Ben Levitan – Room For Learning at the Highest Levels | Conversations with Coaches | Boxer Media

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Ben Levitan - Room For Learning at the Highest Levels | Conversations with Coaches | Boxer Media

Ben is a C-Suite Executive, Advisor, Independent Board Member, and Investor with a broad range of experience in public and private companies. Ben served as a CEO at four technology companies and has been a dedicated CEO Coach since 2014.

Ben founded Cedalion Partners to help leaders and investors improve and grow their businesses. He has served clients in the technology, software, business services, cybersecurity, and communications sectors.

In today’s episode, we talk about the importance of coaching for people at the highest levels of leadership and in the C-suite, as well as the unique and powerful opportunities for learning that a good coach can provide and make room for.

To learn more about Ben:

https://cedalionpartners.com/

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Kevin Stafford 0:02
Hello, everyone, and welcome to another episode of the conversations with Coach’s podcast. I’m your host, Kevin. And today I have the pleasure of hosting Ben LeBreton. Then is a C suite executive advisor, independent board member and investor with a broad range of experience in public and private companies. Ben served as a CEO at four different technology companies and has been a dedicated CEO coach since 2014. Ben, I’m excited to talk to you today. I know we had a we had a ships passing in the night you were actually on a meeting with a client and you reached out to me what while you were in the meeting and said I’m running a little bit late, and I was so glad that you reached out and I just wanted to immediate like rush in and be like clients first clients first take as long as you need. So I’m glad we were finally able to connect.

Ben Levitan 0:44
Yeah, that’s all about clients first problem.

Kevin Stafford 0:47
So let’s, uh, let’s, let’s reach back a little bit into the past here. And I kind of like to ask this question cheekily about what your superhero origin story is, I like I like hearing about how a coach that just got their start, but kind of realized or discovered, or were told by a key person a key moment, that coaching or gave them the word coach and kind of unlocked what that might mean for them personally and professionally. So what were your What was your start? What was your realization moment as a coach becoming a coach? And then how did that develop into the coaching business you have today?

Ben Levitan 1:18
That’s a terrific question. My, my career in technology took me to some great places. And one of them was a company called Cambridge technology partners back in the mid 90s. And I had the good fortune to be an executive there and was recruited away to another company, having gotten the benefit of that business system that Cambridge had, I was early there, and had great, great success. They’re being coached and mentored, if you will, by by a boss named Robert jet. But I joined James Martin and quickly thereafter realized that I didn’t want to be doing what I was doing. So I went to the board. And I said, I’d like to part company now and resign, and they said, Oh, no, no, no, no, no, we’re gonna make you the CEO. And I was flattered, but unconvinced and I said, Well, I kind of feel pretty good about the job of it. Now, I’m not sure I’m ready to be a CEO. And they said, don’t worry, we’re gonna get you a coach. And the vice chairman of the company, a fella named David Fairbairn, for all of you who like Guinness beer, he’s the one who brought Guinness beer to the US, spent a few years coaching me on how to become a CEO. So that was the first time that I had a dedicated coach, and dedicated mentor, I would say, who spent a lot of time with me, both in person and in meetings. And it helped me learn, and frankly, refine my leadership style and my management style to be successful. That set of tools that he taught me those set of insights that he gave me about me, and about the situations that either activate me, or affect my effectiveness, affect my effectiveness and networks revealed for me, and from that point on, I was a C suite executive. And then, shortly after I concluded that experience, being a CEO, I got hit by a car riding my bicycle, which significantly changed my life. As you can imagine, fortunately, I had great care at Spaulding rehab here in Boston and decided that at that point that I wanted to do coaching full time I wanted to be a resource the way I had been a Reese been given a resource as the CEO many years before, so that I would say is my, my origin story as a coach, but I can say, confidently, it probably started a lot earlier, since I’m the youngest of four children. And I had older siblings who taught me an awful lot, both by their actions, and by their advice, let’s call it when you’re in a position to be given those kinds of opportunities. You can accept them or not. And for me, I thought they were mostly a present except for my brother would roughhouse with me of course. But that was those are probably the two elements both the good fortune I had in my family, with a professor and a school teacher for a mother who you know, learn Burning curiosity were very important. And then having the distinct experience of feeling overwhelmed as a CEO and getting someone to help me process and improve in ways that at times are quite easy at times are quite difficult. So that’s my origin story. Love that.

Kevin Stafford 5:25
I first of all, I love the fact that your parents were were in education, that’s that’s unsurprising given given the way that you communicate in the way that you and what you do. And it’s actually has me thinking, again, doubly so about something that I was reminded of as you begin to tell your your sort of origin story and that how we spend such a tremendous amount of our early years in engaged in formal or informal education, for obvious and very good powerful reasons. And then we reach a point, for some people, it different points for different people, depending on how their life goes. But we reach a point where that just kind of stops, and you just are sort of like cut loose into the world. And you’re meant to just kind of like learn what you need to learn from wherever to get it wherever you can find it, and go forward. And it’s one thing that I’ve like, I’ve come to think about certain kinds of coaching as sort of a continuing education. I know that continuing ed sort of has like a different sort of connotation, but it’s there’s a huge gap in where people can go, where they’ve already left their quote, unquote, official formal education, but still have things that they want to learn in a structured way, they need people who to teach them to show them to equip them with the tools that they need, and the skills that they have to have and develop, to go where they want to continue to go. And I feel like coaching steps right into that gap by offering not just more of the same, it’s a more sort of interactive, obviously, one to one is where the real action happens. But they’re even in like larger scale, even if it’s just like a keynote speech, or you have like a group mastermind, which is just another way of you know, saying you have like a high level college class, you just look at the form that education takes, and I like, like this two week aboard, I genuinely love the way good coaching steps into a an education gap, and fills it in with the kind of education that people are really, really hungry for as they move through their lives.

