Lead. Care. Win. With Your Speaking Business with Dan Pontefract

Colorful heart image

Dan Pontefract just released his new book, Lead. Care. Win. and it became evident that Dan has used this framework to help build his speaking business. 

At an early age, Dan Pontefract always saw himself of the stage, but then soccer and girls took over his time in high school. It wasn’t until he graduated from college that he went into education. He went from education into higher ed and then into the corporate world, and then launch his own business. Every step along the way, Dan has used is curiosity to help others by leading, caring and ultimately winning for the people he educates and for his speaking business. 

Other insights in this episode of The Business of Speaking:

  • Understanding the different types of talks and how you should approach them differently
  • If you can, give yourself a long runway to hone your craft
  • There are some similarities between education and speaking but giving a keynote requires a different approach
  • Don’t rely on just speaking – look at how to diversify your revenue as you start your business
  • Look at your area of expertise, that gives birth to being a speaker, author, etc. on that topic 
  • Be ridiculously curious and see who you can learn from by asking questions about their processes
  • You can’t please everyone, and that’s OK

If you have trouble viewing the video, check it out on YouTube. Be sure to subscribe to our YouTube Channel and get notified when new shows are added. 

Who is Dan Pontefract?

Dan Pontefract is the founder and CEO of The Pontefract Group, a firm that improves the state of leadership and organizational culture.

He is the best-selling author of four books: LEAD. CARE. WIN., OPEN TO THINKTHE PURPOSE EFFECT and FLAT ARMY. A renowned speaker, Dan has presented at four different TED events and also writes for Forbes and Harvard Business Review. Dan is an adjunct professor at the University of Victoria, Gustavson School of Business and has garnered more than 20 industry awards over his career.

His third book, OPEN TO THINK is the 2019 getAbstract International Book of the Year winner and the 2019 Axiom Business Book Award Silver Medal winner in the Leadership category.

Previously as Chief Envisioner and Chief Learning Officer at TELUS—a Canadian telecommunications company with revenues of over $14 billion and 50,000 global employees—he launched the Transformation Office, the TELUS MBA, and the TELUS Leadership Philosophy, all award-winning initiatives that dramatically helped to increase the company’s employee engagement to record levels of nearly 90%. Prior to TELUS he held senior roles at SAP, Business Objects and BCIT.

Dan and his wife, Denise, have three children (aka goats) and live in Victoria, Canada.

You can always find Dan Pontefract on Linkedin, Twitter, Instagram and Facebook. And don’t forget to check out his website


Want to receive exclusive content not available on The Business of Speaking Show or blog? Subscribe to our weekly newsletter. 


Title card for Lead. Care. Win. with you public speaking with Dan Pontefract

Below is the full transcript from the show with Dan Pontefract. Please note that there may be some errors as it was auto transcribed using Otter.ai. (referral link that provides us with a 1-month Premium Pass

Tim McDonald 0:00
All right. Well welcome everybody to this business of speaking show. I am your host, Tim McDonald. And today I am so fortunate to be joined by somebody that I’ve had the pleasure of knowing for several years now and just got to work with him on a project early in 2020 called SpeakAid 2020. Dan Pontefract, how’re you doing Dan?

Dan Pontefract 0:19
Him, Uncle Tim, brother Tim, Tim, it’s so good to see you. It’s so good to be on your show, I’m so thrilled to be able to impart any type of experience or wisdom or knocks that I’ve taken in this the business of speaking but more importantly, Thanks for the invite, you are an amazing human being and had been for for your life, obviously. But since I probably met you in 2014, ish, I think somewhere around there.

Tim McDonald 0:43
I think that was right around the time of, of when your first book, I think was coming up Flat Army. So um, you know, and for those that might not have watched this show before, really what it is, is, it’s not to focus on what the speakers talk about on the stage, but their journey on how they got started to the stage and what they’ve learned since they’ve been up on the stage. So if you are thinking about getting started and speaking, are just starting in speaking, or as 2020 has taught us, no matter what you thought you knew about speaking, we never know what what the world has planned for us. This is a show for you and a community for you. So with that being said, Dan, I’d love to kind of kick off with, you know, telling your story of how you got started in speaking.

