No. 058 How to Plan Engaging Podcast Interviews

This is the second lesson in our three-part mini course about how to book, plan, and execute engaging podcast interviews.

In this lesson, Jonny leads a deep dive into the fundamentals of planning a great podcast interview. Not simply a ‘do this next’ discussion, but a look into key mistakes Jonny made in planning his first 200 interviews — and more importantly, how you can avoid these mistakes yourself.

Making it easy for our guests to book an interview with us is key. Luckily, there are a lot of tools available to us as Showrunners to make this as easy as possible. We go over a couple options to get you rolling.

We all want our interviews to be deep, authentic conversations with our guests. Often times the easiest way to accomplish this is with planning, but it can also be as simple as staying focused on setting up your guest to be awesome.

Along with all of this talk about interviews, Jonny and Jerod provide two more podcast recommendations for your listening enjoyment:

Listen, learn, enjoy …

The Show Notes

No. 058 How to Plan Engaging Podcast Interviews

Jerod Morris: This is Rainmaker.FM, the digital marketing podcast network. It’s built on the Rainmaker Platform, which empowers you to build your own digital marketing and sales platform. Start your free 14-day trial at

Welcome to The Showrunner, where we have one goal: teach you how to develop, launch, and run a remarkable show. Ready?

Hey there, and welcome to another episode of The Showrunner. This is episode No. 58 of The Showrunner. I am your host, Jerod Morris, VP of marketing for Rainmaker Digital. I am joined, as always, by my co-host Jonny Nastor, defender of humanity, connoisseur of coffee, and erstwhile auditor of energy, I believe was what you were in the last newsletter.

Jonny Nastor: That was a last-minute change, but that is definitely what I was last week.

Jerod Morris: Right, because originally you were runner of shows, which was just a little bit too obvious.

Jonny Nastor: I tried to slide that one through, but apparently my co-host would disallow it as a cop out.

Jerod Morris: Hey, that guy has high standards.

Jonny Nastor: He does. It’s good. That’s actually a real good benefit of having a partner in these kinds of things. When you can just get lazy and be like, “Oh, I’ll just do it and just do it,” the other person is going to step in and be like, “Come on, man. What are you doing?”

Jerod Morris: That’s right.

Jonny Nastor: So it makes the whole performance better.

Jerod Morris: Exactly. So what is an erstwhile auditor of energy?

Jonny Nastor: Five years ago I think, I did three years of … in Canada, the Government of Canada plus the province of Ontario that I live in, did government grants to make your home more energy efficient. Before that would happen, I was an energy auditor, it was called.

I would go in and take pictures of your house, measure it all, see what kind of windows, insulations, all that stuff. Then we’d do this software thing for it and see how much energy it used. Then they would do a whole bunch of renovations. I would go back and verify all those things and then get them a bunch of grant money.

Jerod Morris: Wow. It’s funny how you can read something and be so totally off. I was totally not reading that literally at all. I was thinking it was some reference to Scientology or some motivational thing that you looked at.

Jonny Nastor: I really let you down, wow. No, I literally was.

Jerod Morris: You’re a literal auditor of energy.

Jonny Nastor: I was a literal auditor of energy.

Jerod Morris: Okay. All right, very nice. If someone were to audit my energy right now, they would find that I’m very excited because we are continuing on with our series on mini courses. Of course, our series on mini courses is very meta because we are recording the content for our mini courses right here on these episodes of The Showrunner.

Jonny, on the last two episodes you did the first lesson in your mini course, How to Book, Plan, and Execute Engaging Podcast Interviews. I did the first lesson in my mini course on creating your unique snowflake in a blizzard of podcasts. Now, we’re alternating back. It’s your turn, and then next week it will be my turn again. I am excited to hear what you have prepared for us here regarding how to plan engaging podcast interviews. Are you ready?

Jonny Nastor: Born ready.

Jerod Morris: Born ready. Let’s do it.

Lesson 2 of How to Book Plan, and Execute Engaging Podcast Interviews: Preparing Yourself to Give the Best Performance Possible

Jonny Nastor: All right. This is the second part of the how to book, plan and execute engaging podcast interviews mini course. In the first section, we went over how to book. At this point, now, in the stage, we have the guest scheduled and ready to come onto our show. Now it’s our job to plan and ready ourselves and prepare ourselves to give the best performance for our listener and the best performance for our guest.

