Crafting Your Podcast’s Point of View – Jeremy Shere – Creating The Greatest Show – Episode # 041

by | May 12, 2023 | Creating The Greatest Show, Hosting a Podcast, Podcast Framework, Prep Call

Our next guest is an entrepreneur, writer, creator, and marketer that has been podcasting since 2017. Jeremy Shere hosts both The B2B Content Show and The Pod Shop and is the Founder & CEO of Connversa. Jeremy shares why your show needs a strong point of view to stick out, the case for having a podcast prep call, and how to guide a podcast conversation.


  • As the host of an interview podcast, you should know that it takes time and lots of practice to learn the “art of the interview”. Consider your own limitations and perspective when beginning each conversation so it can have a natural flow and feel less scripted.
  • The best podcasts are able to stick out because they have a strong and distinct point of view on a particular topic or field. That perspective which the show is built around elevates it beyond the sea of podcasts that are simply two people discussing an idea.
  • Don’t make appearing on your podcast feel like a chore for your guest by sending them a form to fill out. A prep call between the guest and host is a much more personal way to get prepared before the podcast recording.
  • An effective prep call should be friendly and relaxed but also have a pinch of structure. You should discuss the idea you want to start the show with, but don’t go too far into it on the prep, save the good stuff for the recording!
  • As the host, your goal on the prep call is to build rapport with your guests and ensure they’re prepared and comfortable with coming on the show. Without scripting the whole show, you can discuss where you and the guest would like the conversation to go.
  • Podcast hosts need to listen to both the literal words their guests are saying as well as the flow of the conversation and how it is unfolding. Hosts have to know when a tangent is worth going down and when they need to pull their guests back to the topic at hand.
  • It’s OK to disagree with your guest, but make sure you do it respectfully and organically. If you come prepared with “gotcha” questions, the podcast will become contentious and you’ll lose any chance of building a strong relationship with your guest.

READ MORE: Why You Need a Prep Call for Your Podcast

Quote of the Show

“I think every podcast host will admit they used to suck at it and now they’ve gotten better if they’ve kept up with it.”

– Jeremy Shere

Connect with Jeremy:

Shout Outs: 

  • Natasha Miller
  • Mark Evans

Ways to Tune In:



Casey Cheshire: right. I hit the button. I hit the button. This has begun the adventure. It’s underway and we can’t turn it back. We can’t turn back the hands of time. So let me introduce my guest today. I. We’ve already had an a podcast worth of conversation already that you didn’t get to hear, so we thought maybe we’ll hit record so you can hear this part.

Man, what a great guy. I can’t wait to talk more about this thing that we all love podcasting with him. Who is he, Casey. Enough about your [00:01:00] feelings, more about the guest. He is an entrepreneur, a writer, a creator, a marketing leader, a thought leader. He has a PhD in philosophy, in English literature.

Let’s go. He’s been podcasting since 2017. Host of the B2B Content Show and the pod shop founder and c e O of Conversa, Jeremy Sheer. Welcome,

Jeremy Shere: sir. Thank you so much and what a wonderful introduction. I just wanna correct one thing. I’m not a marketing leader. I would never describe myself that way just because.

I interview Mark, like real marketing leaders on the B2B content show, so I can learn about marketing. Totally. But, I would, I am, I would never call myself that, although it’s very flattering that, that you said that. But out of just respect to all the people I’ve interviewed on that show, they’re the marketing leaders.

I’m just learning from them. That’s all.

Casey Cheshire: Man I feel the same way about everyone I talk to on this show and even on my marketing podcast. It’s amazing the people [00:02:00] we get to ch a chance to talk to and learn from. Yeah. Yeah, there, there’s some real wizards out there for sure. I dunno if you’d do this, but I call myself like a caveman with a hammer.

I’m not even good with hammers, I’m the one hitting my thumb with it, hey, let me get to this first question. I can’t wait to dive into your thoughts and your answer on this. Yeah. Jeremy, pull back the curtain for us on your show and share your most important strategy for a great interview podcast.

Jeremy Shere: Okay, so maybe let me tell you about the show just a little bit, just to give a little context. Sure. Because I think, every show is a little bit different. And what constitutes a great interview will depend at least partly on what the show is about. So the B2B content show, like that’s, you mentioned this other show I have called the Pod Shop, but the main one I do and the one that’s been going longest is called the B2B Content Show.

All about B2B content marketing [00:03:00] and where, as I mentioned just before, I’m interviewing marketing leaders, heads of content, VPs of marketing, that sort of thing. Yeah. And so this is also a case where, as I just said, I am, the amateur. I am not a marketing leader. And so as the host of the show, that’s how I position myself.

Like I’m learning from you and I’m hoping that our audience will too. And I’m saying all this because I think that matters in terms of the quality of the show and the quality of the interviews I do. So I think that one really obviously one super important. Element of any interview show and what’s gonna make or break it?