Dan Pontefract 1:35
Wow, well, I believe I was potentially put on this earth to be on a stage, or more importantly, what I just called in front of people to help. And when I was a kid, Tim, when I say kid, I mean sort of in my 12 to 16 year old self. I was on stage in plays. You know, I was Tom Sawyer. I was Huck Finn. I was in all sorts of different things that in Hamilton, where I grew up in Ontario, and the theater was something for me, where I could unleash, I suppose my desire to be creative in an artistic form in front of people. Now I was an athlete, and I was an academic, there’s a sort of like a third dimension to me, and I really enjoyed it. But then kind of when I turned 16, I got really heavily into soccer, and girls and work at the grocery store. And so it sort of took a backseat. In fact, it just disappeared. But what ensued over the following years was this penchant to help. And ultimately, I ended up at McGill University in Montreal, I thought I was going to be a doctor and or physiotherapist, I ended up being an educator. So I got my BA, I got my BE, bachelor of education. And I knew that that was a way for me to help but also kind of be on stage. So Denise, and I, my Incidentally, better half, and I picked up on a Montreal got married, moved to Vancouver, and became a teacher of high school for about two years. And it was lovely, you know, because every day, we were kind of on stage, if you will, helping, so it kind of married these two ideas of mine to be on stage to help so but I realized then as well, after the second year that maybe there’s more to helping and if you will, speaking then just in a classroom with 20 to 30 kids. So I went into higher ed. And in higher education for about five years, is again a different audience, but still in front. So I’m a director of a bunch of high tech professional career changing programs, cohort based model. And you know, I on Friday afternoons, I’d be able to what was called facilitate open dialogue about how things are going in their program, their lives, their career changes, etc. And it was a lot of two hour sessions of extemporaneous. Hey, what you doing? How can I help and weaving in stories? So then I entered into the corporate world, switching from education and higher ed into the corporate world, Tim, and it was then in 2002, where as a chief learning officer, I started delivering talks. And those talks were in conferences, right, it was in the organization. And that was in 2002. And then by the time I joined a telecom in 2008, I was now kind of quote, I would say on the circuit, and the circuit becoming, I was the kind of one of those guys that people would ask me to be at these conferences, to speak about Learning and Leadership and education, and culture and engagement. And so it really, it gave me a long runway to fixing and honing my craft which ultimately became my business or at least part of my business. Right around Say yeah, 2013 2014 when we met, and the book started coming out, and I complemented books with speaking with consulting, and that’s where I’ve been doing for the last five or six years.

Tim McDonald 5:11
Yeah, no, it’s I’m just always curious, because I’ve heard a lot of speakers have been in the classroom or, you know, at one point before they actually started doing speaking professionally, outside of the classroom. And I’m just kind of curious, was there a different feeling for you when you were getting up on stage? You know, not in front of a class, but in front of a different group of people that maybe you didn’t know?

Unknown Speaker 5:36
Yeah. Well, there’s, there’s different types of talks. I don’t know if we’ll get into that. But you know, there’s the keynote. There’s the sort of facilitated dialogue chat, if you will, sometimes fireside chats sometimes, you know, panels, right, and you’re still on stage. But then there’s, yeah, there’s, there’s times in which I would still call it a talk, you’re speaking but it’s more an extemporaneous, you know, massive coaching call. And it’s, it’s me, or whomever engaging with the audience, as if you’re doing a bit of off the cuff stand up, like how stand up comics might do when they engage with the audience, and they make it really funny. In these cases, I’m making it more of a coaching conversation with an audience. So first of all, I’ve learned that there’s different types of talks for sure. But you’re right, the question about, you know, coming from a classroom, or even, like I taught phys ed for a while as well. So you know, big classes of 50 to 70 kids and large gymnasiums, or pitches or field grabs, right? It’s different, obviously, because, in some cases, if you’re doing the formal keynote, let’s say it’s 45 or 60 minutes, you better have a plan to do a good intro, make sure it’s a good story, you know, make sure that there’s some levity, some self deprecation, and then you better have some sort of arc. And then a conclusion, whether you’re making them cry or feel good or both. You know, that’s, that’s a different art than the lesson in teaching, but getting up on stage, and being able to do it and know when to look at people in the audience know when to take a break. And when to pause, you know, when to rise and up and down with the emotions of the room, that’s a that’s a classroom technique of To be honest, and I’ve taken that those classroom techniques or gymnasium techniques and put that on the stage.

Tim McDonald 7:29
Now, that’s, it’s pretty interesting, that, you know, there are certain things that we need to still learn as we get into this. Now, I know, you know, when you work for a corporation, and you have the opportunity to get out and speak in front of whether it’s teams employees, or you know, in industry, you know, events, you know, you still have the comfort of having a paycheck from your employer. What made you or when did you know, it was right, for you to kind of embark on this on your own instead of having that kind of guarantee of a paycheck?

