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Speaking, Presentation, and Thought Leadership | Thom Singer

Getting Connected and Staying Connected in a Diverse Thought Leadership World.

An interview with Thom Singer about thought leadership strategy in speaking and presentations, and how to measure thought leadership success against audience interest.  

We interviewed Thom Singer, the “Conference Catalyst,” host of the podcast, Cool Things Entrepreneurs Do. He’s got decades of thought leadership speaking, presenting, and marketing experience, and he’s here to teach us a few things about thought leadership strategy, and how to be the best presenter your clients have ever seen!

Thom shares his journey from sales and marketing to Thought Leader and how he realized he wanted to be a keynote speaker.  Thom details how he gets bookings and the various touch points he uses to stay on the radar of potential meeting planners.  Peter and Thom discuss the sometimes difficult task of making both audiences and the planner who hired you happy.

Four Key Takeaways from the Interview:

  • Thinking of your thought leadership content through many different modalities.
  • Creating touchpoints to check in after a thought leadership speaking engagement, and converting your audience into clients.
  • The “two masters” a good thought leadership speaker should keep in mind.
  • Why thought leaders doing speaking engagements should involve themselves in the conference beyond their stage time.

If you enjoyed this podcast on thought leadership speaking, check out Thought Leadership Leverage’s home page!



Peter Welcome, welcome, welcome. This is Peter Winick, I’m the founder and CEO of Thought Leadership Leverage, and you’re joining us on the podcast today, which is Leveraging Thought Leadership. Today my guest is Thom Singer. Thom is an advisor to executives, a speaker and content creator in a successful career in sales and marketing, and then became a growth leadership speaker back in 2009. A decade later, he has brought his energy presentations, an action-oriented content to over eight hundred audiences. Thom knows that as a speaker or master of ceremonies, he has a responsibility to set the tone for a strong conference experience. He’s also the author of twelve books. I’m not going to name them all because we’ll run out of time. And he’s been interviewed over 400 entrepreneurs, solo entrepreneurs, et cetera, on his podcast, which is Cool Things Entrepreneurs Do. So without further ado, here we are. How are you, Tom?

Thom Singer Peter, I’m doing great. Thanks for having me on your show.

Peter So let’s. Oh, my pleasure. Let’s start with the transition, because I think there are a lot of people that aspire to hope to wish to dream about actually doing it. Right. So maybe go back if you’ve been doing this since 2009. So let’s go back like ’07, ’08. What was going on in your head and then what gave you the confidence to finally say, I’m there?

Thom Singer Well, I spent my career in sales and marketing. And when you’re in sales and marketing, you go to a lot of conferences, either one your company puts on to bring into the sales team or things you go to for clients. And I would sit in the audience and watch the speakers and think, wow, she or he they have a better job than I do.

Peter Like they work less. They’re only there for an hour. Right.

Thom Singer Well, I had no idea even what they got paid, but I thought what a cool way to live, to be able to go and talk to people. So I would go up afterwards. I buy their book. I’d stand in line and I’d ask them about what they did and how they did it. And there were a lot of people who had sort of what I now call a traditional speaker model business. And I was like, that seems like I would be so happy if I could do that. And some of them would be like, well, let’s go have a cup of coffee and I’ll tell you everything you could ever need to know. Others were kind of jerks like, you know, oh, well, you’d have to be like me. And I just was quick at weeding through the wheat and the shaft of those boot. And I got a lot of guidance. And I started doing it on the side. I wrote a book. I was, you know, speaking to Rotary Clubs and companies. And then on April 1st, 2009, which arguably the bottom of the Great Recession.

Peter And April Fool’s Day!

Thom Singer And yeah, the irony of being laid off on April Fool’s Day is never, never lost on me. I was laid off and I decided I’m just gonna go for it. I’m going to follow this dream and see if I can make it happen.

Peter And so let’s recap. So step one is get fired.

Thom Singer Yeah, well, that’s not even that’s not even funny in our current situation because.

Peter Yeah, right. Right. Yeah. OK. So you were. So if that didn’t happen, this was already on your radar, on your mind. Did you have goals set up, did you say. Once I hit this or was in retrospect was actually a good thing, that it was the kick in the butt that forced you to say, OK, I guess now is the time.

