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AP 1079: How Do I Deal With Imposter Syndrome, and How Do I Better Serve My Audience?

AP 1079: How Do I Deal With Imposter Syndrome, and How Do I Better Serve My Audience?

By Pat Flynn on

Ben teaches leaders how to work with their teams better through his website, Thoughtful Leader, and the Thoughtful Leader Podcast. He has a lot of experience as both a manager and a consultant from which to draw on, but he still runs into those same feelings of imposter syndrome when it comes to building a business online. He also has some great in-depth questions about audience segmentation and how to improve engagement that I think you’ll find super relevant and enlightening.

As I say so many times on this show, when I consult with people it’s not so much that I come up with some new idea that they’ve never even thought of, it’s that I give them permission to do the things they already know they should be doing. With Ben, the main thing is taking audience research a step further and actually having conversations with your followers to find out more about how they want to be engaged, how often, and what other questions they have that you could help them with.

Ben’s done a lot of great work already to build his business. If you’re wondering what to do with your segmentation, or what to do next, this episode is a good place to start. We also talk about overcoming imposter syndrome and how to teach and learn at the same time. It’s a good one so don’t miss out!

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Pat Flynn: What’s up, everybody? Pat Flynn here and welcome to AskPat Episode 1079. What you’re about to listen to is a coaching call between myself and an entrepreneur just like you. I’m here to help serve these individuals. But by these individuals allowing us to share this on AskPat, hopefully, you can get some help too. And today we’re speaking with Ben from Thoughtful Leader. He has a podcast and a website. He’s been helping leaders become better leaders for the last four years. He has a decent email list. He has some products, but he needs to get to that next level. And there’s some stuff that’s happening strategically in his brand that will allow him to get there that we talk about, but there’s also some stuff that’s happening in his brain that I guarantee most of the listeners, you listening, are also or have experienced in the past as well.

So we’re going to get into that in just a moment. But really quick, it is August 1st the moment this episode pops up and goes live. And that’s really exciting because August is a huge month for me. August 2019. If you are listening to this and you haven’t yet gotten your copy of Superfans, just get it now because this book is about to blow your minds and help you grow your business. Superfans is a book that’s going to help you better understand how to not just get people into your business but help those people who are in your brand, whether they are subscribers, followers, or customers, or fans, help them convert into superfans. Those people who will just consume everything you come out with. They’re going to just buy every single product. They’re going to share you and market for you without you even asking.

These are the most important people that you can have in your business who will help support you and future-proof your brand. As technology changes, as algorithms get in the way, it doesn’t matter. These superfans are going to be there for you. And if you pre-order your book before the launch date on August 13th and you submit your receipt at, I’m going to give you the audiobook for free. That’s right. The audiobook for Superfans you can get for free if you pre-order the book today at You can submit your receipt there and I’d love to give it to you. So thank you for letting me share that. Just I’m so stoked to get it in your hands, but I’m also stoked to chat with Ben today. So let’s not wait any longer. Here is Ben from Thoughtful Leader. Here we go. Hey, Ben. Welcome to AskPat 2.0. Thanks so much for joining us today.

Ben Brearley: Hey, Pat. How are you? Thanks for taking the time to talk to me.

Pat: Yeah. Absolutely. We were just talking right before I hit record about how there’s hundreds of people who have submitted applications and we’re picking them every day, but there’s a big queue. And I’m glad that you got in. So why don’t you really quick tell us about you who are and what you do.

Ben: I live in Perth, Western Australia, and the main thing I’m doing at the moment is running a leadership website called Thoughtful Leader, and that’s pretty much the thing I do on the side outside of my day job. At the moment I’m in sort of a middle management role, and I’ve had a lot of leadership roles over the last ten to fifteen years. And about probably five years ago, just as some context, I started getting a bit disenchanted with the state of leadership that I see out in some of our businesses, and I started deciding to write about it and sort of share my thoughts with the world. Obviously, talk about my experience and what I think leadership should be like. So that’s what led to Thoughtful Leader, and it’s been a bit of an evolution. So it’s been a good four years putting the site together and trial and error over and over again to try to work out what I’m talking about and what my audience should be focusing on and that sort of thing. So yeah, that’s basically what I’ve been up to.