Ben Levitan 7:18
Well, you know, with coaching, it’s quite interesting. Sometimes I’m engaged with folks who aren’t immediately open to the idea of coaching and they’ve been informed or or led to the conclusion that if they were to close some gaps, which often happens, they would then get a promotion, they would then move forward in an organization and it would have a whole positive effect in their professional outcome. And that distinction between I’m going as the saying goes from good to great is a gap that is logarithmically harder as you are an adult, right to your point, adult learning is a different kind of a learning, often more applied. And so one of the first things I like to think about when I’m meeting somebody or been asked to meet with somebody about their growth, is to figure out what their goals are. Sometimes the goal is to learn how to learn, I have been busy. So so overwhelmed by doing and doing and doing, I really haven’t had time to step back and learn. And often I hear about goals that are not necessarily what I would call classic business goals. You know, grow the team X amount, or learn how to do a public presentation or you know how to present to the board, whatever it may be, it’s often includes a goal about sharpening the blade learning how to learn. And that that’s very exciting for me when people have that self awareness. But as I said, some folks don’t. And so it’s important to build that trust, that it’s okay to fail, that learning is is not pass fail. And certainly learning how to be a more effective leader is a process, not an event. And that that dynamic is something I certainly learned over the couple of years I was taught how to be an executive and learned how to be an executive, which was, you know, obviously the culmination of a lot of other positive experiences and developmental experiences I had, but the dedication to a goal that is what I’ll call below the line, not exactly visible in the coaching the typical coaching objectives makes a real difference to the velocity that somebody can pick up as they practice tool. pools and bring back results and learnings.

Kevin Stafford 10:04
That’s another another aspect that I feel like especially for high level leaders and CEOs. There’s often a lot riding on your performance and your abilities, sometimes perceived, sometimes perceived only in one’s own mind. But often you carry a pretty heavy burden. And there can be a lot of stress and pressure there, that pushes out your willingness to, to, to fail in any perceivable way, because you feel a certain kind of way about the way you need to perform, or you have certain responsibilities. It’s a little bit of a high wire act, sometimes, especially for the highest level leaders. And one thing, and this is something that only gets talked about enough is what a coach can bring to a high level leader to a CEO in terms of room to contemplate things room to fail a little bit, in an inconsequential way, to the company to the team, to the people that they serve as CEO as leader, that allows them to learn how to succeed where in when it matters most with the most impact and the most positive effect. And I don’t think it gets talked about enough how that that space that coach provides for especially those high level leaders, to step off the high wire, and actually learn how to walk that high wire even better, with greater balance in a way that serves everybody. It’s something that I love thinking about that because it’s so rare for someone at that stage in their development, to find someone to help them find that space.

Ben Levitan 11:27
I think you make a very good point. And I find it in my practice, where I’m often coaching high performers, who are growing into a new role first time CEO, or maybe second time CEO, but in a different industry with a different ownership or shareholder dynamic. And declaring that there’s a learning gap is quite risky. Because you, you take the traditional expectations of the CEO, you’re expected to do what is expected to do everything they used to know how to do with ease. But they have to work through other people in a way that is quite complicated. And the biggest message I often give to people is you are not the CEO, you are the current executive officer, you are part of a story that has gone on in the company, from the investors, to the board members, to your senior managers about what came before where you fit, and where things are going. And so being very cognizant of the context, within which you’re being asked to do different things, is extremely important. And one of the big skills for a CEO is context switching. Be very aware of the difference between what I’ll call the ceremonial or performative part of the job, versus the hard decision making priority setting and balancing those out in such a way that the people who work with you understand that you’re practicing as you are performing some of those things, you might be more naturally inclined to be analytical and introverted. Uncomfortable in a public setting. You may you may be much more comfortable alone and contemplative. And that the CEOs expectations of themselves need to be reconciled with what the expectations are based on the context of the activities that are involved in