Thom Singer So, Peter, I think it’s both. I actually the company I was working for, actually my boss was fantastic. She was amazing. She knew I wanted to do this when she hired me. And she said, how long do you think your runway is until you can build up your reputation to be able to do it? And I told her I thought it would be about three years. And so she said, I’ll make you a deal. I’ll hire you. I’ll give you extra vacation days. She paid me a little less, but I was free to travel, to go give speeches because I perfect. I had some flexibility and it was about a little less than two years later when the recession just got too much. And she had to lay off half her company now. To her credit, she saved the company. It’s bigger and stronger now than it ever was. But I was part of that cut of 50 percent because you don’t need a high paid director of marketing when there is no one to buy your product.

Peter Yeah. Yeah, yeah.

Thom Singer Oh, yeah. It was a combination of I was doing it. I had goals, I had plans, but I often wonder would I have done it a year later without the kick in the pants?

Peter Sure.

Thom Singer It worked out well.

Peter So let’s pivot for a bit. I want to. Parking well not parking lot. Let’s not talk about this sort of the requisite skills that are required. Because that’s table stakes and I don’t want to underplay that because most people don’t have that. You clearly have the chops of what does it take to be a great speaker. I want to talk for a moment on the business side of the House. Now there’s a business, right? Your marketing and sales guy. So you have to have a product. You have to package that product. You have to have a marketing engine. You have to have a sales system in cycle. So how did you go from being, you know, sort of marketing and sales to being, you know, the SVP of marketing and sales for the product that is you. Talk about that for a moment.

Thom Singer And then you hit it right on the bucket. Is that I was the product and I had been selling I’d worked in law firms and consulting firms where I was selling people as a product. But it was other people. So it was really hard to go to that marketing myself, calling people going, hey, I’d be really good. So a lot of it what I found was it was word of mouth and it was networking and it was reputation built. And fast forward 11 years. Now I have a better product. I’ve done a lot more. I have a certainly reputation. It’s still word of mouth networking and reputation that gets the business. So a lot of it is the more I spoke, the more people saw me and would say, hey, that was different than I thought it was gonna be. We should have you come into my company. Would that work for a group of accountants? And so.

Peter OK. But I want to I want to argue with that because there are many speakers. Most I would say that do get a lot of their business, meaning the more I speak, the more I speak. Right. Every time I go out, whatever. I would always argue their bit. That’s OK. That’s all fine and dandy. But what are the systems and processes that you have in place? Pre-speech at the speech and post speech to accelerate or increase the probability of that happening. Right. Cause there’s always going to be, you know, the five people at the end that’ll wait in the rain or whatever to go shake your hand and all that sort of stuff. And listen, maybe those people do book you. But how do you optimize that? Well, people speaking, as does processes that.

Thom Singer There are and I wish I could tell I was great at it. And I kind of suck at it. Originally, it was an Excel spreadsheet. Now it’s a CRM. But so part of it is, is that, you know, it’s creating that touchpoint and follow up to people who maybe didn’t book me last year. So a lot of speaker fall into the thing that maybe it is word of mouth and reputation. And really, if I go and look at my last 50 bookings, 40 of them came from someone saw me and hired me. I mean, it really did for me. It really has been that way. But sometimes.

Peter If even if – even then that someone saw you.

Thom Singer In my life five years ago. Yeah,.

Peter No. But even knowing that. So I want to get a little bit granular. So someone saw you. So let’s say you did 50 gigs last year, 300 people in a gig, whatever the math is on that. A lot of people write 50. That’s right. Right. What are you doing to ensure that people know you’re available to do this? What are you doing to collect their information, collect their e-mails? Stay in touch with them at all? You walk through sort of your system vibrating, wishing you to speak a week from Tuesday. What would I expect and then not speak?

Thom Singer So I usually don’t get to collect the whole audience email because the type of places I work for I work aren’t in that list. Don’t want me peppering their people and things like that. So a lot of it comes down to who am I connecting with on in person or in social media who were there? And then it’s trying to get them into that thing. But for me, a lot of it has to do. I mean, and maybe I just am lucky, but a lot of it really has had to do with having a conversation afterwards where somebody says, OK. Will that work for my company? Now I’ve got their card. Now that I’ve got them, now they’re going into my CRM and I’m going to constantly drip on them. And some of these people who book me, it is five years later. And so it’s keeping the show.

