Start With A Win - Jonathan Bennett: The #1 Job of a Leader is to Replace Yourself

Episode Date: October 15, 2025

In this episode of Start With a Win, Adam Contos sits down with Jonathan Bennett, a seasoned executive, advisor, and coach who has walked the path from building a thriving consulting firm to reinventing his career with deeper purpose. Together, they peel back the curtain on what most leaders avoid discussing - transitions, fulfillment, and the hidden weight of leadership. With candor and insight, Jonathan shares stories of growth, reinvention, and the art of truly listening - offering a rare window into the challenges and opportunities that come with leading at the highest levels. This is a conversation that will make you pause, reflect, and rethink how you define success and leadership in your own journey.Jonathan Bennett is an advisor and executive coach for purpose-driven leaders who need help solving their organization’s toughest obstacles. With experience in urban, rural, remote, and First Nations communities, Jonathan’s expertise is in social purpose business strategy, governance, branding, change, and communications. His coaching draws on 25 years of creativity and leadership success as a CEO, board member, and founder, and he is known for his deep-listening and his breakthrough solutions that create insights and new strategies.00:00 Intro01:59 A single aha moment…03:56 Oh no who is leaving…do you have this in place?07:05 I spotted these core competencies and knew this person was the next CEO!10:55 Need to go on this journey to get unstuck.15:25 How can leaders benefit from listening however not just listening but this! 20:25 Are we wandering or focusing?24:25 Start not here but here for this management!  https://clearlythen.com/===========================Subscribe and Listen to the Start With a Win Podcast HERE:📱 ===========================YT ➡︎ https://www.youtube.com/@AdamContosCEOApple ➡︎ https://podcasts.apple.com/us/podcast/start-with-a-win/id1438598347Spotify ➡︎ https://open.spotify.com/show/4w1qmb90KZOKoisbwj6cqT===========================Connect with Adam:===========================Website ➡︎ https://adamcontos.com/Facebook  ➡︎ https://facebook.com/AdamContosCEOTwitter  ➡︎ https://twitter.com/AdamContosCEOInstagram  ➡︎ https://instagram.com/adamcontosceo/#adamcontos #startwithawin #leadershipfactory

Secession planning is the thing about which nobody wants to speak. You know, what I like to say around board tables, especially when I'm doing consulting work around board tables, is like denial isn't a strategy here, folks. Like, let's, you know, there's a hundred percent chance that your CEO is going to leave at some point. Welcome to Start with a Win, where we unpack leadership, personal growth and development, and how to build a better business. Let's go.

Have you ever built something successful and still felt like something was missing? Today, we talk about that on Start with a Win. Coming to you from Area 15 Ventures and Start with a Win, headquarters, it's Adam Contos with Start with a Win. Jonathan Bennett left a high-level hospital exec role to start his own consulting firm, which became a thriving, purpose-driven company. But even with all of the success, something didn't sit right. After a bold exit and a reinvention, he's now an advisor and executive coach for purpose-driven

leaders, helping founders and CEOs navigate their toughest challenges with clarity and heart. Jonathan brings a rare blend of boardroom strategy and deep listening. Welcome, Jonathan. Hey, Adam. It's so great to be here. Thanks for having me on. I love this type of conversation where I get to talk to a leader, somebody who's done it, somebody who's founded companies, somebody who's exited companies, and somebody who's in the mix still. So let's kind of take a step back. You founded a company, you found success, and it seems like maybe that wasn't enough. So take us back to that point and tell us, why did you know you found out a company why did you leave it and where are you at today yeah thanks so um i spent 10 years building uh and scaling and management consulting company

um we served hundreds of clients across uh you know Canada which is where I'm located um we became a B Corp um and it was really successful at some point I just hit a moment where I realized I wasn't loving it in the same way anymore it wasn't that I wasn't delivering great work and that any particular project wasn't lighting me up. There was just something about it that felt like it was starting to get less, you know, real for me or something. So I remember the specific moment when I realized I needed to make a change. I was on a trip with my wife in Dublin, Ireland, and we were walking down the street. And you know, when you're on vacation, you kind of have sort of the freedom to, you know,

as kind of immunity from your regular life. And you start sort of talking, you know, big picture. And so I was. I was talking with Wendy. And I said, you know, I think I might be getting kind of close to the end. And she said, you probably need a plan because you can't just give two weeks notice, you know. Like, you're, you know. So I realized right in that moment that I actually did need a secession plan.