We’re going to break this into three sections again. We’re going to go over doing the research beforehand, then setting up your guest to be awesome, and then we’re going to work backwards.

Jerod Morris: Beautiful.

Jonny Nastor: Let’s do it.

Why Showrunning Is About Giving a ‘Performance’

Jerod Morris: Can I ask you one quick question before we start? It’s interesting that you mentioned the word ‘performance’ when you were just talking. We typically think, when we’re doing an interview, that the other person, your guest, but you also really need to be mindful of yourself and putting your best foot forward as the interviewer.

Part of the way that you do that, obviously, is setting up your guest to be awesome, but that’s also, in part, as you’re going to talk about here with doing the research and doing everything, is preparing yourself to give the best performance possible–even if that’s just asking questions and engaging and asking good follow-up questions.

That’s an interesting little mindset tweak that maybe people don’t really think about when it comes to doing interviews.

Jonny Nastor: Yeah. I like that. You’re right. It’s wrong to not think of any of this showrunning experience as a performance because it is. It’s entertainment. Even though we can be educating or inspiring, we should be also entertaining to some degree. Otherwise, people won’t want to listen to us.

Step 1 of Giving the Best Performance Possible: Do Your Research

Jonny Nastor: All right. Let’s do this. Do your research. I have three steps for doing this, and this can be almost as thorough or as basic as you want it to be. Depending on what you’re trying to accomplish, which we’ll get to, you do need to have these things covered. I find this mostly because you don’t want to just be asking questions that are just too obvious.

Not just for the fact that they might be too obvious and that your listener might know about it already, so it’s not as entertaining. But also because it loses engagement with your guest, I find. If it’s just the same thing over and over again, it’s like, “Wow, you didn’t look into me at all.” All of the sudden you’ve lost.

We’re doing this over voice only usually, so it’s really key that we know certain aspects so that it shows that we’ve put some time in and that we’ve put our effort into making it a good performance for the listener. Then I find that the guest enjoys also stepping up.

Learn About Your Guest from Social Media

Jonny Nastor: What I used to do was, I had an assistant that would do all my research for me, and then I found this beautiful free app called Charlie App. Charlie App can either connect to your Chrome or connect right to your Gmail, I believe. I’ll link to it. It’s, and it’s a completely free app that connects to your Google Calendar, your Apple Calendar, whatever you use.

Any appointments, any scheduled interviews that you have, it pulls data from that person just based on their email address, their Twitter, their LinkedIn, and it just aggregates all that and sends you one email an hour before. You can set to even be a day before if you wish. Then it compiles that information for you so that, basically, I can just go through it. I can click. I can look at their Twitter. I can look at their LinkedIn.

Social media, to me, is a really good place. It seems a bit lurky. But I find it interesting, and my guests always seem to respond well if I go, and during our interview, I’ll mention something they Tweeted or Retweeted in the last week or something. It shows that you’ve done your work, and it’s completely open. Most people’s Facebook is closed somewhat, but Twitter is completely public. You can see who they follow. You can see what they’re into. It really gives you a good insight I find.

Then the other social media that I get from Charlie App is LinkedIn. As much as I dread going on LinkedIn, I do go onto it for every single guest that I do. It gives me a great background of their work history, which can really tell you a lot about the person in general, where they’ve come from. You can hopefully weave that into the conversation so that it’s not just, “Well, I looked into the last three months or something of your life.” You have this overview. The information is there.

That’s why people post that stuff to LinkedIn, so the people doing research on them or wanting to know more about them can get that information. Take the time, go get that information, and then bring it back and use it to prepare yourself for this interview.

Know How to Properly Pronoun Guests’ Names

Jonny Nastor: The next point of doing your research seems really, really basic, but I screwed this up early on in my interviewing career, which is pronouncing somebody’s name incorrectly. Either the first name, which usually doesn’t seem to be the case, but often times a last name. I don’t do intros while the guest is there, but when I do the intro after the fact, I don’t want the person to come back later and be like, “Wow, you completely mispronounced my last name wrong.”

I’ve done that before, and it’s embarrassing. It’s really a discredit to you as a showrunner. Now, I literally go to a TEDx Talk or some video interview. I don’t know why. For some reason, this just takes me to video when I want to see somebody pronounce somebody else’s name. Then I literally have a spot now on my information sheet for the interviews where I actually phonetically write out last names.