Peter But I want to decompose that. So if we’re even. So if we can’t get their information and I get that a lot of you know, if you’re going into a company or association, they won’t do it. Now, there are ways, there’s some tricks that you can increase that whatever. But now let’s say it’s the end of the speech. And you had four or five interesting conversations with Sally and Joe and Bill and whatever. There are two types of speakers. One. One takes those cards, puts them in their jacket pocket. And then three weeks later, when they take out the jacket, they go, yeah, it wasn’t Denver three weeks ago. Right. But it seems like you’re disciplined to say, now I’m going to take that information, get it into my CRM. That’s going to trigger a welcome aboard email. So what exactly what are you dripping to them in what cadence? Because I think this is the part that people have a hard time with.

Thom Singer So doing with the macro, the small, the micro excuse me, the small touches. If I’m getting a card and having a conversation, I send a handwritten note to everybody citing that conversation. That’s my first touch. And I will do that with 10 to 20 people after an event.

Peter I will send within what time frame will I get that is within a day or two. You like that?

Thom Singer You’ll get it within a week. I mean, I would do it sometimes. I travel with cards. My wife’s real good about saying gift cards in your bag for the plane. And while I’m on the plane, I’ll just book.

Peter So that’s great. But we had a conversation and we talked about, oh, when you told the story about global blah and that really you’re making a mental note and that’ll be in a personal touch, a card. Right. So you’re standing out, OK?

Thom Singer And if there was a legit, either they said we could hire you or I know based on where they work, they work for a large association. I will then follow up a week after that card with an email that basically says, hey, when we talk or it’s my assumption that that’s who do I need to talk to within your company to be able to be able to have that.

Peter Good. And I said, listen, it could be five years, right? And then what’s the drip, drip, drip that they’re going to get? So that’s a specific personalized touch point based on the interactions and the conversations, et cetera. Then what happens?

Thom Singer So I used to do a newsletter regularly, but I really wasn’t getting that much out of it. So now I have what I call an occasional newsletter. So they’ve done it – newsletter thing. I tried to get them connected. If they’re a social media user, I try to get them connected through whatever they use. And then I’m pretty active on all the social media channels. I’ve literally had people hire me in the last year and I say, oh, how did you hear about me? And they said, Oh, I follow you. You know, we met at a conference five years ago or somehow they crossed my path. But I follow you. You do a good job on Twitter or whatever. I don’t think I do, but a lot.

Peter But you you’ll track them down because you’re going through this quickly because you’re so good at it. But I want to I want to make some nuggets. That’s what you get. So then we’ve gone through this personal touch. You’ve then tracked them down on social. You have some tools that can do that and say, I’ll connect with them on LinkedIn, connect with them on Twitter, whatever. You’re consistently putting out good content there. So you’re staying top of mind. Right. Anything else? More personal? An e-mail one to you. Like what? What I’m trying to understand the cadence and the mix of touch points. I’m going to get.

Thom Singer So I wish I could tell you I was really good at this system. My goal? I suck at this. And that’s why I said maybe I’m just lucky because I know there’s a lot of people who live and die by their systems. I I tried to. Now that they’re in my CRM, I always when I have a touchpoint, I will schedule like four months later. Three months later,.

Peter OK.

Thom Singer Email them again. So every couple times a year, if you’re in my world, you know, hopefully it’s going to pop up and I actually spend some sort of a thing. Occasionally I’ll call people if I if there is somebody who I should be there, like I know who they’re speakers were the last three years and they totally could hire somebody like me. I may call. But yeah, I’m not I don’t have a great system. And maybe that’s why I’m not making a million dollars a year. I’m not I’m not as organized as I should be. I did have a sales person working with me for a while. Right. Because he was like, bam, bam, bam.

Peter Yeah.

Thom Singer But again, it’s just it’s a hard business. It really does come back to word of mouth. Now, part of that is you can start the word of mouth by reaching out cold to them or true onto a list. But I find my goal isn’t to get them to hire me to speak. My goal is to get on their short list, because in reality, sure, I have found over 10 years or 11 years that if you really talk to me, you have a keynote. You need a master ceremonies. And you’re serious that I have made the cut of one of those three. You’re gonna talk to. I will usually win. Not always. But it’s something like I last year looked at all the real proposals I was.