Pat: That’s really cool, Ben. Any particular type of leader that you are focusing on or who’s the typical avatar for your audience?

Ben: So for my audience, it’s generally corporate sort of leadership positions. Generally in the middle management team leader type position. I’m not really focusing on executive leaders or anything like that at this point because I’m not one of those myself, and therefore I don’t want to pretend that I have those skills yet. That’s generally who it is. I did do a survey of my audience actually recently, which was a bit of an eye-opener because I assumed that a lot of people would be finding my site because they’re new leaders and they want to learn about leadership. But what I actually found was most of my audience are really quite experienced leaders who have leadership problems. That’s not people who want to learn how to sort of start leading, which I thought was quite interesting.

Pat: Great job. Well, surveys can definitely be eye-opening in that way. What’s the URL for the website one more time?

Ben: So it’s, all one word.

Pat:, and may I ask you what your definition of a thoughtful leader actually is?

Ben: So for me, my definition of a thoughtful leader is one that is intentional about making decisions and intentional about the way they lead people. So it doesn’t mean you’re the nice girl or guy all the time. But it does mean that you think deeply and introspectively about the impact you have on your team and the people around you when you’re making decisions and when you’re leading people. And so that’s really the crux of it for me.

Pat: I love that word, intentional. That’s so important, and I a hundred percent agree with you. Okay. So it sounds like you’ve been doing this for a while, four years. So what’s on your mind?

Ben: I’ve had various things happening. So I’ve been creating different products and that sort of stuff with varying levels of success. And obviously, the big advice now is to test your ideas before you create products. So I’ve obviously learnt the hard way by not doing that. But at the moment I’ve got a bunch of eBooks and things that I sell on the site, and I’m starting to pick up a few sales here and there. It sort of trickles in. So I’ve got an email list, which is built to about twelve hundred people. I just started a podcast a couple of months ago. I really just used that as a solo show to provide a different method for my audience to consume the content rather than have guests on or anything like that at the moment.

Pat: Are you sort of rereading your blog posts there or are they different topics?

Ben: What I’m doing is actually recycling older content that a lot of people might not have seen yet.

Pat: Very cool.

Ben: So I sort of every week I share out the new blog posts, and then a podcast, which is a new episode but it might cover some old content that someone hasn’t come across yet. So I sort of give people options.

Pat: Very nice. And it’s the same name, Thoughtful Leader.

Ben: Yeah. It’s called the Thoughtful Leader Podcast. It’s on all popular podcasting platforms as far as I can tell.

Pat: Perfect. I’ll check it out. I’ll put it in the show notes for everybody. But continue on.

Ben: Yeah. So my issue I think . . . So I’ve done a bit of segmentation and that sort of stuff. What I need a bit of guidance on is really how I’m cutting up my audience, and how to serve them better with my content. And I think what I have a bit of is an engagement issue with my audience as well. What I mean by that is I do get feedback and good feedback on my content and that sort of stuff. But I think I’m trying to gauge the level of engagement I should have from my audience and whether I’m just not producing the content in the right way or whether my audience has certain characteristics that make them difficult to engage or able to engage them in a different way.

So as an example, a lot of my email list, obviously it’s been built up over the last three years or so. So some of these email subscribers may be quite old now, couple of years old. But you send out emails and things like that. Often I don’t get too much of a response if I’m trying to do surveys or anything like that. So asking for feedback and stuff like that can be a bit difficult. But I also wonder because if my audience—and basically they’re mostly leaders and a lot of them sign up with their work addresses and stuff like that. I wonder whether I should be engaging them in a different way.

Pat: Have you asked how people prefer to engage in your survey?

Ben: I haven’t actually. That sounds like an obvious one.