This seems small, but these are the tiny little things, to me, that really show and step you up as a professional interviewer.

Read Whatever Guests Are Currently Trying to Promote (Books, Blogs, Et Cetera)

Jonny Nastor: The last step of doing your research is to read their book or read their blog, whatever work they’re trying to promote right now. We discussed this in the last part of the mini course. You’re looking for people at opportune times to be on your show because they’re more likely to want to. We are selfish in that way–in the fact that, if I have something to promote, I’m more likely to want to go onto more shows.

If I do have something to promote, and it’s my new book, take the time to read it. When I say, “Read the book,” I don’t mean you have to literally read every single page. But don’t read the intro, and then don’t try and make it like, “Oh, I read the book,” and quote something from my intro of my book. It’s kind of like, “Well, you read the intro–probably 20 minutes ago.”

Be a little classier. Maybe read chapter three or chapter four. Look through a table of contents. Look for parts of the book that would fit into your conversation, and go through those parts of the book. It’s really, really, really a worthy endeavor, and this person is taking the time to come on so that they can talk and provide value to your listener, also so that they can hopefully promote their product, their book, or their blog.

It’s your job now to make sure you’ve taken the time to have a reasonable, good grasp–at least in a reasonable amount of depth–of that work, that product, or that book, whatever it happens to be. Don’t skip this step. Don’t, “Well, I don’t read books, so that’s it.” Find a way, or else do solo shows. It’s really, really essential. It really is.

I’ve had guests where they’ll want to weave the book into the conversation, which sometimes doesn’t always work for the conversation you’re trying to do, but also, at the same time, when they’re doing it, you need to be able to respond, not just ask a question that doesn’t make sense, and they’re like, “Well, that was the intro to the book. Did you not read it?” And it’s like, “I sent you a copy.” Just do it. It seems obvious, again, like pronouncing their name right, but make sure you take this step. This is your job.

Your job, as an engaging podcast interviewer, it’s not just the interview. It’s really the work leading up to it that allows you to … those interviewers that just want to step on the toes of the guest where we’re always interrupting, asking another question, or asking a follow-up question that almost doesn’t need to be asked because it’s been answered 1,000 other places before, you need to go to those places beforehand, so you know this.

That’s where you get to the depth quickly because you don’t have to scratch all the surface stuff. You already know the surface. Your guest knows the surface stuff. Do this work beforehand, and it will pay off immensely when you get to the engaging interview.

An Example of Well-Executed Research: Sonia Thompson’s Virtual Summit Interviews

Jerod Morris: I just wanted to add to this. I had the good pleasure of doing a case study with Sonia Thompson inside of Digital Commerce Academy. Sonia, of course, is one of our students, Jonny, inside The Showrunner Podcasting Course as well, runs a successful show, and she launched a virtual summit.

As part of the virtual summit, she did 38 interviews. When we were talking about her experience doing these interviews, this was one of the key elements that she highlighted was really how much she prepared for the interviews by reading people’s books, by reading their blogs, and really trying to dig deep and ask the kind of questions that other people who follow these folks haven’t heard asked before.

That’s an obvious benefit of it. Let’s say if this person has been a guest on 15 or 20 other shows, chances are their fans have listened to some of those shows ,and you want some of those people listening to your show. What can you give them that’s new?

The thing that really struck me when Sonia talked about this was how much she felt it made the person she was interviewing be more engaged because she was asking questions that they didn’t usually get asked. A lot of times, people go on these interviews and, like you said, they want to weave in the book, or they have talking points.

Some of that you want to allow to happen, but you also want to ask them some deeper questions, allow them to bring up material that they don’t often get to talk about or stories that they don’t often get to share. When you can ask those questions, it shows that you’ve done your homework. You have more credibility, and you can get a more engaged guest with your show.

I know when Sonia interviewed me for that virtual summit, she asked me some questions that no one else has ever asked me. I was really impressed with the research, and it made me get into it more.

Again, as we’re talking about this as a performance, as entertainment, that’s so much better when you have someone leaning in, leaning forward, really into it, as opposed to just sitting back and giving their rote responses. You can really bring that out of people when you do your research and ask them the kind of questions that not everybody asks.

Step 2 of Giving the Best Performance Possible: Set Your Guest Up to Be Awesome

Jonny Nastor: Yeah. Very well said. This leads us, in a very nice way, into step number two, which is setting up your guest to be awesome. Doing that research, and as Jerod just said with Sonia’s example, is to ask engaging questions based on your research. That sets your guests up to be awesome because now they’re engaged. They can give a better performance.