It’s honestly hard to pinpoint it down to just one thing. Sure. But I’ll do my best. So I know,

Casey Cheshire: unfortunately, obviously gunpoint

Jeremy Shere: to do that. Yeah. Virtual gunpoint. [00:04:00] One is, one major factor is the host and how good the host is at doing the interview. And I think in order to do that, the host is, has to understand their own limitations and kind of the perspective that they’re coming from.

Because if you don’t that if the host doesn’t have a clear understanding of that, I think it’s just, it’s hard to develop the right kind of rapport with the guest and do an interview that actually just turns into a free flowing conversation. And less of a series of questions that are answered.

And I find that, ho be becoming a good host like the art of the interview. It’s something that you learn over time with practice, and I think every podcast host. [00:05:00] Will admit if pushed enough that, they used to suck at it and now they’ve gotten better if they’ve kept up with it.

And when you listen back to some of your earlier episodes, yeah. You’re like, wow, I’ve come a long way. Or I’m just much better at this. And the episodes sound a lot better because I. I’ve learned, the trips the, sorry, the tricks and the techniques and all that stuff. So I think that’s one key.

If it’s you, it’s your show, then you need to get it, dedicate yourself to learning the art and science of how to interview people. And if you’re producing a show, say for someone else, like we do at Conversa for a company or whatever, Then you need to pay quite a bit of attention to who’s the host gonna be, what kind of training and coaching do they need?

Where are they starting from? If they’re starting from zero, what kind of natural abilities do they have and what do we need to improve on? [00:06:00] And I think you can’t, in a way that’s just, of course, pretty obvious, but I think you it’s, you can’t really talk about it too much. The quality of a host can just make or break an interview show.

Casey Cheshire: When really focusing on the ho, it’s like the quarterback, right? To throw in a random sports analogy. Yeah. My beloved Patriots did so well, and then Tom Brady goes to Florida and then who, I don’t even know what we’re, I don’t even watch the games lately. So sometimes there are pivotal roles and in this case, by it’s very nature, the host is that role.

I heard you say something. The host needs to have some sort of sense of where the guest is coming from. What did you mean by that?

Jeremy Shere: So the guest’s point of view. Point of view, yeah. I think is the best way to, to put it. And I think the host has to have a clearer understanding of [00:07:00] their own point of view too.

I think one of the key the keys to success of any podcast, including an interview show, is that it needs to have a strong point of view. There are so many shows that are just two people talking about stuff, or if it’s a B2B podcast, two people discussing important trends in the industry.

Okay. Which is fine, but I think the best shows. What makes them stand out? One thing that makes them stand out is that they have a very distinct point of view.

Casey Cheshire: The show itself or the host does,

Jeremy Shere: or both? The both because I think they’re, those are inseparable. As the host you’re the one articulating that point of view and embodying it, but that your whole show is built around.

A particular take on whatever your show is about, right? Yeah. And then the great content comes when you bring on guests that they might [00:08:00] align with that point of view, or sometimes even better, they might not, they were gonna bring in a different point of view that’s not necessarily opposed to the point of view of the show directly opposed, but it’s different enough that you’re chopping it up and not always just agreeing.

The exchanges are not always oh, that’s so true. That’s a great point. It might be like let me push back on that a little bit. What about this? Or you said this. How do you know that it’s I think that’s where some of the drama intention can come in an interview show.

So cool. And so another element here that I think is really important. So number one is, Having just the best host that you can have or whoever the host is, having that person dedicated to improving episode by episode. And then the other another important element is doing prep calls with guests.

Okay. I’m a big advocate for that. [00:09:00] Okay. And there was a post on LinkedIn just yesterday about this. Not my post, some, someone else who I don’t know, but I participated in the conversation and the question was do you do prep calls or not? Are they important or, and this person’s point was they’re peeved when instead of a proper prep call, like we, like you and I did for this, like we did Yeah.

For this episode, right? Yeah. It’s you, someone just sends you like Like a Google form with a bunch of questions that you have to fill out the form’s


Casey Cheshire: than a PDF or at least a pdf. It’s but form. Come fill out my form and be on my show. Yeah.

Jeremy Shere: It’s like here’s some extra work for you to do.

That’s just like a chore. As opposed to the prep call Witch, you’re getting to talk to a real person and have a real conversation and. If, again, if, and it should be the host doing the prep call and if the host is [00:10:00] good at that, and there’s I think there’s a whole kind of art and science to doing the prep call as well.

But again, it should be friendly, relaxed, you’re trying to build rapport. You’ll often start talking about the topic and even getting into it in the way that you’re going to, in the actual in the actual interview. Although I think part of the job of the host there is to not go too far down that road.

You don’t want to, shoot all your bullets in the prep call. Oh, yeah. But to, what I really value about these, about prepping with a guest is you come in, maybe with some idea of what you want to talk about. Or not, often I don’t, I’m like I want to let’s discuss ideas. Yeah.

But the whole point is whether you have some starting idea or not to, once you do have some idea, which is usually fairly broad to explore with the guest. What’s the beating heart of this topic? What are the main things [00:11:00] that we want to hit? And that’s gonna really depend. You could bring in, for if you had three different guests lined up, they might all have different ways of answering that, different things that they wanna focus on, which is good.