Pat: Well, it sounds obvious after the fact. We never know the right questions to ask until we run these surveys, but it might be interesting to . . . I don’t know if you have some people who may be superfans or high engaged people in your audience already who you could reach out to, even can get on a phone conversation with or a Skype conversation. That’s actually been one of the best things that I’ve done in my businesses. And even now that email list is two hundred and twenty thousand people, I still take the time every month to speak to or try to talk to, in person—whether it’s online or offline—some of my new email subscribers so I can ask them questions. I know that they are recently subscribed so that I can sort of reach out to them and they’re going to be excited about the opportunity to kind of offer feedback right away versus some of the older email subscribers. They might have different email addresses or different modes of communication. So have you ever actually had a chat or sat down or talked to some of your audience members before?

Ben: No. Not in person. It’s always over email. So I get questions and things like that, and I’ll chat over email. But not actually in a personal conversation.

Pat: Okay. Well, that’s like a good first step, right? Because email is—for the people who use email and communicate via email—it’s a great way to get to know somebody and kind of have it on your time or their time whenever it’s convenient. But one of the coolest things you can do and I would challenge you is to maybe, by the end of the month, try to have a conversation with two or three people in your audience. And maybe even send an email out and say, “Hey, I’m doing a free call, and I’d love to just get to know you and what I can do to better serve you as a leader in your space. I’m not going to sell you anything. I just want to get to know you.”

And what I’ll do is I’ll just randomly reach out to ten brand new email subscribers each month, randomly, and it’s funny because some people just don’t believe that I want to get on the phone with them. But honestly, it’s one of the best things that I’ve ever done because those conversations . . . First of all, some of those conversations are really short, and kind of just nothing really comes out of that. But other conversations, I mean, I’ll talk for hours sometimes, and I’m asking questions like, “Well, what are you struggling with right now? What have you tried to do to start your entrepreneurial endeavors, and what has been stopping you?” And then I’ll even share some new ideas of things that I’m thinking about creating. “Hey, I’m thinking about creating an email marketing course. Is that something you would even be interested in? What’s your gut reaction to that?” And then this is a good opportunity to go, “Hey, if I wanted to follow up with you later online, what would be the best way to communicate with you? Would you prefer email? Where are you and what’s easiest for you?” And then you get to hear, in their own words, not just the problems that they’re having and their ideas and what’s working, what’s not, but very specific answers to questions like that.

Ben: Yeah. Okay. No, that’s good advice. And I think it’s something I sort of . . . Yeah, I think I have a bit of imposter syndrome going on, and I’ve been battling this for quite a few years.

Pat: Oh, interesting. Okay.

Ben: So it’s interesting because at work, I’m quite confident in my leadership role and that sort of stuff. And then when it comes to this sort of stuff with online business, you’re putting yourself out there, right? So it’s taking me a while to get comfortable with that. And I think that sort of stops me from . . . I’ve actually got a lot better, but really putting myself out there is something I’ve struggled with I think.

Pat: It’s definitely not an uncommon problem I’ll tell you, Ben. I think everybody who is listening to this can relate. I definitely can relate. I even have moments during the week when I am just wondering, “Well, why am I doing this? Who I am to talk about this? Am I even qualified?” You even hinted at it a little bit in the intro when you were saying, “Hey, I’m not going to talk about executive leadership because I’m not there yet. I don’t feel qualified to talk about that.” And so I can hear hints of it. Why do you think that is? Where is that coming from do you think?

Ben: It’s interesting. Interesting question. I think it’s . . . I mean, in Australia we have a saying, I don’t know if they say the same thing in the U.S., but like tall poppy syndrome. Do you have that?

Pat: Bit head syndrome kind of?

Ben: Yeah. It’s the same sort of analogy you used, I think one of your recent—might be SPI podcast, episodes where you’ve got the bucket of crabs, and one of them tries to crawl out and they claw him back in.

Pat: Yeah. Yeah.

Ben: It’s similar to that. So the poppy, if a poppy grows too high, that’ll be the one that gets chopped off. So everyone tries to keep low and not put their head above.

Pat: Actually that’s really interesting you mention that because when I was last in Australia, I went to visit my good friend Darren Rowse from ProBlogger who’s on the East Coast of Australia. You’re on the West Coast, right? In Perth.