Brief Your Guests with a Pre-Call

Jonny Nastor: Also, to set up a guest to be awesome is to brief them. This is the pre-call, right as you lead up to it. Mine is really, really short, but it gives the guest so there’s no grey area as to what they should be doing. People are always wondering, “Should I give 10 minute answers to things? Should I give one minute answers to things?” They need to know that just to be comfortable.

It takes me one to three minutes to brief my guests beforehand. We’ve scheduled a half an hour appointment, and I want to watch their time. If I say a half hour, it’s going to be a half hour.

I just briefly tell them, “Okay, the interview lasts 20 to 25 minutes. It’s completely about yourself, so there’s no wrong answers. Please, when I ask you a question about what you do, don’t tell me what people should do. Tell me what you do. Stories are great. Go as far as you want to. Don’t worry about getting too far off-topic because I’ve done this now, luckily, a lot of times, and I can rein you back in as I see necessary to take the conversation where I feel it needs to go. Your job as the guest is to just be free and to take it wherever you want. I will get into the conversation when I need to. Don’t worry about me. You just do it.”

You can just feel them like, “Oh, good.” Now, they’re ready. They’re ready to do a good performance for your audience–which is all they’re there for. It’s a really big waste of time for them, for you, and for your audience if they can’t perform, they feel like they’re performing for the wrong audience, or they’re giving a completely different performance than you are used to or that then really works for your format of a show. So quickly tell them that.

As with everything else, just be brief. Make it so that the guest knows what to expect, but then also that you’re respecting their time and that you’re not just telling them how a podcast works. They’ve probably been on podcasts. Just cover it. Chris Brogan did a great article about that, he’s a guest on hundreds of podcasts, and the things that really annoy him about podcast interviewers. But this brief is a really good one to really stick to and just tell them what to expect.

Don’t Start with ‘Tell Me More About Yourself’

Jonny Nastor: The second step is, if you do a proper intro, if you do an intro separate from the interview, which I think 99.9 percent of interview-based shows do–you do an intro to your guest leading up to the interview, all completely based on your research from the previous step–then there’s no need to start with that first question that also 99 percent of interviews start with, which is, “Can you tell me a little bit about yourself?”

We just finished a five-minute intro about this person before the interview explaining all this stuff about the guest, now you’re going to ask them. Speaking from my own experience and speaking to a lot of people I know that do interviews, the least favorite part of the conversation is always that, “Tell me about yourself.” It’s not a good way to warm your guest up.

Most of us don’t really like talking just about our pasts and what we did. We like talking about ourselves in an engaging conversation with the interviewer. When it’s just cold start–and lots of your guests will be a little bit uptight and nervous at the very beginning, and the pre-call helps–but then to just go straight into, “Okay, now give me a three-minute monologue. Make it good, and warm my audience up.” It’s not the best way to do it.

The way I’ve just always done this is, when I want to do the pre-call, then I quickly go over my intro points, the things I have written down from my research stage. Like, “You worked here. You did this. You did this based on LinkedIn, and then you also are promoting this book, which is available on this day.” It just allows the guest to tell you that stuff then, so you don’t get any of it wrong in the intro later. You don’t have to rehash it during the conversation.

Do an Audio Test During the Pre-Call

Jonny Nastor: Then the last part of setting your guest up to be awesome is, during this whole pre-section, it allows us to do an audio test. I don’t tell the guest I’m doing an audio test, but we are talking and having a casual conversation for a few minutes while I set her up to know what to expect. I can tell if there are issues.

If her mic is popping or if she needs headphones because there’s an echo, then I know this is happening. I don’t want them self-conscious about it, so I just, once, if it happens, if there’s an issue, then I’ll tell them about it. Otherwise, I just know confidently that we’ve just spent two and a half minutes talking. Everything’s great. We’re good to roll.

That also sets my guest up to be awesome because it doesn’t interrupt the flow of the conversation. I find there’s nothing worse than, you’re eight minutes into it, they’re giving you this great response, and all of a sudden this issue starts happening. You want to interrupt them, but you don’t want to interrupt them. Then you have to interrupt them. You got to try and bring that response of your guest, and she’s got to try and cut in halfway and just keep going with the answer.

