going to be really warm, it’s going to be a great story, and it’s going to really help end the tone. If you feel that that’s not the best way to enter show you want to end with some more hard-hitting things, you can go back to this just saying, “I love that story.” Now, “If you were advising your kids how to make it past this horrible hard startup stage, what would your advice be?” Then you get them back to the list of tips that you might want to end on. The recap of where you want to end on.
You can always pull it back if you’ve done that. You can do it at the beginning, you can do it at the end. I think at the beginning, it sets them a little off the expertise mode. You want to do it so that they are a person. You’ve gotten personal, thank them, then connected with them. At the end, it’s a nice way to close and make them human. Anyway, those are my seven. We’ll review them real quick. Easy questions, respectful questions, definition questions, you’re always looking for those. Framing questions, you always want to frame something up for your audience. Challenging questions to push them and make sure that their information is still relevant to your audience and it’s going to work.
Six is follow-up questions, you always want to look for the good follow-up and seven is personal questions. There’s a little bonus eighth that some people recommend and do. I want to just mention it, it’s not something that I’m a big fan, but for some blogs and some sites, this really works for them and it has. It’s something that they want to do. They go for the rapid five questions that I’m going to ask you, “What book are you reading? Why are you reading it? What are you eating today? Are you hacking your body?” whatever the rapid five questions are.
One of my favorite people, Abby Levine, she likes to ask weird questions. I was on her show and she asked me, “If you had a magic wand, what would your skill be? If you were in Harry Potter and you had a magic wand, what would your skill be?” I was like, “That’s a totally fun question. I love it and it’s really cool.” If you’re going to do either of these rapid-fire questions or something off the beaten track, please send them to your guests ahead of time. These are not ones that you want them to be that scripted on, but you also don’t want them to be a deer caught in headlights. “I don’t know what you’re doing. This is weird. I thought I was on a professional show. What’s this all about?” If I didn’t know Abby and she’s amazing and she’s fun and this is who she is. She’s got that child-like fun to her. She’s forcing fun into her show and I can appreciate that, but if she didn’t warn me ahead of time so I could get a fun thought in my head, it might make me look stupid.
As the guest, that’s not a good place for you to put them in. Ask these questions. If you’re going to give them just say, “Put them in your prep interview tips.” We send that out as an email. When someone books with us about a week ahead and 24 hours ahead, they get a set of interview tips. We tell them how to have your microphone, how to have your headphones, like all the things you want to do to your environment to make it good. If you were going to have those kind of questions, that’s the place to put them in. Say, “If you haven’t watched our show or listen to our show, these are the rapid-fire questions we’re going to ask you at the end, so be prepared. That’s a fantastic way to do that.
Now, here’s what I don’t like about those rapid fire questions. When you ask him like, “What’s your favorite book? What products have you bought lately?” These are pandering to the affiliate links k thing. I think that’s an okay thing to do if you do it deeper. In other words, if I’m going to tell you what my favorite book is, you’re going to then ask me why do you like that book so much and you’re going to let me give a testimonial against that book. Then you’re going to use that a little bit deeper. You can post it on Amazon as a review quoted but on your show like you can go a little bit deeper to it. You are more likely to get that affiliate link to be clicked if you do that. Make sure that if you’re going to do those things, do it better than the gurus out there who just say, “Do this. You’ll get a residual few percent of income.”
It’s really such a waste of time and it devalues your show because it looks just, it looks like you followed some cookie cutter advice. If you’re going to do it and you want to have that, it’s a part of your strategy. You make money on your site from that, make sure that you dive a deeper, give it a little more depth and a little more background. I think that’s the best way to go about doing that. I am so glad you guys joined me for the Best Podcast Interview Questions and I hope this was really valuable to you. You can find us on the web at FeedYourBrand.co. You can find me sometimes here on Facebook @FeedYouBrand live, but you can always ping me in the Facebook page at any time.
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