That means, you could, in, in my podcast, the B2B content show we’ve done Multiple episodes on kind of the same topic, roughly, but they’re all very different. Because we’re focusing on different things or the particular guest has a particular take on it, right? A particular point of view on it.

And so I wanna learn what that point of view is, and then when we actually go to record the interview, I’ve written questions that align with that point of view that take that into consideration. And I feel prepared as the host to guide and shape the discussion in a way that’s gonna be the most relevant to the audience.

That’s gonna get right to the heart of the most interesting, engaging [00:12:00] part of this topic. And so it’s gonna be efficient in that way, while all at the same time allowing the conversation to take interesting twists and turns that I didn’t anticipate, but at least I’m starting from somewhere very solid and that way another, as a host, and I think this is another crucial skill that a host has needs to develop, is no matter how much you plan, during that prep call when you actually hit record, You’re never quite exactly sure how the conversation’s gonna unspool.

And a host has to be good at listening on different levels. On the one hand, just listening, on the most straightforward level, just what is the guest basically saying? And so you can be prepared to respond to it and ask follow up questions, but also listening for. Are we sticking to what we had [00:13:00] planned to say or the guest seems to be going off on a bit of a tangent here. Yeah. That’s interesting. And it’s your job as the host in real time to make the call like, okay, do I need to reorient this back to what we had discussed? Or is this tangent actually even more interesting than what we discussed?

And I’m, we’re gonna roll with it and let it go. Yeah. As you’re listening to the person talk. Yeah. So you have to be thinking about that on the one hand, while you’re also processing just what they’re saying to you on the other hand. So you have to keep this all in your head as it’s happening in real time, and then make those judgment calls throughout the course of the interview.

Yeah. I think that’s another, crucial skill for a host to have, because at that point the guest is just talking, they’re in the flow. Yeah they probably don’t even realize that they’re going off on what, you’re considering a tangent, but maybe it’s a fruitful tangent [00:14:00] or maybe not.

Casey Cheshire: And. This is so cool. And this is what I like about this show, is it’s so meta, right? Not to be confused with Facebook and armless, emojis running around a virtual universe. So we actually had this exact thing happen that you’re describing just now with us. So we were chatting about the ideal hosts and the distinct point of view and agreeing, and there’s some things I’m gonna circle back to at some point because I wanna dive into that.

Yeah. And then came up the topic of prep calls, and then in my mind it was, Man, I really wanna talk about disagreeing with your guests. I wanted these other things that, but you know what, you were on a roll and you were really explaining some good stuff. Don’t wanna show all the bullets on prep call, how important it is.

And I agree with you. Prep call is I. Vital it is the thing. And so I want, wanted to hear your topic and take on that. So I let us just run with it and what’s great is because I did that, we’re able to have this real example and then you were able to talk [00:15:00] about how a host needs to allow that to happen.

And because I was able to allow that to happen, you were able to make a teaching moment and then we were able to make this whole thing meta.

Jeremy Shere: There. There you go. Which is a testament. Wow. Yeah. Which is a testament to your skill as a podcast host. Oh, cool. Thank you.

Casey Cheshire: But I love that it all happened, in real time, so we can demonstrate on a show just as much as it, so talk to me about, Cor corralling. Let’s do cor corralling your guest back on topic if Yeah, maybe they weren’t off until like frozen yogurt land. But then after that, let’s talk about disagreeing.

Okay? Sure. So corralling a guest, right?

Jeremy Shere: Kinda yeah. Roughing ’em and bringing ’em back. I think that, I think for less experienced podcast host or any kind of interviewer, this can be an uncomfortable thing. Yeah, especially if the guest is someone like you [00:16:00] admire or someone who’s like a big deal in, at least in your mind.

I think there are different ways to do this. So one is if the guest is often a bit of a tangent, let it play out and then, one simple technique is to be like, wow. That’s really interesting. But I wanna circle back to, to, something we were talking about before.

That’s a simple way to Cut that tangent off, essentially okay, we’re done talking about that. Now let’s go back to our, the main thing that we actually are talking about. And, just to do it in that really straightforward way. I’ve done interviews before where, and this isn’t exactly going off on a tangent, although it could be, but it’s a slightly different problem that also requires corralling the guest.

Yeah, please. When a guest just won’t stop talking. Oh yeah, you had those.[00:17:00] Oh yeah. That’s not

Casey Cheshire: you. Not you by the way. Okay,

Jeremy Shere: But that’d be funny though. That’s happening right now. If it turns out that is me and at some point during this interview I’m just b blabbing, on and on, you might feel the need at some point to a little bit jump in and be like, Hey, can I jump in for a second here?

You said something. I wanna, that’s another thing you have to be able to do as a host, is you sometimes get guests that are just talkers. I’ve had interviews where people start talking before I’ve even asked a single question or even introduced them. Yeah. They just, as soon as we hit record, they’re just off and running.