Dan Pontefract 8:06
It’s a great question. One. It’s a question. I think, Tim, that I’m often getting from folks that are working in, in organizations, be it public sector, not for profit, or obviously for profit corporations, you know, you’re it’s, I have been privileged, quite frankly, to have been able to be remunerated for many years by you know, high tech company by a telecom company and and hone that craft if you will, of becoming getting on stage and not having to worry about what I’m charging for a keynote or or not. And how many keynotes I could do pro bono, they were all pro bono. That’s just how it was. So I guess, you know, Dorie Clark, who’s a dear friend, and also just an amazing guests, as you probably have on the show, you know, Dorie, long ago had figured out how to have income streams, varied income streams. And so as much as I believe that there is a lot of goodness, and, and, and heart and giving that comes of speaking, I don’t think it can be the one thing that you do. I think that there are there is a need to have multiple revenue streams, if you will, if you’re about to go out on your own. So for me, you know, revenue streams of speaking in my if I look back in 2018 2019, halfway through 2020 or so, speaking is about a third of what I do revenue wise, it may not be a third timewise because it ebbs and flows. Sometimes I’m going to spend a lot of time on new material on ways in which to help a particular client so even though it might be a one hour keynote, it’s about 30 hours of work to get it right and then to practice it, right. But other times there there are keynotes where I know That I’ve delivered it perhaps one way for one client or a conference, I can tweak it. And then, you know, do it slightly differently, but not spend as much time. So the point being is that it’s about one third of revenue. And the other two thirds of my revenue streams are things like writing or things like coaching things like consulting, things like doing assessments and so forth. So, again, it’s a long winded answer. I’m sorry, Tim. But if I’m asking, if someone’s asking me, what did you do to get into the speaker world? Well, I didn’t just think I was going to be a speaker.

Tim McDonald 10:34
No, I think that’s very valuable and very helpful to so many people. Because, I mean, that was one of the things I had thought when I was gonna do it was I just wanted to be on stage, you know, and I’m still trying to figure out that that element of it, and I know a lot of other people will be too. So one thing that that I’m kind of curious about, because I see so many authors writing books, and so many speakers are, you know, do you call them a speaker? Do you call them an author, right? Because they’re both up on stage. So what, how do you view yourself and how did they both complement each other,

Dan Pontefract 11:11
uh, I am an author, I am a speaker. But first and foremost, I’m an I’m a leadership strategist. And the leadership strategist, insignia, if you will, is one that gives birth to being a speaker and author, a coach, a consultant, a learning designer, for all the online learning courses and things that I’ve built. Those are almost the outputs of being the leadership strategist. So So my job is to sort of say, look, Dan has ways in which he can support you, I’d love to be on stage. I mean, it’s great, I’d love to be in a facilitated workshop with 20 people online or face to face, I’d love to go into your organization and just sit with employees and listen to their stories, and understand how the culture is going on. I’d like to go in and help you build out a learning program or a leadership model. So whatever your thing is, your expertise, in my case, it’s leadership and culture and engagement and people in organizations and org design. I just call myself a leadership strategist. And then how I, how I deliver on that expertise comes in those either revenue streams, or channels or verticals, whatever you want to kind of think of them as, so if you’re a an expert in CPG, or the retail industry, you know, maybe you want to call yourself a retail strategist, or you know, a retail thought guru or whatever, I don’t really care. but you get the point, right? It’s what’s your expertise, and then go from there on how you can deliver modes of excellence so people can can learn from you.

Tim McDonald 12:55
Yeah, and, you know, you mentioned that you add a lot of different revenue streams built in from the beginning, when you launched out on your own. did was it obvious what they were? or How did you kind of figure out which revenue streams were going to be the right fit for you?