We all know that doesn’t work very well. This pre-call, setting your guest up, allows that time to do that test. I just trust that if it works for two or three minutes, it’s solid, they’ve got their headphones now, and their mic is good, then we’re good to go.

Should You Send Guests the Questions in Advance?

Jerod Morris: Jonny, one of the most oft-asked questions when it comes to planning interviews is, do you send the guest the questions ahead of time? In fact, I think we covered this a little bit in lesson one of this mini course, but this is also a pertinent time to discuss it.

People can go both ways on this. You talk about setting up your guest to be awesome, sending them the questions ahead of time so that they can prepare, have a look at them. You could certainly argue that would set them up to be awesome.

I know me, personally, I do like getting the questions ahead of time when I’m going to be interviewed. A lot of times, as someone being interviewed, I don’t have time to go listen ahead of time to all of the shows that are going to interview me as much as I’d like to. I don’t necessarily know what their normal questions are, what to prepare for. How do you handle that?

Jonny Nastor: That’s a great question. We did go over this in the first section, which was you can send them to your interview format page, which can have some questions. Also, I suggested having that intro email that has up to three questions in it that you will possibly cover. Again, depending on how loose you want to be with the conversation, you might not get to all of those, but it is a good thing.

Actually, it’s great that you mention this because I didn’t mention that, in my pre-call, I’ll say, “So whenever we’re ready. I’m just going to have a drink of coffee, and then when you tell me you’re ready, I’ll hit record. I’ll literally just say hi to you, and then we’re going to jump straight into the first big question.” That, to me, sets it up.

Otherwise if I don’t say that, I found that I would just be like, “Okay, welcome back to Hack the Entrepreneur.” Now, the guest is used to a lot of other podcasts, and they just want to talk about the weather and all this stuff. Like, “Dude, what are we doing? Let’s get to the conversation. The intro’s done,” kind of thing.

When I say, “We’ll just jump into the first big question,” I’m going to say 20 percent of my guests, at that point, are like, “Oh, I didn’t see that. What’s that first big question?” I tell them, and they’re like, “Can you give me a minute?” Then all of the sudden they’re like, “Yeah, let’s do this.” You can just feel them confident and just ready to go.

The other 80 percent of the people, they’ve either read it, or they just don’t want to know. Lots of people just don’t want to know the questions. They feel like they work better off the cuff. I think you should give people those options. To me, that’s really pre-call prep. If you’re going to jump into a first question, then you should at least tell them that’s what you’re doing, and then they can choose whatever’s going to make them the feel the best and the most confident at that point.

Jerod Morris: Yeah. Very good.

Step 3 of Giving the Best Performance Possible: Work Backwards

Jonny Nastor: Cool. All right. The last step of this is to work backwards. This is planning out what you want to happen with the conversation. Thinking about the ending, mostly because there’s nothing worse, I feel, than going through an awesome interview and then all of a sudden you realize, “Oh, I should have quit this six minutes ago.” Then you’re like, “Okay, I can just go back and edit it.” You lose flows and things.

To me, I want to know where I want to end. It’s why I actually end at the exact same question now, and I start at the same question. Then questions flow and really can go way off-topic at times now during my conversation, but I know exactly where I want to end. That ending takes me back through, and it allows me to plan out where I want to get this conversation to.

It makes sure, to me, that the conversation ends on the highest note possible. I don’t want people to be thinking at 10 minutes in like, “Wow, this is really awesome,” and then 20 minutes of just, “I’m not sure what happened.” You forget those really awesome parts otherwise.

Know the Transformation You Want Your Listener to Have

Jonny Nastor: If you can end on a bang, which is that really big thing, which takes us to step two, but I’m going to call that the transformation that you want your listener to have. What is it you want your listener to really, really grasp from this conversation? To me, that has to be that end point. Then you got to think, “Okay, I’m going to give myself 40 minutes for this interview, and I know that I want to end … ”

With Hack the Entrepreneur, I end on this entrepreneurial gap–which is literally stopping for a moment right now and thinking back across your career and how you feel about it. No looking forward at this point. Then I take them through projects they’ve done, and projects they want to do, through just their working and their habits, back to the beginning, what’s the thing you do right now. It’s this cool transformation.

You can hear the guest go through it, and at the end they’re like, “Wow, that question … ” Then they have to think. It also really encourages them, and they get to end on this good note, too. That feeling that the guest has at that point, to me, is the transformation that I want my listener to have.