I’m like, whoa. Okay. They just have a lot to say and again, you as the host, you have to judge when is, might be a good time for me to jump in here. Yeah. Because this is now going on a bit too long, we’ve design we’ve designated an hour for the interview, let’s say, or a [00:18:00] half hour, and I have, about five questions or whatever I want to get to.

We’re on question one and we’re 12 minutes in. Yeah. You’re also looking at the clock and you’re like, okay I, we, I need to jump in here a little bit and so what I do, And it’s pretty rare that this happens, but when I do, I just, I wait for a little bit of a pause. Maybe the person’s just taking a breath.

You’re right. And you just have to politely interrupt them. Yeah. And jump in and be like, Hey, can I, can I just wanna jump in here for a second. All this is super interesting. I wanna go back to something else you said, and then in that way, reorient things because for sure the guest is not aware.

Of what they’re doing. They’re not aware that they’re going on and on in a way that needs to be corralled. Yeah. They’re not gonna magically realize that you as the host have to do something about it. I love that

Casey Cheshire: we’re talking about this, right? This is like [00:19:00] the real side of podcasting, right?

Yeah. I mean there’s fluff and there’s all these other things to talk. Hey, how great it’s, but there are some just real personal challenges where you need to. Politely interrupt somebody because they’re being a blabbermouth. And I will say one of the things that you don’t wanna do you do need to do that at some point.

And I have made the mistake of not doing that. And then let them talk for it would feels like 20 minutes. And. And the worst thing that could happen is I I checked out, right? And I was like maybe I can check my email or something. Clearly I’m not involved in this conversation, so I’ll just let them go.

And it’s ah, that’s the worst thing to do is to abdicate control of the show and let them take, jump in. It’s your, show you your responsibility to get in there and fix things.

Jeremy Shere: Yeah, it’s a, it’s a delicate calculus, yeah. [00:20:00] On the one hand, you want the conversations typically to be unscripted free flowing.

You don’t wanna put in place too many parameters that narrow the, that, that make the guest feel self-conscious. Or too, that you’ve too narrowly defined the parameters. Because you want some of those tangents, like we were saying before, can be really good and fruitful.

Yeah. But on the other hand, you still want the final product to, to be coherent, cohesive, have a kind of through line so it’s not just all over the place. I’ve produced episodes for people where I’m thinking of one instance in particular. Of course, I won’t name names where. From the start, I could tell and I was just like producing, not, it was somebody else was the host.

They started in one place, but they just went all over and it was long. It was like a [00:21:00] 45 minute interview and it came out and I was like, they touched on eight different topics that are all loosely related, but it was just too much, it, it was just, It wasn’t coherent in the way that I prefer interviews to be, that I think interviews are at their best.

And again, it’s your job as the host to make that happen. Yeah, it’s your fault if it doesn’t, right? It’s not the guest’s fault. No matter how well you’ve prepared them, they’re gonna do what they’re gonna do, and you have to find ways to, while allowing it to be freeform and flowing and all that stuff at the same time, to be subtly shaping it.

And reigning stuff in just enough to give it that coherence without killing the, the spontaneity of it.

Casey Cheshire: And and you owe it to the guests too. I think half of us don’t wanna offend them, but it’s almost more offensive to let them be a lesser [00:22:00] version of themselves than to interrupt and bring out the best in them.

So really dive in there and get after it. And so I’d love to transition to, when you talk about disagreeing and having that strong point of view. Yeah. I remembered an experience where I was starting to have that same kinda like mental checkout. This isn’t a dialogue, this is person throwing something at me.

And then they mentioned something in the marketing world where they said, I think you should put a. I think you should get rid of all your forms in front of your content. And I’m a big marketing automation guy and maybe this we’ll have to like dot this topic against, to the marketing show, but I actually feel the opposite.

I’m like, content the hell out of it. Form the hell out of it, but don’t make them giant forms. Make them these little tiny little things you barely even notice. Your browser fills it out for you anyways. Make them very small and efficient is my take. The he to take, I had to take and it reinvigorated me.

Yeah. And I was suddenly [00:23:00] interested it again. And we had a little back and forth. It was friendly. And I think I might have convinced him, it, it was good though. And I feel to your point about, have a point of view, but talk to me about how you disagree with your guest. And you don’t make it like a show where it’s like a C N where you’re like pouncing on someone.

Oh, you’re a loser and actually you’re wrong and here’s what it really is. Yeah. How do you do that the right

Jeremy Shere: way? Yeah, great question. First of all, I think you just described very nicely what not to do. It’s, you’re not you’re not you’re not trying to get people like you’re not asking gotcha questions that they’re not prepared for or that put them in a very awkward position, right?

That’s just gonna destroy whatever relationship you’ve built. And it’s just uncomfortable, and I think, We’ve all seen enough of that on, in the media to, to have grown. Very tired of that kind of thing because it doesn’t result in good content often. Yeah. It’s just [00:24:00] contentious, but you don’t really learn anything.

It turns into an argument rather than a discussion. Yeah. I think the key to. To disagreeing or like having a real discussion from different points of view. Like your example about should you get content or not, right? Yeah, that’s a great topic and there are plenty of valid opinions on all sides of that debate, right?