Ben: Yeah. That’s right.

Pat: Have you been to a ProBlogger event before?

Ben: I haven’t. No.

Pat: They’re really good, and I think he does do them in Perth every once in a while. But anyway, this conversation of Australian culture came up because I do these income reports where I share how much money I’m making, where it’s all coming from. And somebody, I can’t remember who, but we got in a conversation just the fact that Australians would never do that. And it’s kind of like . . . It’s almost like an interesting culture, and correct me if I’m wrong, where you kind of want to stay average so that you don’t get too much spotlight on you. Is that sort of the . . . Or maybe that’s the East Coast thing. I’m not sure.

Ben: No. No, no. I think that translates across. I used to live on the East Coast for a couple of years as well. So yeah, it’s very similar across Australia, but I think, yeah. I think that’s a big part of it. Culturally, I mean, we have celebrities and things over here, but if they’re not modest and all that sort of stuff and if they’re bragging a lot and things like that, they tend to get shot down.

Pat: Oh, I think I remember what it was. It was around the time of the Olympics, and somebody from Australia won second place. They won a silver medal and they were crying because they didn’t get gold. And everybody was saying, “How could she do that? She should be thankful she got second. She should worry about getting gold.” It was this big debate, and people in the U.S. were like, “No. That’s completely . . . We get that because we want to be first and the best all the time.” It just brought up this really interesting conversation about culture. But anyway, I don’t want to get too off tangent here. But it’s just a really interesting conversation about culture, but that sort of syndrome, imposter syndrome is not just in Australia, it’s everywhere. And for me a lot of it comes from, “Well, I don’t know if what I’m putting out there is good enough. There’s a lot of other people who could do it better.”

Personally, I’ve realized over time that although I’m sharing a lot of the same stuff that other people are sharing, I share it in my own way, and people want it from me. People respond to the way that I am, and that’s your tribe. Your vibe attracts your tribe, and I’m sure you’re building an amazing and very strong tribe of leaders on your end as well. Speaking to what you were saying earlier about the executive stuff, I do want to cover that really quick because I don’t want people to assume that if you don’t . . . I understand where you’re coming from when you say, “Well, I’m not an executive so I don’t have that knowledge.” But you can still be somebody who learns how executives lead and teach along the way.

Ben: Oh, of course. Yeah. When I say that, I don’t mean I have that experience because I’ve done quite a lot of . . . Previously in my career, I did quite a few years of consulting work for some pretty large international consultancies. And during that period, I dealt with executives and stuff all the time. So I am used to dealing with senior leadership like that, but I guess I’m not really writing about that. I’m more writing about the direct people management/people leadership type stuff.

Pat: Cool, and that’s okay. That’s totally okay. Okay. So from here, I want to continue to dig deeper into some of the next steps for you to help you. I think getting into these conversations, even if you just position it as a ten to fifteen minute call with somebody because you want to learn more about how you can help them. Always position it for their benefit and have those conversations and just really be curious about what you can do and how these people prefer to communicate. And I think you’re going to learn a lot, and in addition to that probably hear some really amazing feedback. At the same time, that might encourage you and help you battle this syndrome.

Ben: Yeah. For sure. I think it is something that’s been holding me back, but over the years what’s happened is I’ve gradually got more and more frustrated where I’ve gone, “Oh, you know what? Screw it. I’m just going to put this stuff out there.” And slowly I’ve been breaking down these barriers. But I haven’t really had that personal contact with my audience too much. So yeah, that’s something that would be really beneficial I think.

Pat: So that’s one method. The other thing that you could do on the same lines, and this is something I talk in my book Superfans. It’s where you are providing value. People know who you are. They’re active members of your subscribership, but they’re not yet members of a community. And this is sort of bringing people to a place where they feel like they belong. So there’s some really cool things that you can do like small things like giving your tribe a name, right? Where people can go, “Oh yeah. I’m one of those.” Just like people who follow me, they’re known as Team Flynn. People who follow John Lee Dumas, they’re known as Fire Nation. If you follow Star Trek, you’re a Trekkie, right? And then they start to sort of come together for that sort of commonality under you that you’ve created. So that’s one small thing that you can do.