Dan Pontefract 13:14
Wow, I suppose Yeah, to each their own, because there are some dear friends of mine that probably have a 90% revenue stream on speaking and sort of 10% other, so it just sort of fill your boots depends on your fancy. And I’m not knocking folks that are doing all speaking all the time as their mode of revenue. What I did was I looked at myself and said, Do I want to speak all the time? And and that was a an answer that I often said no to. A) three goats were raising Denise and I lots of travel, obviously, it’s mitigated a bit to a degree with the pandemic. Well, it’s mitigated a lot, isn’t it? But that’s kind of where I’m going with, right. It’s a it’s an opportunity for you to say, what’s the right mix? And if your speaker x, whom wants to speak at 90% good on ya, but if you’re someone like me, who believes that, you know, there’s perhaps more ways in which for you to address your talent as a quote, leadership strategist, then, you know, you might, you might have to kind of mess around a little bit to find out what the right mix is. And again, I’ll say this, Tim, like, we all have rent to pay and mortgages to pay and groceries to pay and school clothes to pay for and so on. Right? So I’m not saying that you shouldn’t take on more speaking gigs if it’s going to help you get to the right, I guess, repertoire the mix. So don’t don’t hear me as if I’m being pompous and saying, Oh, you should do it. This. No, you got to do what works for you to pay the bills, right. But if you can get into a groove eventually that allows you to say I want to do 20 keynotes a year. And those 20 keynotes, I know, are gonna revolve around 20 times three, three days, because it’s a day to travel ish, maybe it’s two days, maybe it’s a day of prep, right? And kind of, you know, eight or nine hours of content, maybe your formulas four so, so it’s four times 20. That’s 80, 80 days of a calendar. And, you know, that’s, that’s a lot of time. But that could be you looking at saying 20 keynotes equals 80 days. Okay, that’s just about a quarter of my working days. That means I’ve got 25% of time and revenue dedicated to the 20 keynotes, what am I going to do with the other 75? or How can I compliment it, maybe you start out with, I want to do 60 keynotes, maybe you want to because you want to get there, you start at 20. And then you get to 40, get to 60, or five year plan, whatever it is, I’m a math guy, like one of my minors was math. So I always look at it so mathematically and say, How am I going to spend my time? And how do I want that pie graph to look, as I’m building out my repertoire of skills.

Tim McDonald 16:04
Now that’s very good, very good. You mentioned Dorie Clark as one of the people on so I’m just going to curious, I it sounds like you’ve had influences and people that have helped you along the way. What had been your biggest resources for, you know, really evolving and growing your business?

Dan Pontefract 16:27
resources? From a resource perspective, I think being first of all, a an autodidact. And a ridiculously Cur-curious person has helped me in my sort of lifelong journey. definition. And that That, to me is everything about who I am today, I am ridiculously asking questions about people about process about how tos about how did theys. And all of that goes into my head plus Evernote and I kind of attack it, I tact I write down a lot of little pointers. So I may, you know, someone, someone sends me a TED talk, and I’ll look at it just to see style content, you know, storytelling, what have you, if I were kind of talking about speaking here, when I’m at, if I’m asked to speak at a conference, you know, I’ll try to be there for the speaker before or the bit of the speaker after to get to see and hear and feel and smell what that style is like, both the good and the bad, and a sense of what I would do what I wouldn’t do, right, the good for me, the bad for me, because my style is one that’s different, but I could learn and maybe hone in a little bit. So there’s particular people that have done an incredible job of just speaking. And I’ve learned from that, and I again, whether videos are face to face. But similarly, you know, whether it’s Dory, or lots of great folks that have done the incredible job of building up the repertoire of options, I find, I find like I’m no one when I look at them and see what they’ve done. But that said, it’s pushes me and kind of my continuous addiction to improving myself to see well look at how they’ve done it. Maybe I could do that this way. Another dear friend, and example is Michael Bungay Stanier. So he author of the coaching habit and the advice trap. So Michael and I go back longer than you and I probably to 2010, probably 10 years now. And MBS, as he’s affectionately known, as you know, helped build up a company called Box of Crayons that helps people essentially become better versions of themselves. It was kind of a learning and development company and then it turned into a kind of leadership development and a coaching company. And he built this up from nothing, all the while writing I think he’s at his six books now. And also speaks and facilitates and and builds out these learning modules and it’s just he’s I’m in awe of Michael and his ability to build out the repertoire all the while being an engaging and funny Yeah, heartfelt speaker when he’s on stage. So I think we’re I look at myself as being in the vortex and shadows of the doors and Michael’s learning from them and trying to find ways in which to weave that into what I’m what I’m doing.