So I think number one, the key is it needs to be organic. This shouldn’t be something that’s forced like you are. You’re deliberately taking an extreme point of view in order to disagree with a guest or something like that. I think that it needs to be organic. On the other hand, you might play devil’s advocate, but as long as you own it, be like, playing devil’s advocate here for a second.

Let me push back on that thing that you said. I like that. But I think it’s best when it’s organic and you really do say I have a different way of looking at that. And [00:25:00] I think the, as long as you keep it. I want in one way. I want to say polite, but that’s not exactly the word.

You want to keep it non-con, contentious, keep it from getting into an actual argument where you’re like, you’re trying to win. Your goal there is, you’re not trying to win an argument. You’re not necessarily trying to persuade the other person that you are Right. And they’re wrong.

That’s an argument. Yeah. A discussion where you’re, where you disagree. That’s where. You’re, I think actually that’s kind of conversation at its best. That’s interview at its best. That’s when both parties are open to exploring an idea together, batting it around, considering the other person’s point of view.

Yeah. And legitimately challenging their point of view[00:26:00] in, in, in a in a respectful and thoughtful way. Yeah. So in other words, not just. Attacking them, personally, or not just saying that’s stupid, or making it super political or something. But saying, but questioning their premise, their premises, or just asking why do you think that, do you, how do, is there evidence to back up that point of view?

And then responding to what they say, asking reasonable questions, poking at an idea in a reasonable, intelligent way. And then sometimes just agreeing to disagree. Yep. Again, your point is not to win and crush your opponent into submission. It’s to bat around the idea we’re hopefully at the end where you’re genuinely curious why the other person thinks the way that they do with the goal of maybe learning something from them.

Maybe it’ll change how you think a little bit, maybe you’ll change how they [00:27:00] think a little bit. But at the end of the day, Ideally, both parties have learned something, have enjoyed the back and forth and the process of trading ideas and questioning each other a little bit to pushing a little bit.

You know what, why do you think that, can you explain your reasoning? Yeah, that’s legit. That’s good. That’s not gotcha. That’s just asking a legitimate why question. So that’s how I go about it.

Casey Cheshire: Love that. I feel like if we could do more of that. To your point though, it has to be organic, right?

I think whenever you get, you add in those, I’m gonna disagree with you on purpose. Straw mans are interesting that doesn’t happen that often. I think you and I might tie that all back into a good prep call’s finding out, oh, I’m gonna disagree with you on this, and then you both know it.

And then you’re both ready.

Jeremy Shere: Yeah, exactly. When I’m [00:28:00] doing a prep call if, especially if we don’t already have a topic set, sometimes I’ll ask the guests, what’s something in the world of B2B content marketing that you disagree with, or that you have a contrary take on.

And sometimes they’ll be like, oh, yeah. We’ll deliberately choose a topic that, that there’s a debate about. And then that way we can get into that. And even if I might have a very similar point of view to the guest, again, you can play devil’s advocate a little bit and say I’ve, on LinkedIn there are plenty of people arguing something different.

They’re saying, actually it should be this way. What do you think about that? And that’s where I think you get the sparks start to fly a little bit and you’re getting into, and that’s part of what creates good content, I think. Are you creating

Casey Cheshire: these questions, all of them from scratch on a prep call?

[00:29:00] How much is scripted? How much is the same show to show? How much is different?

Jeremy Shere: You mean in terms of the prep call itself?

Casey Cheshire: Oh, just in, I guess even your show format. Do you have, use a lot of the same questions are almost Oh, I see all of them unscripted.

Jeremy Shere: Yeah. Good question. So I do not use the same questions.

I, I start basically fresh with each episode and I base it pretty much entirely on the prep call. And, the other research maybe that I’ve done there’s some overlap from topic to topic. Similar kinds of questions but the details, specifically what the questions are about are is unique.

Because each interview is unique, of course there are other ways to do this. Another form might be to ask the same set of questions to each person, which [00:30:00] can work very well. That way you can build up a body of episodes where you get all kinds of different takes or points of view, responding to the same set of questions.

And can be interesting for research purposes too. Good for content. Good for content. Yeah, it can, it definitely can be. I think that’s a totally legitimate way to go about it. I don’t do that. It just feels more natural to me to have a unique conversation each time that I’m trying to peg the questions to what the guest is most interested in and seems to be most passionate about.

Yeah. You’re

Casey Cheshire: listening for those little moments, either on the prep or even on the show for those little Oh that’s interesting. Now we’re gonna, we’re gonna go down that path. We gotta hear that.

Jeremy Shere: And and that’s another thing that hosts need to do, right? You need to be listening for, like I was saying before, for tangents and should we go there or not but you’re raising another good point.

You just have to be listening for [00:31:00] moments that, you know, through your experience as a host that like, ah, that’s really interesting. I’m gonna dig more into that, even if that wasn’t the next question on your list. Or you didn’t. It’s only coming up now and you didn’t think about it before, to be able to judge in real time, let’s pursue that point more because that’s a unique way of thinking about that thing, and to drill down on it.