And also that there was really. only one person in my mind that was ready to do the job who worked for me. And so she wasn't quite ready and I wasn't quite ready. So it was perfect. We jumped in together. We made a CEO transition and we spent the next year allowing her to run the company before ultimately she, you know, we did a management buyer before she bought the company from me. So it was a kind of like it all came from a single moment of realization, but the, you know, implementation took a good long while after that. These days, I work a foreign by myself. I'm like an executive advisor and I do coaching work and an independent board director, that kind of thing. Awesome. It's interesting because

I meet so many leaders that you just don't want to lead a company, but you're kind of a fulfillment seeker personally. You know, you're looking for that point where you go, okay, all right, done that, check the box. Time to move on to something else. But I wanted to touch base on the succession planning piece, because both you and I probably see this quite a bit in different organizations. It seems like it's a big gap in most organizations when it comes to, all right, if the CEO does leave, who's next? I mean, how often are you dealing with that when it comes to different organizations? Well, I mean, secession planning is the thing about which nobody wants to speak. And, you know, what I like to say around board tables, especially when I'm doing

consulting work around board tables, is like denial isn't a strategy here. folks. Like, let's, you know, there's a hundred percent chance that your CEO is going to leave at some point. We know that. So given the statistically probability here, what's the plan? And I think starting by normalizing the conversation, which is, of course, tied into performance management and the structuring of, you know, what success looks like from your key leader. But normalizing the, how are you? How's the conversation? Each year, make sure that we understand where their career is at. If they're, like, starting to signal that, you know, the end could be in sight,

then you want a formal plan. You want to know that their salary has appropriately been benchmarked, so you don't have to come up with a lot more dough embarrassingly at the last minute because the market has moved on from, you know, where you set the amount at. that we can look internally for candidates and what that candidate pool is like. And what, if any, professional development, do those potential folks need all the way to, are we going to use a search firm? Do we know what a candidate profile would look like?

Like normalizing that doesn't mean the person's leaving. Doesn't mean they're giving notice. Doesn't mean that they're not trying hard. It does mean, though, that you're mitigating risk and that you're having open and honest conversations about somebody's whose career and success you care about a lot, but it directly influences you as a board of directors. And so I think you cascade that down as well. So whether it's the next level down or the level after that, you know, managing folks with an open mind to the fact that not everybody stays forever, people move on and allowing them to build their skills and get good

enough to be able to take the next big opportunity, whether it's with you or with somebody else, is simply the right thing to do and normalize that conversation. That's a great point. I love what you said. There's a 100% chance that this leader will leave. It's going to happen. Come on, folks. It was funny.

I had a conversation with a large organization, about 600 people in this company. Maybe it's medium size. I don't know. But I looked around the room. I was talking to management and above. So anybody who supervised anybody else. And I said, what's the number one job of a leader? and they're looking to me, you know, to lead?

I go, no, it's to replace yourself. So it was fascinating when we started unpacking that because it took an uncomfortable situation of you're going to leave and turned it into you have a responsibility as a leader to train people around you to take your job. So I thought that was fascinating. So how did you introduce that to your replacement when you left your company and, you know,

was this a shocking conversation? or how did it go? Or was it kind of expected based upon your expertise? Oh, yeah. I mean, I'm not sure at the start that she thought had thought a ton about it. I just saw somebody who had the core competencies to be able to do the work. And I could see how much delight she provided for our very best clients and how much respect she had internally.

And I don't know whether it's a little hidden talent of mine, but like I'm really, really good at spotting CEOs early in their career before they know that they're going to be a CEO? I'm just, I don't know, I'm good at it. And I just saw in her, like, people that can make quick and fast decisions, people that are really good at integrating lots of broad ideas and then bringing it to a head. People are good at the driving forward. People that can see what's after what's next. These are the kind of attributes that they don't, you know, you don't, like you learn a lot of those things over the course of your career, you get more confident, you build skills and competencies and all that sort of stuff. But not everybody gets to the point of being the kind

of person with a personality that can do all of those things. And I like to spot them. And so I had spotted that in her for sure. And so it also typically is the kind of person for whom that is the deep secret deep down. They're kind of like wanting that, you know. So if you can pull it out early, then they're like, oh, yeah. And I think she was ready. for that. And she frankly had led things before. So this wasn't the very first time that she had been a leader of an organization. That's for sure. So yeah, that was really what was going on. And I just, I delight in finding people early in that in that sort of leadership trajectory and saying to folks like, you will be a CEO one day. You will remember this. And I bet you. I'll take that