Peter So let’s talk about that. That’s interesting, because oftentimes, listen, you know, you’re looking at you’re looking at somebody else. Right. Also most of the time. Right. And then you’ve got to know. You know, I think there’s a couple of things. Oh, I always go up against so-and-so or this one I’m going to win because. Right. So I think sometimes people are looking at it and comparing apples and apples. Right. You know, you’re not Malcolm Gladwell. Right. So it’s not a choice between you and him. That’s a different level of. It goes by. I mean, you know, price point. Right. You know, the style of event. You know, the type of speakers. They might have one. So why do you think you’re winning in the bake offs? Right. Because they’ve got you and three other people theoretically equally qualified and theoretically, they are kind of similar.

Thom Singer By the time they get to that, they’re going to be similar. They’re going to be in those areas. Once in my life, I went up against somebody that was out of my league. It was me and Biz Stone, the founder of Twitter. Yeah. And his fee was twice my fee. And the whole time I was going through this dog and pony show, that was like three calls. I could never figure out how it came down to the two of us. And they ended up at the last minute picking him. And I wasn’t surprised at all. If they had a twenty five thousand dollar budget and they wanted a celebrity, why was I even there? Right. Right. But in most cases, I’m up against a peer. I don’t ever run into the same person over and over. I just don’t. It’s rare that in a year I’ll be down.

Peter There are some there are some speakers where not often where it’s a little bit of Coke and Pepsi. Right. You know, this one goes against that. OK. So, you know, you’re basically going by price point and probably reputation of the other speaker style.

Thom Singer Yeah. You know, it’s usually going to be a high energy speaker who’s talking about a business, soft scale. Sometimes our topics will be like night day, but it’s still business, soft skill topics. So and I think the reason that I often do well is that I really I consider myself not just a speaker, I consider myself part of the meetings industry. I’ve been involved with, you know, the different meetings organizations. And I think that I talk their language. I mean, I think when I talk to meeting, I’m married to a meeting planner. She works for a large association. So, I mean.

Peter OK. Wait, wait, wait. That’s that’s a point. Get fired. Marry a meeting planner.

Thom Singer That is true. That’s a good call. We could have shortened this. So let’s talk about that. So oftentimes. Speakers are, how would I put it? There’s two masters that you have to serve as a speaker. There’s the button to see, right. And I think most speakers really, really get that. And sometimes to a fault, because many of those participants, the audience members, they’ve been Volin told. Right. Didn’t opt in to go. I work for Oracle and there’s an Oracle sales conference. I got to be at something such a place at 10 o’clock on Tuesday, whether I like this guy, Tom or not. Right. That’s just they’re serving chicken meat and chips. You know, then there’s the buyer. So if you go to the meeting planner, what are the things that keep them up at night? So I think obviously, if you wait for me to play it, you really tuned into that. What are the things that you do to make give them comfort? Because I think a lot of people don’t realize that they’re sending contracts with ridiculous requests to buy only travel, you know, first class. I need my room to be seven steps from the elevator and all that stuff. How do you make a meeting like planner’s life easy?

Thom Singer Well, I like to believe, first of all, is that I show up early and I stay late. So a lot of speakers, their greatest skill is getting to the airport 20 minutes after saying thank you. So I came up with this term that I was the conference catalyst. And part of that is that I’m gonna have help. You have the best event ever. And it is true that a large chunk I don’t I’ve never done it scientifically. So I know what to make of a statistic, but a lot of them could care less. A lot of speakers don’t care that I’m going to say a lot of don’t want me to stay. However, there is a swath of them who are like, you mean you would stay through lunch? And I’m like, yeah. The guy speaking at 8:00 in the morning. But we have a networking lunch. You would come to that? And I’m like, of course. And I go, we’d never had a speaker agree to stay. We always ask or we stay through the evening and emcee our awards dinner. We don’t have a budget for it. I like that. And they’re all they pay for the extra hotel room. I’ll do it. I mean, my thing is my I try to say, yes, we do a breakout. I don’t charge more for a breakout. And I’ve had other speakers get on me going, oh, you charge three grand more. I tell them straight up, I’ll do a breakout. No extra charge because I’m there for the day. I’m yours.