Definitely think as

Casey Cheshire: I’ve gotten more experienced, I’ve used the standard questions less and less. Like on the marketing show, I have maybe four or five that I always ask as almost like a framework to the house. And then in between is, is me just winging it and having fun and doing follow-up questions and pr.

But for this show, I guess maybe it’s cause I’ve developed it from the last show, this show, it’s like that first question we started out and behind the scenes. Like I have a list up here of 20 questions that, yeah. Yeah. I think we reviewed a few of them together [00:32:00] on the prep, but you may not even get to if Sure.

These follow ups, I’ll just dance around.

Jeremy Shere: I and I think that’s another element to what makes for a good inter interview show is as the host not feeling like you have to get to every question. Yeah. And I think starting out, like when you’re less experienced you could, reasonably think that while I have 10 questions here and.

We need to get to them cuz that’s what this is about. And you just, it can cause a lot of anxiety and you can, and you might end up then with an episode where you get like very short clipped answers to the 10. And so yeah, you’ve covered those 10, but you didn’t really drill down on anything.

And it’s more of a surface level sort of survey type. Content than it is going deeper and really uncovering some new stuff. And I think you learn as a host, the more you go on that, if you [00:33:00] have a long list of questions we’re not gonna get to all of these in the time allotted, and that’s fine. Or you learn to just keep it to five questions or however many, you can reasonably get to in the allotted time and you just, even though there are many other questions you could ask, you learn to that could be for another episode. That’s okay.

Yeah. Great point. I’m gonna keep it, I try to keep things very, when I’m hosting a show to keep it very simple and minimal on my end. I want to try to and again, goes back to the prep call to try to hone in on what are the top three or four most important. Or interesting things that we want to hit and really try to hone in on those with the questions.

So I might only have three or four questions that I want to ask. Yeah, that

Casey Cheshire: Makes a lot of sense. And I think different people’s style. Some people love the planning. I. Some people love the adapting. Just [00:34:00] bring it. Just bring it. Yeah. And we need to be able to cater to guests from all walks of life.

The ones that, yeah. Nah, it’s fine. I don’t need to prep. I just wanna do you, on that note, do you allow people to skip your prep?

Jeremy Shere: That’s a really good question. It’s actually never come up, believe it or not really? I have not had a single guest who refused to do the prep call.

Casey Cheshire: Wait, I can introduce you to a couple that might be great guests on your show.

Okay. They will absolutely refuse. And I’d love to see the thread in the email of what do you think

Jeremy Shere: you would say to them? Yeah. So if that were to happen I think I would just roll with it and be like, okay. I would never force anyone to, to do a prep call. I think I would try to find an alternative, okay. Because, The, the only way that would be completely okay for me is if we have the topic locked in place. [00:35:00] And maybe I was able to do enough research to get the gist of what this, where this person is coming from, where the guest is coming from, maybe they’ve done other, they’ve talked about this on other podcasts or in other, formats.

So I’ll check that out and at least have some place to start from. Without talking to them about it. Or I might say okay, we don’t have to do a prep call, how about we just do this by email? Like I’ll send you a few just quick things and if you can just respond even just a few lines to orient me, I.

It’s hard. I don’t think I would be okay with just absolute blind, just show up and let’s just talk about some stuff and I’ll hit record because I feel like that’s gonna be a waste of my time most likely. And ultimately a waste of the guest time because the episode’s not gonna be very good. So I think I would most [00:36:00] likely gently push back a little bit and at the very least say, can we do a quick email exchange?

And if they even refuse that, I guess I would have to make a judgment call then and it might come down to case by case like, then we’re just not gonna do this. If you can’t spare, 15 minutes for a quick prep call or two minutes for a quick email exchange, then I’m not sure how interested you are really in doing this with me in creating this good content.

Casey Cheshire: Yeah. I feel like it te tends to happen with. Either more seasoned speakers, more famous people, or people who thi you said this really well, were. Who are famous and your eyes are famous in their eyes, right? Yeah. Who feel like they might be. I had a former boss of mine, people go check out LinkedIn, try to figure it out.

He’s like a thought leader and I wanted to have him on the marketing show and he said no to the prep call for me. I just [00:37:00] wanna catch up too. And yeah. Mean you’re that busy that you can’t do that. And so we actually said let’s do it another time. Then, I just, other people I’ve like for this show, I, it is at Meta, so I, okay, great.

Don’t show up with no prep and let’s just see what happens. And then, and we actually talked about it and Natasha Miller, she was actually fantastic. But we talked about how she like, flat out refused to do a prep. And we talked through it. But I feel like, just like with forms, There are bad prep calls and then there are the prep calls that you and I did and then you do with your guests.

And I think a lot of people have that in their mind. They’re the bad ones, which is why they’re like, I’m not gonna show up for your half hour hangout session.

Jeremy Shere: And look, fair enough, I when you reach out and ask someone to be a guest on your show, assuming that you’re not paying them right, they are doing you a favor.