bet right now. I love that. And obviously it just doesn't happen. It's not like just pushing a button in an elevator and expecting to get there. You know, it takes a lot of hunger and humility and that personal drive that they have to have. It's, it's unfortunate. A lot of times I see, you know, boards of directors, you know, the nominating governance committees, things like that on the boards. They call a list of a few people a succession plan instead of a full development profile for those people to help them understand, you know, how to get to the role. But I want to change channels a little bit on this and talk about, you know, we find leaders and we have our eye on them for their development. But sometimes leaders get stuck. Do you, do you ever see that happen,

you know, in their personal growth? Maybe they start to exhibit signs of burnout or something like that and they need a little bit of enhancement or, you know, inspiration in order to get moving again to become something more. Talk to me a little bit about that. Yeah, that's inbound where, you know, a good number of folks come my way with that. You know, they've tapped out at the C-suite or the layer below the C-suite and they're thinking, like, it can often be like ages and stages in life as well. Like when you've got young kids and young families and you've got it all going on, the drive that you had prior to that can not be with you for a while. And, you know, so kind of coming out at holistically, I think is really important to take

in the full picture. For some folks, they just, they genuinely do get stuck, right? They get, they get stuck in fear can hold them back. Sometimes it's fear of success, but sometimes fear of failure. Sometimes it's just they've never imagined for themselves what moving up or out might look like. And so one of the things I like to do is just. go on an imaginative journey with my clients, especially if they're feeling stuck and

or they feel like they've exhausted this part of their career. So I worked with, for example, a senior communications person recently. And we just, she was like, I just, I think I'm kind of done. Like I, I, like, I've got all the skills and I've run big, huge comms departments. And like, I just, and I know I, I'm ready for the next thing, but I just don't think it's the exact same thing but somewhere else. So we kind of played a game. Like I just made imaginary character sketches of her in a year's time in a whole series of different jobs.

And so I like pretended, I'm like, you know, like on the Google map where you like dangle the guy and he's like, they're dangling. I'm like, I'm dropping you in this job in the future. And I'm going to just describe to you what your Tuesday looks like in granularity. Like what your back-to-back meetings, what your stakeholders, what your folks and your clients and your customers, like what they are wanting and what you're doing and all that. And I threw her in a bunch of different scenarios, it's like all the way from running a non-profit to running a foundation, to going out on her own as a consultant, to moving inside

a huge institution that's an educational institution, which was totally different, to moving inside of healthcare in a project management role. Like, I just like tried to get her to just get out of her head and just like, and she had physical responses to each of the scenario. eyes. And I made her sit with them. I'm like, how's that feel? And she was like, awful. Like, oh, I couldn't imagine anything worse. I'm like, great. We just narrowed everything down. Right. It was great. And I'm like, tell me more about why that's not good for you. Oh, I would hate this. And I would hate that or anything. And then some of them were like,

oh, like, I've never considered like what that would be. Like, how would I be with that? There was a lot of curiosity there and everything in between. And it was from that that she was able to kind of narrow down personal search and be able to kind of create that narrative around the transition and she started interviewing and ultimately got a new position in a completely like an adjacent field but in a new way. And that, you know, was a part of, she also did a lot of personal work and other stuff, but like it was a part of her journey, which I think was really helpful because it broke her rigid thinking. Do you think they're really, I don't want to say aggressive leaders, but the the really profound leaders that that really work hard at it at running their businesses

sometimes take for granted where they're at in their business. And they just, you know, that, that wandering mindset starts going or the fact that they have nobody to talk to about appreciation for the success that they've created and motivation for the future. I mean, it just, I guess what I'm trying to ask is, you know, we feel stuck someplace, but there might be a beautiful. place that we're stuck in and we just don't realize it. Do you ever see that? Oh, that's lovely. Yeah, that that's beautiful. It's sort of the complete opposite of all the things that I was just saying and I love it. Yeah, like actually taking time to step back and consider what you've built

and who you've become and how you're showing up in the world, that that gratitude and expression of that is a beautiful thing. And I think that sometimes we move so quickly. And frankly, like, things, especially if you're a founder and you're running and owning a company, it's really isolating. It's really, it can be lonely in its worst moments. There's only so much you can tell your board or your investors. There's only so much you want to tell your staff without freaking him out. There's only so much you can bring home to your poor spouse, you know, without boring him or her to tears. So what do you do with it? Well, you just bottle it up. You suck it up. You're the boss. You're the leader, right? Like, you know, and at some point, though, it leaks out.