Tim McDonald 19:28
Now. I can’t believe our time is just flying by but one question I had before we kind of get into wrapping up is knowing everything that you know now. And I you know for most people I can say go back to when you started speaking but I know you started probably back when you were in your teens. So back when you were like kind of in the corporate world getting ready to think about launching on your own. What advice would you give yourself that you know now to that younger self of Dan

Dan Pontefract 20:03
What a great question I would, if I’m looking back at myself and saying, if you were to do it differently, okay, here’s the best way I would describe this is the audience is like a classroom. And when you’re a teacher in the classroom, unfortunately, you’re not always going to reach everyone. And whether it is a personality thing, or it’s a learning thing, or it’s a distraction thing, or it’s just, I’m an interested in you thing, or the content. Inevitably, you will receive like I did as a as an educator, as a teacher, as a prof you receive evaluations. And when something happened with me, for some reason that I thought all of a sudden, now you’re in the corporate world, you’re in corporate conferences and events, the evals are gonna be smokin hot 99%. This guy’s awesome. Because he’s funny, he’s engaging. He’s on stage, look at his hats. Look at those shoes, what great shirts, like it’s a different, like, you’d kind of you do a little bit of a persona change, at least I do to pay homage to my my buddy Gore Downey, of the of the hip here in Canada. And what I recognized was that the audience is a lot like the classroom in that you are going to get all wild differences of opinion in the audience. And then when you kind of go back to the evals, you are going to get some haters. And the haters are like, this guy’s an idiot, why is he wearing a hat? You know, why is he telling me how to lead I know how to lead. And again, you can’t focus on the five or six or X number of negative Nellies that are out there. because that’ll that’ll get you weirded out. And unfortunately, Tim, I think I was weirded out for the first few years. Because I would get those and think, Oh, my God. And it wasn’t until two or three or four, maybe five years into sort of the circuit and conferences, etc. I realized you can’t please everyone, Tim, in an audience. And that’s okay. So that’s my, that’s my lesson to myself. If I was kind of looking back and speaking to a younger Dan,

Tim McDonald 22:25
well, thank you. And I know you have a new book out Lead, Care, Win. I’m just kind of curious, what was the kind of the inspiration or the thought for this book.

Dan Pontefract 22:37
I have one copy, Tim, a lead care when how to become a leader who matters is a book that it just, it sounds horribly pretentious and arrogant, but it had to be written. And the reason it had to be written was that I’ve just come across far too many organizations and employees and leaders whom have sort of somewhat somewhere along the way missed the plot on what leaders are supposed to be doing. And so there are nine behaviors that I make reference to in this book that resurrect this is nothing new, it resurrects what a more caring, empathic, concerning type of leader ought to be doing both leader of self and leader of others. And it just to me is one of those where we need to be more patient, we need to be better listeners, we need to build relationships and champion others, we need to be the Curiosity based individual, you know, we need to commit to balance with equity, diversity and inclusivity. They’re just it’s a book that is resurrecting all of the goodness that has come before us into a compact nine lesson, Field Guide to remind people how important is and what to do to sort of take them back to where it ought to be. LeadCareWin.com is easiest way to go find out about that book.

Tim McDonald 24:05
Well, fantastic. I’m looking forward to reading it because I just got my copy. So tell everybody where they can find that book and how they can get in touch and learn a little bit more about you.

Dan Pontefract 24:16
Yeah, well, thanks so much again, Tim. It’s a pleasure to be here. Again, you’re such a good friend. The the book itself is available anywhere. So it’s, you know, go online, visit a local bookshop, get them to order it if it’s not there for you. Love to support your independent bookshops. Yeah, lead care when.com. Best way to go there. From there, you can kind of get some BIOS about me and find out what I’m up to. And what I’m really excited about the first time I’m releasing an entire online leadership development program with the book. So it’s a it’s pretty compelling. There’s about an hour of core material for each of the nine lessons and then upwards of two hours of bonus material on each of the nine lessons and it’s It’s been a treat last three months putting this thing together. So looking forward to releasing that as well.

Tim McDonald 25:04
Well, thank you so much, Dan. And thank you for watching and tuning in with us today. Again, if you’re new to the show, one thing that we do is we stop the broadcast here in just a minute. So, but I have a special surprise for any of our email subscribers because Dan agreed to stay on with me and answer one additional question. So we’re gonna record that but not put it on YouTube. So if you want to get that information, head over to business dot speaking or speaking dot business, I’m sorry, I’m like the business of speaking show. But speaking dot business and sign up for our free weekly email newsletter and that’s where you will get this exclusive content. So thank you for for watching today. And thank you for joining us, Dan.

Dan Pontefract 25:51
Oh, so good of you Tim. Thanks, everyone.


Leave a Reply

Your email address will not be published. Required fields are marked *