They are giving you their time. They could just as easily refuse. And so you really want to make everything as efficient as possible and not waste their time. [00:38:00] And so I can understand why some people just might be like, I look I’ll give you my time for the show. I just don’t, I can’t, I can’t do the prep call, all that.

Yeah. I think maybe the only situation where I’d be a hundred percent okay with that is if the person was a genuine, like big deal celebrity. And the calculation would be like, okay, I’ll probably never have a chance to talk to this person again. They have such a big platform that’s gonna help the podcast, there’s real value in it for the show because they can help promote it and all that.

And Okay. If they just refuse a prep call I’ll roll with that because their presence on the show would be so valuable. Yeah. I think that’s the only situation where I could justify totally skipping that.

Casey Cheshire: Totally. Seth Gordon said no, but hat said yes. I would like, yeah, sure, man, show up.

Talk to me about your purple cow. [00:39:00] But it’s interesting, and this may be like Jedi level for you and I, and maybe no one will follow with us, but the idea of, doesn’t it change the power dynamic, like you said you’re doing, they’re doing you a favor, but aren’t you doing them a favor too?

And what I like about it is it’s a mutual favor. So when, yes, one of these things, tips that balance, now it’s just oh please come on my show. I wanna get your name. And then they’re never gonna promote your show, but at least you’ll have their name on your show and it just, and it gets transactional and weird.

Jeremy Shere: That is a good point. And I agree with you. It’s not just a one way thing. You don’t have to technically, you disagree with that’s right. I completely disagree with you. Every word you said. No I agree with you in that it’s, yes, they’re doing you a favor.

I I’m not sure I would phrase it that as the podcaster, you’re doing them a favor. Exactly. I think that you’re offering them. An [00:40:00] intriguing opportunity that there’s value in the offer that you’re making. Yeah.

Casey Cheshire: Better said. I totally agree. You know what I mean? Yeah. Said.

Jeremy Shere: Yeah. And they’re not and anyone who accepts that, they’re not accepting it.

Just oh, I’ll do you a favor I’ll throw you a bone. No they’re accepting it only because they’re. They’re like okay, actually, this seems like there’s something in it for me. Something of actual value. Everyone acts. Everyone is self-interested in that way, and that’s not a bad thing.

That’s just how, that’s just human nature. That’s just how people are. Yeah, but I think that’s what I. Can make podcasting such a valuable like business strategy, right? It’s, I had another guy shout out to Mark Evans if he happens to hear this episode. A guy guy I know from LinkedIn and I’ve had on the B2B content show, he had me on his show called Marketing Spark, and he had a great way of putting this, which is that podcasting is like digital catnip.

It’s very hard to resist the allure of oh, [00:41:00] you want to feature me on your podcast? Who doesn’t, who isn’t at least a little intrigued by that, to be featured in some media. That’s, it’s attractive. It’s it’s like a compliment, so it’s just a really good way to get a yes from someone and to get some time with them.

And to get to know them a little bit. It doesn’t always work. You said Seth Groden de declined, and so Sure. Not everyone’s gonna say yes, but a lot of people will, especially people who are not famous, yeah. And don’t often get the opportunity to share their thoughts, and speak their mind.

You’re gonna get a lot of yeses. And if you’re a b2b, And you can get yeses from people that you want to talk to, that your organization needs to get to know. And that’s a good thing. Yeah. That’s a very valuable thing. And but you mentioned power dynamic and that’s an interesting [00:42:00] idea and I think an important one that I’ve thought about quite a bit.

And I think there is a balance of power between the host and the guest of a podcast that shifts over time. So I think when you initially reach out to someone, especially to someone you don’t know, asking them to be a guest in your podcast, the power rests mostly with the guest because they can say yes or no, right?

In fact, they have the full power to either agree, sure, I’ll come on, or no, I will not come on your show. And that’s, that’s fine. Once they agree, if they do agree. Once they do that and they commit to giving you their time, the power immediately shifts to the host because they’re, the guest is essentially putting their themselves in your hands.

And they are trusting you to lead them down the path to so that you are properly [00:43:00] prepared to be a good guest, that when you show up, you are ready to talk and be interesting and engaging. And you’re trusting them to not make you look stupid. That’s everyone’s fear. Yeah. That’s that.

At the end of the day, you’re gonna edit and cut this in a way that’s not what they were expecting, and that can be damaging to their personal brand or, whatever you want to call it. They are trusting you. So now as the host, you have quite a bit of power and with power comes responsibility as Spider-Man, as we all know from the Spider-Man, movies or comic books.

And you have a responsibility to the guests to be professional and make them and have a real, a great conversation. Create good content with them. And to, if you’re gonna, if it, if you’re gonna challenge ’em like we were talking about before, to do it in a professional and respectful way, all that stuff.

So I think that, that’s how I [00:44:00] see it, the power dynamic. It really shifts. And it doesn’t matter who the guest is. The guest might be a quote unquote powerful person, like a, in their organization they might be a ceo. They might be a, a C-Suite person. And I’ve talked to plenty of these types of people and I’m just a.