Another thing you can do is you can start featuring members of your tribe on your podcast, on your blog, and that brings some really good community elements together because then people will start to respond. Because it’s not just you, it’s somebody just like them who is maybe just a few steps ahead that is getting featured, that is getting noticed. And that’s going to encourage other people to engage more because it’s sort of a community aspect and feeling to that. And then there’s the bigger things you can do like meetups, even big events, virtual events, perhaps, is a good thing where you are actually bringing your most engaged people together in one spot, and then using that opportunity to engage with them. Like whether it’s online in a virtual summit situation or even something like a webinar or live stream or a more official event like people flying in or coming to town for a coffee meetup or a multi-day event. Any of those things resonate with you?

Ben: Yeah. I think most of it would have to be online. The majority of my audience is actually in the U.S. Actually sort of where I’m targeting, I don’t want to get into this thing where I’m a local. I want to be able to do international and also run mainly online, and get more passive income rather than do consulting in person and stuff like that, trading time for dollars basically. The community name thing I think is a good one. The meetups and events, I think I’m not quite ready for that yet, and I think it’s a challenge with the local versus online. Perth is quite a remote city, actually, in terms of it’s been called one of the most remote capital cities in the world or something. It just takes quite a while to actually get here.

Pat: Sure, okay.

Ben: But it’s a nice place, don’t worry.

Pat: Another type of event that you could do that really gets people to move and communicate is something like a challenge where there’s a specific date and a specific time period by which people are taking some sort of action. That’s kind of cool because it really can start to mobilize a stagnant audience sometimes when there’s a purpose behind a certain time period. And this has proven to be very successful across all kinds of different brands, and it could take some time to just come up with a creative forty-eight-hour or seven-day or five-day, you know, week challenge to do something as a leader, and then have people kind of report back. And offer like a prize to somebody at random who engages in some of the sort of reporting and things like that.

Ben: Yeah. That’s an interesting idea. I do wonder whether this could just be my imposter syndrome talking. But the leadership audience I’ve got . . . So I wonder whether I haven’t niched far enough because, I mean, leadership is pretty huge, right? There’s so much stuff on the internet around. You can search all sorts of leadership stuff. You got your Michael Hyatt’s and your Brian Tracy’s and all these guys, which is fine. I’m not trying to say that I can’t compete with that because you can in your own way. But I think what . . . So what I did was start off quite general a couple of years ago because I thought, “Yup, okay. Cool. Everyone will write about leadership.” So I started on that, and it was quite general. Now I start to think, “Well, okay. I’ve looked at some of the other leadership sites out there.”

I looked at your SPI site as well, and I notice you’ve got the categories of things like affiliate marketing, podcasting, and that sort of stuff to actually help segment that audience. So I’ve tried to do that as well, and I’ve sort of chosen things that I’m quite passionate about. And I’ve had some feedback from surveys and things that people have the same problems, and tried to segment them that way. Because I wonder, and these are things like time management, motivating team members, and also building confidence in leadership as well. So I do wonder whether some of the engagement or the limited engagement that I’m getting is because I’m not hitting the right people in the niche, and they’re sort of signing up for general leadership stuff rather than I’m hitting an actual need that they have. Do you understand what I’m getting at?

Pat: I completely understand, and I think that what I’m seeing is maybe there’s just a missing piece in the middle to connect these people who are coming in for more general sort of sense of leadership and helping them understand what their most important and top priority is in the space of leadership. To then dive into that area of content on your site. I’m very, very encouraged about the fact that you are segmenting by topic, and I think it’s totally okay to do that. And what’s really interesting, and you might see this on my side, especially on some of my other channels like on podcasting and especially YouTube, you’re going to start to see this more. So it’s totally cool to have different categories, but you’re going to find some categories are going to be more lively and more engaged and just more interesting to your audience and others.