I used to be against this idea of the transformation. I used to think it was woo-woo or something, if you want, but it’s really, really, really an imperative thing. It’s not just things you need to check off or something. This is literally what it is you’re trying to get your listener to do through their head or something.

This transformation, that’s what they want. That’s what’s going to keep people coming back for more. Find that point. What is it? If you’re teaching them about anything … you know your audience of one. We’ve talked about this. You know who they are. You know what their hurdles are, what their struggles are, all those things. What keeps them up at night?

Then, you also need to know where it is they want to be. That’s the transformation. In these conversations, you need to help and allow your guest to take your audience through that transformation. You need to know that, and then you need to work back.

Use Checkpoints to Stay on Track

Jonny Nastor: Then the last part of this working backwards is, as I just said with Hack the Entrepreneur, is to have those checkpoints. You know where you want the transformation. You know where you need to end. Then you need to work back to that first question. That first question shouldn’t be, “Tell me a bit about yourself,” because that’s your intro. Then it’s going to be this beginning and this ending.

You can get as loose and amorphous as you want within this process, but I find that–to get from point A to that very last point, say, D, if that’s where you want it to be at the end–you should have some checkpoints where in some sort of way you can bring it back.

This is how, when I give my guests the pre-call and I say, “You go as far as you want to go into stories. Go off-topic as far as you think. I don’t want you second-guessing as you’re talking because I want it just coming out of you. That’s where the good conversation comes from. Don’t worry. I’ll bring you back onto topic.”

I can say this confidently because I have the four parts. I know we’re talking about entrepreneurship. We’re talking about business. We’re talking about projects. I know that we’re never going to get so far off-topic that I can’t all of the sudden, “Okay, now let’s talk habits.” I know that if this conversation goes this way, “Okay now let’s move on to projects.” I know that projects is the final step before we get to that very last ending point that I want to be because that’s now what they’ve accomplished through all these projects.

It’s your road map of the conversation. You don’t need questions, necessarily, that are pre-written because you want it to be loose and forming, but you want these checkpoints. Otherwise, you’re going to be at 38 minutes, you’re like, “I only wanted to go 30 minutes,” and you still have to get to this last question, which is the transformation point. Then you might just start missing the transformation point.

If you have that road-mapped out, it’s going to take time, but you’ll be able to … every 10 minutes or something, you’ll be like, “Okay, if I get to this next checkpoint and this next checkpoint, this next checkpoint, at 40 minutes … ” Bang on almost, you’ll be at that transformation question, and you’ll be wrapping up.

The conversations will go an infinite number of places within that. But at the same time, every single time, your listener is going to get what you told them they’re going to get, which is that transformation.

Why Being a Good Listener Helps You Keep Track of Checkpoints and Be Ready with the Right Questions

Jerod Morris: Here’s a question that transitions us into the third part of this, but I love this. You talk about working backwards. You’ve got your end in mind. You, in particular, start with that same first question, and then you’ve got these checkpoints as you go. You talked about how you don’t necessarily want all of the questions in the middle to be pre-written, but what’s your strategy for coming up with questions as we go?

I think a lot of people who are interviewing have that anxiety of, “This person’s going to stop talking at some point, and I need to have something to say.” For some people, that’s having a list of pre-written questions ready to go, but obviously, the best conversations you’re really able to live in the moment of the conversation, respond and react to them.

How do you make sure that you’re keeping track of the checkpoints, number one, and that, when the conversation does come back to you, that you have the right question, the right words, to get it on the track that you want to go and also get out of the person that you’re interviewing what you want to get out of them?

Jonny Nastor: I listen. You have to. If you are just so focused on, like you say, having this pre-list of questions, then we end up not listening. Somebody will give a brilliant answer that is going somewhere. Whether they want to or not, or consciously or not, it naturally goes that way, and it feels like, “Yeah, we should go deeper into this.” You need to be able to run with that because you’re listening and engaging.

It’s, again, a human conversation. Unfortunately, we have these computer screens in our way, but that’s it. They’re literally sitting on the other side of your desk having a conversation with you. If a death in the family comes up or something traumatic like that, for you just to skip over it and say, “Well, what are your three habits in the morning?” It’s pretty inhumane.

Jerod Morris: Callous.