Lowly podcast host, sure. But once they’ve agreed to do it, they’re in my hands. And they, and that’s the vibe, and they trust you. And so you have to be careful with that as the host, you can, you have to live up to it.

Casey Cheshire: Wasn’t question like but he dancing to you like, cuz I feel like once you’re recording it’s almost mutual, right?

It’s almost mutual. But I’m gonna ask some questions and if we finish a question, you’re gonna look at me and go, okay, what’s the next one? Yeah, you probably not gonna be like, here’s another question you haven’t asked me yet that I’m just gonna start answering. Some people might do that like you’ve mentioned earlier, but Right.

Typically it’s like I’m leading, but man, [00:45:00] are we just, I dunno if you’ve ever, have you done like dancing lessons where Yeah. They make you like just. I’m just gonna move and you’re moving with me and no one’s really forcing anyone to do anything. I’m just saying, let’s go this way now and we’re just going together,

Jeremy Shere: Absolutely right. And as someone who is not good at dancing I’m athletic enough and can play sports and that, but when it comes to dancing, I just can’t, I’m just super self-conscious, whereas my wife is a good dancer. And the point is that it’s yeah when two people who are good dancers are dancing are like, wow, they just flow together.

It’s it just seems so natural, but it’s actually choreographed. And I think. A podcast interview is a little bit the same way that you’re right, that once you hit record, I think the power dynamic kind of levels out. You’re both at the table, maybe the virtual table, like we’re doing right now, chat, and then it’s a meeting of equals, the guest has done their part, they’ve [00:46:00] consented to be on this show, they’ve showed up, they did the prep call.

You’ve done your part as the host that you’ve prepared and you’ve written your questions and maybe shared them and you’re ready to go. And then once you hit record, yeah, let the games begin. And if everyone’s done their job well, then it turns into a really good conversation and the time flies.

And a guest that might have been a bit nervous at the outset, and I’ve had plenty of those, and they often will just admit it, be like, I’m a little nervous, and I always tell them, that’s fine. Totally natural. Especially if you haven’t done a lot of these types of interviews. But I can guarantee you once I hit record and we just start talking, you’ll forget that we’re doing an interview.

You’ll forget there’s a mic in front of you. You’ll just talk because you’ll, we’ll just get caught up in what we’re talking about and that’s true pretty much every time. Yeah.

Casey Cheshire: Love that. Where can people reach out? I feel like I could talk to you all day. [00:47:00] We’ll probably have to schedule some more of these things so we can just spend an hour on power dynamic and all these other cool concepts.

Where can people, they wanna reach out on content, b2b, content, on podcasting, on all the things. Where do you want them to go?

Jeremy Shere: Yeah. A couple of places. I am on LinkedIn of course, where you Hey, LinkedIn.

Casey Cheshire: Tell me about this. What’s this website?

Jeremy Shere: Oh, it’s this new up and coming website. You should check it out.

I think it might catch on. Yeah. Jeremy Sheer on LinkedIn. Last name s h e r e. So you can find me there. I’m on it pretty much every day. You can email me. I’m That’s c o N And if you go to our website,, you can find contact information there as well.

Yeah, always open for a conversation. Always happy to meet new people, so reach out. Love it.

Casey Cheshire: Love it and apparently shout out to Mark Evans that you mentioned earlier. [00:48:00] We’re literally recording tomorrow on this show, so we’ll Oh, no way. And I’ll, so we’ll give him a shout out and we’ll tell him to listen to this episode and I’m sure on his tomorrow that we’ll, okay.

Jeremy Shere: Yeah, please tell Mark I say hello.

Casey Cheshire: I will. Small world. Really is right. Man. Jeremy, thank you so much for coming on here. I man, to be able to geek out with a fellow wizard like this for an hour on these concepts that are way above just hitting the button and hitting record and letting it ride like this has been so much fun.

So thank you for coming on here. Thank

Jeremy Shere: you. This was a lot of fun. And I wanna say publicly on the show that I think you are an excellent host, a great podcast host, because Thank you. We did the prep call and it was and beyond just that we had a substantive conversation and kind of prepared.

We just got to know each other a bit and it was enjoyable. Yeah, and that’s something it’s, I don’t know if, I don’t know if you could learn that either you’re good at a conversation and just being friendly and open with people or you’re not, and [00:49:00] you are really good at making the prep call and this experience, doing the interview, like fun and engaging.

And that’s, that’s so important. It’s really important for good content. So thank you.

Casey Cheshire: Oh man, I appreciate that, that is really great to hear. I just love doing it, so I’m glad that my skills have caught up to my passion and and I’m learning something from the people I talk to, so Very cool.

And, In a fun segue to those listening, if you learn something, and I freaking know you did, because I literally have two pages of notes over here, front and back. Then share this episode with someone else one person, nine people, 3000 people. That’s thought leadership, getting good information into other people’s hands.

And with that, man, thanks again, dude. I appreciate you. Thank you. All right, everyone. This has been a crazy episode of creating the Greatest Show. It will catch you all next time.


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