It's like squishing the old balloon. You know, at some point, it's going to burst out. And maybe you become short-tempered. Maybe you, you know, over-commit and just whatever. And so that can ultimately result in getting, as you say, stuck. And how do we pick up the needle and move it back onto a thread where you can find the gratitude and the joy again of this incredible thing that admittedly you built? Yeah, incredible.

Hey, I want to dive into something that you talk a lot. lot about that leaders struggle with and that is deep listening and it seems like you know what we're doing is talking about deep listening from a leader but take me through what is your definition of deep listening and how can leaders a benefit from this so keeping the horses in the barn in a conversation is a skill and you can build it deep listening is more than just sitting in a conversation listening enough that it sparks and oh yeah i know a thing that's like that and i then wait and i polish the thing in my head the story the anecdote until you stop talking i'm not really listening to you i'm actually just polishing the thing in my head and then when it's

my turn i buddy in and i just say my thing and the start of it does the same thing to you and you stop listening to me because you're polishing the next thing. Oh, yeah, that's just like a thing that happened to my brother-in-law. Oh, really? Yeah. Oh, my God. That's the thing that, like, you know, and then we do that all the time. And we're not absorbing a lot from each other.

Why does therapy work? Why does really, really good coaching work? And why do you have to pay for it? Why can't we just do that for each other? Because these are actually really defined skills that people are using when they're sitting with us. And so if you're a leader, and this is like, you know, I share this with everybody, but like if you learn the skill of mirroring back to people, validating and mirroring, and you practice that in a really intentional way,

you will completely transform the kind of leader you are, which sounds something like, Adam, thanks for that question. That sounds really hard that you're going through. Huh. Can you just tell me a little more? Okay. Listen, before I jump in here, I think what I just want to, I just want to make sure I'm tracking. I think first you said that it was really hard with the thing and then she said this and then after that you responded with this and you tried this but it didn't seem to work and then she did this and then you did that. Now have I have I got that? If I do that to you, you will feel so seen and so deeply heard, it won't actually matter whether or not I solve your problem. Now hopefully I can. But if you do that,

the person will feel so seen it's and sadly it's very rare in life but we've all got a friend or two that just for whatever natural reason happens to be really pretty good at it and why we all show up at therapists and coaches and stuff is because we actually need it like we crave this sense of being really seen and really heard and that's what we're looking for when we do that so if you're the kind of leader that wants to just learn more about how to infuse coaching or infuse some deep listening into your leadership practice. Just start by training yourself on how to do some validation and some mirroring back. Those two skills alone will take you to the next level. Amazing. Amazing. It's it's so empowering to everybody at the table, it seems like,

when you have a leader who gives them the ability to open up and actually share what's going You can use these skills one-on-one, but you can also use them when you're facilitating meetings, right? Like, there's nothing more beautiful than being in a meeting when somebody is chairing that has those sorts of skills. They allow everybody to equally participate. They shut down somebody that's being a blowhard. They make sure that we're summarizing, that we're all hearing what one another is actually saying. Like, they're connecting and being integrative. Hey, Adam, your idea is similar to what I heard Sally say.

earlier, would anybody else like to build on that? Does that feel like we're ready to action that? Like that kind of pulling together, as opposed to what most chairs do, which is use it as a bully pulpit and to speak too much and to use it as a piece of power dynamic. Instead, the opposite can be true. You're holding the container and you're supporting everybody to participate and to feel seen and heard. And meetings like that are wonderful. Like there's just, meetings have got a bad rap it's not meetings that destroy like what is a meeting a bunch of people sitting around a table like there's nothing wrong with that it's the hell that's wrong and that's why people hate meetings is because they're badly wrong totally it's i mean we could we could spend hours on