Peter So let’s talk about that mindset, because I think what you’re hitting on a huge point and a lot of speakers don’t get it, which is there’s one speaker that does the drive by. You know, the plane lands at 10:00 o’clock. They’re on at 11:00 and they’re back at, you know, the 2 o’clock flight. And by the way, the meeting planners know that. Right. And they whatever you’re doing your job and you’re performing well or whatever. But if their job is to make this conference successful, you’re saying I’ll go to the networking event. What else can I do to make you successful? I’ll see it whether you’re getting paid or not. That’s a separate conversation. But I do like the mentality. Listen, I’m there for the day. Like, it’s not like you’re flying home to do another gig that evening. Right. And that level of generosity leads to relationship development, leads to them going at the end. Well, you know, that Tom guy, that’s he’s a good guy. He really was helpful. And it may or may not even be so much the stage chops, but you’re one of us. So you really, really went out of the way to do a good job and help us out there. I think that’s a great point. And how would you say that has. What’s been so crazy like the ROI in that? In being a good guy?

Thom Singer Well, I think that, you know, again, it has to do with my topic is too right. I started speaking about how do you connect with people in a gadget crazy world. Eleven years ago, we got our what he called smartphones. Right. And everybody stopped talking to each other. Yeah. And my message is, here’s how we maximize a live event. Here’s why networking actually matters. And it’s not put your name tag on this side and shake hands strong. Yeah. Yeah, that. So part of it is, is because down the damn phone, look me in the eye and I take that message and I literally halfway through the keynote go, hey, I have an idea. What if we make this conference a human laboratory? What if you put some of this in as soon as mine’s over and we go to a coffee break? So the other thing is, the way I structured my topic, I wasn’t a networking speaker. I was the conference catalyst. Yeah. Giving them things to take to their career, which is what all speakers do. But we’re going to implement it on site. And meeting planners would come to me and say, this is a tech conference. I’ve got five hundred CEOs and nobody has their phone out at the coffee. What did you do to them?

Peter Yeah. Right.

Thom Singer And then they’d be like, well, we have to have this next year. So that’s how I became a master of ceremonies as I took the keynote. Yes. But up in the seven minute slots. Yeah. Now I can do it over three days as the master of ceremonies helping make their event better. That’s my love than ever.

Peter Yeah. Well I love that you’re doing experiments in real time that have a real tactile response. People know when they’re in an event. If people are actually, you know, like the good old days before smartphones where during the breaks we actually talk to other humans versus use that, you know, there used to be biobricks, others tech bricks. Right. That’s right. Interesting. Great. Well, this has been fantastic time. Any final words of wisdom to someone out there now who’s about to get laid off? Or are you 10 years ago?

Thom Singer To 20, 20? Well, first of all. Now, you know, there’s no life events. I mean, my entire calendar has been cleared from March to May because the Corona virus. So now is probably not the time to say you wanna be a speaker because there’s nowhere to speak. But this, too, will pass. Live events aren’t going to die. There’s a lot of talk that we’re gonna go virtual. There will be more virtual. But life events aren’t going anywhere. So when it comes back, if this is your calling and this is your dream, two things. You got it. You said it to begin with. You got to be great on stage. And, you know, I hate to say that because then I’m saying I’m great on stage, but you have to. And you can’t determine it because people tell you you’re good at it. You determine it because people hire you after they’ve seen you speak. You know, if they say great speech, they might be saying that being polite, if they say, what else can you do for me? Then they really liked you.

Peter That’s the ultimate compliment.

Thom Singer Right. And so if you’re good, you should spend business. The second thing is, is that it takes a long time. It took me three years to get back to a corporate salary of what I was earning, you know, as a director of marketing on that. And then the last thing is there’s gonna be ups and downs. You have to be a sales person first. If you don’t like sales, you cannot outsource it. Everybody wants to hire some.

Peter Yeah, somebody will do that for me.

Thom Singer Get a bureau to discover them if you’re not a famous person. I love speakers bureaus. I get book by two or three a year, but I don’t get booked by 30 a year. Yeah. I’m just some middle aged guy who tells some good stories on stage that doesn’t fit a niche for a speakers bureau. Sure, they don’t. They don’t book me. So I have to be constantly trying to put myself out there and just yeah, I try to be the nicest guy I can and I’d still believe nice guys finish first.

Peter Well, there you go. Well, thank you so much. This has been great. I appreciate all all that we unpacked together here. There’s a lot in there and a lot of a lot of wisdom and a lot of stuff that people can take home and actually do something. So thank you so much.

Thom Singer Thank you.

Peter Winick has deep expertise in helping those with deep expertise. He is the CEO of Thought Leadership Leverage. Visit Peter on Twitter!

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