Jonny Nastor: Exactly. That’s going to completely, that’s it, you did not set your guest up to be awesome at that point. I actually struggled with that yesterday with a conversation because I knew where I wanted to go, but it was like, “Wow … ” We had to go into that, but at the same time, I don’t want to go so far off.

My audience doesn’t want to all of a sudden hear us talk about the death of your mother for the next 25 minutes. To ignore it is just harsh. It’s callous. You can’t do it. It’s going to be off-putting for your guest, and it’s going to be off-putting for your listener.

At the same time, when you know where you’re heading … I’ve done this so many times now, but if I know that I’m heading to a next checkpoint, at least from listening to the conversation, I know in the back of my head that, “Okay, I need to get to this next checkpoint sometime in the next five to six minutes.” My follow-up question in our conversation, I can push it that direction so that it’s not like, “Okay,” completely abrupt, “We’re talking about death in a family to, now, can you tell me how to market your product?” It’s not going to be like that.

This takes practice, but this takes research and takes knowing. You typically don’t get sideswiped by something completely off the radar in the conversation because you’ve done your research, but then being comfortable with taking it in directions you need it to go but with the conversation.

I know that’s not really an answer. The answer itself for doing this working backwards is really knowing that exists and knowing that those checkpoints are there. Doesn’t mean you can necessarily hit them every single conversation. It doesn’t mean that you should. But I think it really did actually help … I don’t think–I know that it helped me structure and just get a lot better and more comfortable in my conversations, which comes out to the listener and allows you to grow as an interviewer.

Of course, there’s going to be endless special cases and certain things that are going to happen in conversations that you can’t control. That’s the cool part of it. You should nourish those times when they come. But I really do think that having those points and knowing, they become natural to you. They’ll evolve over time as you’ll get to know your audience better or your audience evolves, whatever happens.

It’s not just a loose conversation about anything mostly because your audience is there for a specific reason and to get this certain transformation out of you. So me just all of a sudden talking about baseball because my guest, she played baseball with her son over the weekend, and they had a lot of fun, if I all of the sudden went for the next 30 minutes about the rules of baseball, it would be a natural flow possibly of a conversation over a beer. But I don’t want to hear that recorded and put out to my listeners who want to learn how to start businesses.

Jerod Morris: Yeah. That’s why a great interview is a combination of art of science. It is both.

Jonny Nastor: That’s exactly the best summary of it right there. It is. It’s that combination. To ignore the science and not have it in place beforehand and just go with the art. Art usually even has to just follow the rules of art to be good art. You have to know the rules before you can break them. That’s the process.

A Quick Review of Lesson 2

Jerod Morris: Yep. In summation here for how to plan engaging podcast interviews, you want to do your research. Apps like the Charlie App will help. Certainly understanding how to pronounce folks’ names is extremely important. Then do your research in terms of reading their book, reading their blog, any work that you can find to make sure that you can ask good questions–good for your audience and good to keep the person that you’re interviewing engaged.

Number two is set your guests up to be awesome. Make sure that you brief them, as Jonny described. If you’re going to do a proper intro, remember that you don’t need to start with the old, “Tell me a little bit about yourself.” Verify your intro point with the guest. Let them customize it. Then this also gives them a few minutes to do an audio test, which is nice, without them noticing, which is cool.

Step number three, then, and really the crux of this, is working backwards. Thinking about the ending first and then understanding what transformation you want your listeners to have from beginning to that end, and then having check in points that allow you to keep the conversation moving forward in the way that it needs to move forward.

Jonny and Jerod’s Self-Assessment of the Delivery of Lesson 2 and a Callout for Listener Feedback

Jonny Nastor: Excellent.

Jerod Morris: Good work, Jonny.

Jonny Nastor: Thanks, man. I think we did it.

Jerod Morris: I think we did it. Now, we have lesson three coming up in How to Book, Plan, and Execute Engaging Podcast Interviews, which will come in two weeks. Next week, we have the second lesson in my mini course on differentiating your show.

Jonny Nastor: This is fun.

Jerod Morris: This is fun. I really like this format. This is cool.

Jonny Nastor: Yeah. It’s really forcing me to really think about the episodes beforehand. It would be interesting to hear from you out there listening what the difference is as the listener for the really structured, as we said, this 3-3-3 outline we’re following compared to, say, three or four episodes ago where it was just us with a couple ideas and then we could just loosely talk.