That doesn’t mean that you necessarily . . . In some cases, it might mean just like, “Woah, ninety percent of my stuff about this is just getting so much engagement. I’m just going to completely change my brand.” And that happens sometimes. But if you know that leaders require all of these different aspects, which I think they do, then it might just mean that a majority or more of your content is about that particular . . . Maybe it’s more about time management versus the others. It doesn’t mean you don’t talk about the others. It just means you talk about the ones that are most popular more. Are you seeing any one of those particular topics sort of being responded or trafficked more?

Ben: Yeah. I think the motivation, team motivation is one, and I’m pretty strong on . . . A lot of my content is about—when it comes to motivation, it’s not about short-term rewards and things like that. It’s more about sustainable motivation within teams so that people enjoy coming to work and that sort of thing. And I think that is the stuff that I’m seeing gets a bit more traction and about sort of employee engagement, that sort of stuff.

Pat: I like that. So that’s where I would start to build out a couple things. Number one, have a clear way for people who come across the website to understand that that’s sort of like a top priority that you talk about. Whether it’s in the tagline or in the navigation menu, you got to hone in on that so that people can go and find themselves there. And of course in your general content or other content, it can make its way into that content too, and you can cross-link and get people onto an email list, which would then be the next step. So however people get on email, you want to start to segment your audience so you can understand, “Okay. Well, here are the group of people in the twelve hundred who have basically told me and said and self-segmented into the team motivational segment,” or bucket, if you call it that. This is definitely playing on a book called Ask, which is really helpful to me. [Full Disclaimer: As an affiliate, I receive compensation if you purchase through this link.]

Ben: I have read that.

Pat: You have read that. Great.

Ben: Well yeah. I sort, and I did start the four of those steps. And when I did the survey stuff, I did actually . . . I found it a struggle because my audience was responding with things I found very difficult to put into different buckets. Like it wasn’t obvious what the categories were from that method I was trying . . . my responses anyway.

Pat: Yeah. It can be tough. I remember we collected five thousand responses for open-ended questions. This is like definitely a chore to go through, but, I mean, I could’ve created forty-five different segments based on what people said. But I had to really make a decision on what the top things were, and you have made that decision already it seems like, which is good because a lot of that probably comes from your experience just answering questions and helping people.

Ben: Yeah. Exactly. I guess the concern I have is that these things are time management, building self-confidence, and then understanding how to motivate team members. Then I have a general bucket where I’ve written a lot of content in the past that just doesn’t fall into those categories. But I generally try to stick to the top three ones now. But my concern I guess is that that doesn’t cover everything about leadership, right? For example, if someone wanted to specifically know about people management or something like that, they might think, “Well, they don’t have that stuff on this site.” So I guess is that . . . Do you just live with that?

Pat: Well, the thing is if these are your target categories but people are still asking questions, you should cover them in some way, and it can go into a general category. But where I was going with my sort of YouTube example is that my podcasting stuff has definitely picked up over the last year. So I’m leaning into that a little bit more, and it doesn’t mean I don’t have content about setting up your LLC still. I’m still publishing that stuff because that’s still helpful for podcasters, too, who are creating their own businesses. But you’re going to see like thirty percent of my content on the blog be about podcasting in the future and actually even more on the YouTube channel about podcasting. Those are the signals that people are giving me but also Google and YouTube are giving me with analytics, too. So I would definitely dive into analytics, too, in addition to the conversations that you’re having with people to understand, “Okay. Well, where should my sort of top focuses be? Where should I spend the next sort of three months creating content and building out these funnels?” Because once you get your most popular one, which is motivation and team management, well then you should also have within that a series of emails for people who have self-segmented into that space. This is where it starts to get overwhelming, Ben, because it’s like, “Oh my gosh. I have these four categories. Now I need to build funnels for each of them. Uh, my head’s going to explode.” Start with one, right?

Ben: Well, to be honest, I’ve got . . . The reason I switched to ConvertKit from MailChimp [Full Disclaimer: I am a compensated advisor and affiliate for ConvertKit.]

Pat: Good for you.