this i'm sure watching the leader from the bully pulpit not let anybody speak and just throwing their ideas at them it's it's incredible all right let's let's talk about this um fulfillment finding type situation with leaders. I mean, it's a great thing for organizations and leaders when leaders are hungry, like very hungry to do more and become more. But how do we as leaders recognize that we're starting to wander instead of focus on, you know, really proper development in our organization, a proper focus on our organization and kind of re-center ourselves so that were most effective. Yeah, that's a great question. I think that if your practice as a leader has been to interrogate your own, the stories that you're telling yourself about what you're

doing, that it's from that place that you can catch yourself early. We all wander and drift. We all do. It's normal. But a lot of people are relying on you to be good at what you're doing. and if you've come to your natural end, get off the stage while the crowd is still clapping. Don't wait until you're driving into the ground. There's nothing left. Whether it's a sale or whether it's just retiring or whether it's my time, I'm going to step back or I'm going to, I need to resign or whatever it is. Like do it in a dignified cool way, but don't do it until, like don't wait until you've got literally nothing left. You're also never great if you're going on the job market.

and you're completely spent and exhausted and you fell over the line, like, that's the worst place to be a good candidate from. So while there's still some strength, you want to think about that. But like south of that is just the normal drifting, the normal things. And we start to tell ourselves stories and make up excuses. And they're convenient and they're settling, but I think we should be suspicious of them because they tend to be rationalized. of why things aren't maybe going the way they could be going and it's what's happening there.

Oh, we're not making the right decisions. We're not letting that person go. We're not making a bold new move. We're putting off deploying the thing. You know, we're spinning our wheels in other ways. Yeah, sure, there's lots of great reasons. But the truth is, whatever the truth is. And, you know, I probably like yourself, Adam, people hire me to help them make decisions. People hire me because they want on some level to just cut through the bullshit and actually own up to it and hear it and say, oh, I've just got to do it. I'm like, you really do. So how do we bust through it? How do we just make the choices and how do we make the decisions and how do we light it up? And that's part of the, you know, I love the work I do. It's very intimate. And it's quite powerful because I get to be with

people in those moments where they're like, oh my God, you know, without quoting Taylor, it's me. on the problem, right? I need to get through this and I need to do it. So it's really quite, it's really quite wonderful for me to be supportive through, through those moments and help people. Awesome. Come to the decisions that they need to. So good. I'm always looking for that little tidbit of leadership advice and insight that can help me take another step up on the staircase of life and lead better and have a little more humility and continue to grow the leaders under me. You know, we talked about succession planning. So if you're looking for Jonathan, you can find Jonathan Bennett online at clearly then.com.

Make sure you check out Jonathan. He's got a lot of great information on there. And also you can hire him if you need to focus on your leadership. And frankly, we all need to have somebody helping us grow our leadership. So definitely reach out to Jonathan. He's helped hundreds of clients, a lot of major organizations, a lot of board directors, and Jonathan also sits on different boards of organizations to help with that. So Jonathan, I have a question I ask all of our great leaders on this show.

And we all have a routine. And I'd love to hear yours. So how do you start your day with a win? I start my day in the same way that I advise my clients to start their day, which is not on email. I start my day in my calendar. And what I like to do is take five minutes and go through my entire day and imaginatively drop myself in each meeting and ask myself, who's in the meeting? What do they need? What do I need? What does success look like? And I do that at the start of my day. So I've thought of my whole day, largely because I'm trying to manage my focus and my energy through

the day. And if I see that I've got something really big at three, that I need more time to prep for, then maybe my thing at 11 could be moved. And so that's what I do. And that's how I start with a win, which is really like a focus on my, how I'm going to show up. And I do that in a really practical way, which is like I use my calendar to make myself do it every day. I love that. That's, that's amazing. It's, it's very similar to how I do it. I'll, I'll take a look at the week on Sunday so that I can manage it from a 30,000 foot perspective. And then each morning, I'll sit down and I'll take look at it and I'll go, okay, what time am I eating? What time are my hard meetings? What time are my easy meetings? Energy management is a real thing, people. And when you are a leader and you show up,

you better have the energy in the right places. So Jonathan, that's some great advice. Awesome. We really appreciate all that you do. This has been some incredible, incredible information today on how leaders can move the ball forward, how to continue to rejuvenate, how to start again when you've taken and kind of hit that wall of fulfillment and need to continue moving on. And also, of course, I said it again, succession planning. It's important people. Work on it. So make sure you check out Jonathan Bennett online.

And Jonathan, thank you so much for all you do. And thanks for being on Start with a Win. Thanks so much, I'm just great to be here. Thank you.