Maybe it’s a cool changeup. Maybe it’s just a better format. Maybe you just like it when we’re loose. I don’t know. It’d be pretty cool to hear. Let us know.

Jerod Morris: Yeah, it would. Let us know on Twitter, @JerodMorris, @JonNastor. We would love to know. With that said, let’s do a podcast recommendation.

Jonny Nastor: Let’s do it.

Podcast Recommendations of the Week

Jerod Morris: I will kick this off. Jonny, I have a really interesting recommendation. It’s a show called Beautiful/Anonymous on the Earwolf Network. The basic premise behind the show is it’s one phone call. It’s an hour long, and there are no names. Random people call this guy Chris, and the only rule is that he can’t hang up for the first hour. They can hang up any time they want to, but he can’t hang up. They just talk.

What’s interesting about this is, he’s doing an interview, but he can’t really work backwards because he doesn’t know these people. He doesn’t know really where he wants to go or necessarily what transformation can happen. He just knows that he wants to have a great conversation with these people.

I recommend this show for two reasons. Number one, it’s just interesting to just hear these random people and their random stories, and to hear how the conversations evolve. They evolve in ways that you really wouldn’t expect. But also to study it in terms of, how do you come up with those next questions?

The secret that you’ll learn from listening to this show is about listening, like you talked about, Jonny. That’s really what Chris, the host of the show, does so well–he listens. That allows him then, when the spotlight is back on him to ask a question, to ask a really good question. It doesn’t feel like an interview so much as just a conversation.

Usually, the best interviews do feel like that. This is good, appropriate listening for this topic and just if you want a fun, new, unique show. We’re all about podcasts that are out there trying new things and coming up with unique ideas. This one fits both bills. It’s called Beautiful/Anonymous. You search for that in iTunes or anywhere else, you will find it. Very good show.

Jonny Nastor: Excellent. Two episodes in a row now, but I’m going to keep it in the family this time. This is a great podcast, co-hosted by my co-host, The Digital Entrepreneur. You can find that at The Digital Entrepreneur is Jerod Morris and Brian Clark, CEO of Rainmaker Digital. You guys did an excellent episode. I cannot remember the guest, but luckily, you were on the show. The episode was called Secrets of a Six-Figure Online Course Builder. It was an interview with …

Jerod Morris: Danny Margulies.

Jonny Nastor: Nice, with Danny Margulies. That is my recommendation, The Digital Entrepreneur. If you want a specific episode, it is Secrets of a Six-Figure Online Course Builder.

Jerod Morris: Yes, we would love to have you listen to The Digital Entrepreneur, which I’m having a lot of fun doing. With that said, Jonny, I think it is time to wrap up. It is now my turn to go prepare the next episode, so I shall turn my attention to that.

How to Take Your Showrunning to the Next Level

Jerod Morris: But you, dear Showrunner listener, turn your attention toward Showrunner.FM, the URL. That is where you can go and join The Showrunner. You can get our weekly newsletter if you’re not getting it already. It includes announcements of free public events, like the public Showrunner Huddle that we had last week to answer folks’ questions, which we always enjoy doing. Plus, we give you a recap and a summary of that week’s Showrunner episode.

Then, the world’s greatest podcast email newsletter section, I’m just going to make that claim right now, it is our ‘we highly recommend’ section that you don’t want to miss as we always try to find something thought-provoking, interesting, helpful, useful, to help you take your showrunning to the next level.

You don’t want to miss it. We alternate. One week you get Jonny’s perspective. Another week you get my perspective, and we go back and forth. We try and really give you good stuff in that section. Showrunner.FM–join the email list. Get that and a whole lot more when you join.

Jonny Nastor: That was a call to action and a half. I liked it. It was good. It was well done.

Jerod Morris: Thank you.

Jonny Nastor: Yeah, it’s been fun. We did part two of the mini course. We have a call to action. We have a podcast recommendation. I think that’s it.

Jerod Morris: I think that’s it.

Jonny Nastor: Let’s do it.

Jerod Morris: It’s time for us to wrap up. Thanks for being here.

Jonny Nastor: It’s been a blast.

Jerod Morris: We’ll talk to you all next week. Why are we talking over each other all of a sudden?

Jonny Nastor: I’m not sure. Yeah, we just keep trying to end it. I apologize, Toby.

Jerod Morris: Sorry, Toby. We’ll talk to you all later.

Jonny Nastor: Take care.