Ben: It’s a lot easier. So I finally committed to paying for something because I was holding off on that for a while. Yeah. So I’ve got a bunch of sequences already set up. They’re just quite basic. So they’re not really . . . They’re not these fifteen-email-long sequences because at the moment I don’t have any large products to sell. I only sell sort of small eBooks and things like that. So I don’t really have any sequences leading to a large core sale or anything like that at the moment. So yeah, they’re real basic. So they’re only three or four emails maximum, but I do have them for each segment at the moment.

Pat: Oh, good. Good. Okay. So then definitely go into the analytics for both Google and even your email. ConvertKit has some good reporting features to just . . . This is where you start to kind of fine-tune, right? I think you’re ahead of the game, actually, with where I know a lot of other people are at. So I would just encourage you to keep fine-tuning and stick within these categories, primarily, but continue to listen to your audience. And main thing, going back to what we talked about earlier, is to see if you can just have conversations with them. I think that your mind’s going to be pretty blown with not just the interactions that you have and the confirmation that you are doing a lot of great things but a lot of the help that they’re going to ask for and some of the more clear answers to some of these sort of unknowns.

And then the final thing I want to talk about is just like it’s interesting because back in the day when I started blogging, the blog was where everybody was communicating, right? It was always the blog, and email lists were the two things. Email and the blog. Now blog comments are at all-time low and email is getting . . . People’s attentions are everywhere. Email, social media, and YouTube, podcasting. It’s tough to get in front of an audience, but the best thing that you could do is sort of do a little research if you haven’t done so already with where else does my audience exist? And there’s a few things you can do for that. Number one, you have this podcast of yours. If you go into iTunes, which later will turn into Apple Podcasts on your desktop, it’ll show you people who listen to your show also listen to this show or another show. And literally, your audience is listening to them too. So you can connect with those other podcasters and maybe even do a guest swap or something to share those audiences together and get in front of more people that way. Facebook groups, there might be other personalities who have your audience too who could benefit from your particular stance, and you can kind of work together in that way.

Ben: Yeah. No, that’s good. Thank you for that. I just have one more question actually.

Pat: Yeah, sure.

Ben: Yeah. On that segmentation stuff. So the thing I thought originally was, “Okay. If I’ve got these three main segments, do I have to start producing content for every segment every week, right?” And I was thinking that’s going to be overwhelming. But do you just basically produce content and send it to all your list anyway? Do you still do that even if their particular interest might not be that particular post for that day?

Pat: I would be more selective instead of sort of blasting everyone to everyone. First of all, you don’t have to write for every category every single week. That’s definitely overwhelming. I would stick to your primary schedule, and just focus more heavily and lean into and write more about the things that are the most popular and answer those questions. So I think number one, and there’s some really interesting things that you can do with ConvertKit. For example, you can have people sort of click to tag themselves to say, “Hey, do I want to be notified every time an article about . . . ” So you could do this a couple ways. You can go directly and say, “Hey, if you want to know every time there’s a team management article that comes out, if you want to be notified, click here.” And you can tag them in ConvertKit as like “high interest—team management” or whatever the category you called it in ConvertKit.

Or you could go the other way around. You can send an email to everybody who has subscribed to want to get every single email. So I have something that goes out every Friday called “The Digest,” which has sort of a list of all the content from all the different platforms so that it’s not overwhelming. Because if I literally sent it to everybody every time I publish something new, it’d be like twenty emails a week. That’s not good. But what you could do is say, “Hey, click here, and I will make sure that you never miss anything because all of this is helpful.” So you could have people self-segment and basically give you permission to send them an email every time you come out with anything. So you can kind of doctor it up in any which way you want, but there are really interesting things you can do with Convert Kit to allow people to even get some preferential when it comes to how they want to receive content. Which by the way, I’m sure you seen this a little bit, but when you start to get into the segmentations in your email, you’re going to start to get higher open rates. And you’re going to get people to respond a little bit more than if it was just one general bucket alone. So use the conversations that you’re going to have and let them know that, “Hey, how would you prefer to receive emails from me? Do you want them all? Do you want just the one about the thing?” And you’ll hear directly from the audience that you’re building for what to do.

Ben: Yeah. I do think that, for example, I like to write about time management and that sort of thing, but I think yeah, I get a few unsubscribes from that, not heaps, but a couple. When I think if I harp on that too many weeks in a row, people start to go, “Oh yeah. Is this just about time management now?” So yeah, that can be avoided. Yeah, that’s good.

Pat: And on unsubscribes, I mean, people are going to unsubscribe. And that’s okay. Like I look at it as making your list stronger, right?

Ben: Yeah. I’m not too worried about that. But I am aware that, yeah, I think you’re right. I don’t want to start bombarding everyone with every piece of content unless they want it.

Pat: Exactly. There you go.

Pat: Cool, man. We covered a lot of stuff. What’s the general consensus and thought about the conversation and sort of what have you learned from this?

Ben: No, it was really good. I think you just sort of said things that I knew I had to start doing. It’s one of those things where you say you’re giving us permission to do things, right?

Pat: Yeah, dude. It’s so common here on AskPat. It’s hilarious.

Ben: Even when I got the invite for the podcast a couple of weeks ago, I started to think, “What are these things that Pat’s going to be telling me I should be doing?” But anyway, well number one actually is the calling and organizing some calls with some of my subscribers. I think that’s just a big one for me to start breaking the back of some of this imposter syndrome stuff a bit better. Even if the results that I got back were not great, it would still be a massive step forward for me to do that I think. And that will just I think unlock a lot of other things that I could do and be a bit more out there with what I’m trying to do. So that’s a huge one, and I’m going to force myself to do that.

Pat: Yeah. It’s almost like, and I would imagine that when you teach leadership and especially for management positions, it would be unheard of for you to say, “Don’t talk to your team.”

Ben: Yeah. Yeah.

Pat: Right? So basically what you’re doing is you’re talking to your team here.

Ben: Well, I have a bunch of stuff about building leadership confidence and stuff, and one of them is putting yourself out of your comfort zone. And I do do that at work, but I have struggled doing it with my online stuff. So I can, yeah. I need to do that. That is a big step I need to take. The other thing, it’s just around the segmentation. I want to get smarter with the email segmentation. So at the moment, because I transitioned from MailChimp, I’ve sort of got a lot of people in one big bucket. So I’d like to send them out a sort of segmentation email so I can get them to self-select a bit better, and then start sending the content to the people who want it specifically. I know you’re right. That will be a lot better for engagement because people are hearing, reading the stuff they really ask for rather than anything. I think that’s huge.

Pat: Ben, this is great. I can’t wait to reconnect with you in the future just to kind of see how things progress. One more time, can you let everybody know where to learn more from you.

Ben: Yeah. To learn more from me, you can go That’s the main place, and that’s got links to my podcast and things, which is called the Thoughtful Leader Podcast as well. Yeah, I’m also on LinkedIn obviously. So you can connect through that. But that’s all through the website as well.

Pat: Awesome. Thanks, Ben. I appreciate it. Well done, and we’ll talk soon.

Ben: Yeah. Thank you for that. I will get to work on this stuff.

Pat: Awesome.

Ben: Thanks, Pat.

Pat: Alright. I hope you enjoyed that episode with Ben. Again, one more time, you can find him at Thoughtful Leader. Just go to or you can look up the Thoughtful Leader Podcast on your app right now. And, again, Ben, just thank you for coming on. And for anybody else who wants to get coached just like Ben today, all you have to do is submit your application at There’s a little button in the middle of the page that you can submit your application, and I’ll reach out to you if it’s time to get you on the show. We’ll go through this process just like we did with Ben.

Thank you all so much for your support. I appreciate it. I appreciate all the new reviews that have been popping up on iTunes and Spotify and Stitcher and everywhere else. And lastly, I’m just very thankful to everybody who has helped support me with my new book, Superfans. If you pre-order it on Amazon or Target or even Barnes and Noble today, just submit your receipt at, and you’ll get the audiobook for free on launch day. So thank you so much. I appreciate you. Team Flynn, you’re amazing. I’ll see you in the next episode. Team Flynn for the win.

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