Kevin Stafford 13:42
that see and CEO can mean a lot more than just chief can it? Absolutely. I have so many like in my in my head like obviously this is this rich material in my head, I have like a half a dozen different like off ramps to tie in like conversations that could go for hours. I feel like this is one thing or two parts, two parts. One thing I love how much more we’re talking about this kind of skill acquisition and learning because a lot of times it’s there’s there’s a sort of a command and control element to leadership, especially at the higher levels where it’s, you’re meant to step in and sort of like a black box, you just kind of figure it out. You do it. It’s what’s done. You read somebody’s book about how they did it. And that’s supposed to be the education that you get, like you just learn how you know, you know, the CEO of GM or the you know, whatever’s going on in Silicon Valley, like you learn from them, and you kind of figure it out, you’re supposed to just figure it out as white knuckle your way through. And I just, I really, I I can’t express how much I appreciate the fact that more people across industries at every level are not only willing to talk about what it takes to learn and grow as a leader in the context of not just your organization, but just personally in your life and your family everywhere. Not just talk about it, but actually engage with it. It demonstrates a kind of vulnerability that I feel like is The beginning of a flip of what vulnerability means for some people, because vulnerability is a little bit of a dirty word,

Ben Levitan 15:05
it takes a lot of courage, it does. Because the successes are often accrued to the people who work with you and around you and the failures accrue to you at the top. One of the things back to your earlier comment about CEOs getting the space to think things through one of the principles I operate on, is called constructive conflict. So there are some CEO coaches whose practice is very much oriented towards like mine is towards goals and how you’re going to achieve goals and reporting back and acquiring skills on how you’re going to get them. But they often bristle at the idea of being challenged, and that their fundamental assumptions are being challenged. And what is very clear in the CEO role, which is different than many other roles is that your fundamental assumptions, get constantly stressed, by the decisions that you make, you want to go east and the organization says we’re kind of Northeast, the market says you need to be moving west, and you’re busy trying to describe to people things that they don’t know or see that only you understand because of your access to information. And your engagement with the market and with the employees is very different than anybody else’s. So there’s often a dynamic where the CEO has to learn how to question their own assumptions, have them challenge, but at the same time, bring people along to the emerging rowing organizational needs. And it’s not entirely clear. So I often say the heart of being a CEO is making a decision before you know what the right answer is. And when you do that, you end up six, if you do it successfully, you end up sharing with folks, what are the assumptions that are guiding your decision? What are the blind spots you’re still testing for? And really, how far is your conviction into a particular direction many books, as you point out, simplify the role of the CEO. But I can say with confidence, having worked with many over these last few decades, they know an awful lot, but they succeed when they realize how little they know, and how curious they need to be to stress their own assumptions, let’s call them

Kevin Stafford 17:38
yeah, that, that that marriage of curiosity into the unknown, and an ability to make decisions and take action, the combination of those things that’s, that is I think, that’s why CEOs are so rare. And so special, good CEOs are so rare and so special, less so as we go though, because I feel like we’re understanding more what it takes to hold to understand what you know, to hold the uncertainty of what you don’t know, in inside your mind. And not or, and to be able to make decisions and take action, individually and collectively, to lead people in those decisions in those actions. That takes a strange alchemy, a mix that might

Ben Levitan 18:22
take away some folks approach it much more analytically, because they’re naturally introverted. Maybe they’re engineers, or more analytical, or scientists, others are constantly let’s call it extroverted and are always running for mayor, right? They’re always doing things. In both cases, communication is very important needs to be constant. But the fact is, is each person communicates in a different way. So sometimes I’ve worked with folks to understand what is their user manual? What is it that if you were to meet somebody and you were to hire somebody, what would they need to know about the way you make decisions, process information, communicate and persuade. And many times that is a quite a breakthrough exercise because you force them to go deep on to what they believe and what people need to know about them in order to be a good colleague.

Kevin Stafford 19:22
In my head, I’m sorry, I was, I was just gonna say an analogy that just popped into my head and I wanted to, I wanted to test it with you is that a lot of times when we’re when we’re beginning a relationship with someone, especially professionally, but across all walks of life, we’re giving them the quickstart guide. Like you just got like a new computer or some like large complex appliance, you give them the quickstart guide. It’s just this is what you need to know to get us going. But there’s that much thicker manual that has like details about like, Okay, this is the details about how the operation of this device is how how this actually works, and I like the fact I like the ability to both deliver a quickstart guide to be able to provide people with what they need to know About me, my strengths, my weaknesses, my vulnerabilities, my availabilities, my communication style, who I am, give them that quickstart guide so they can get to a good plug in relationship with me as fast as possible. And I’m in and I’ll constantly be writing these guides in this analogy, I also want to have that like the user manual, where it’s just like, this is more about the language I speak and the way that I think and the way that I make decisions. And I want you to know this too, and I want yours if you have one. So that we can just get in this is where the analogy begins to strain so that we can get on the same page, but more accurately, speak something closer to the same language.

Ben Levitan 20:36
So your word, your use of words, I think, is quite powerful here, Kevin, because the words we use and the power words that mean more to you, and maybe then to other people are extremely important to identify. So even that user manual is going to have loaded words in it. And it’s going to signal certain things to other people. And you almost need to decode what the words mean, for me, I like and in our practice, we like to add science and technology to that process. Some people say, well, let’s do a 360. And after you get the 360, I’ll know what you’re, I think it’s extremely important. And I use a tool called Predictive index. Other people have other tools. And I use other tools as well, that give us all shared language in a very simple way about what what I’m like. So for me, for example, I’m a maverick, which means a bunch of important things. But mostly, perhaps the most noteworthy trait is among afraid of failure. So I work best with clients who like to experiment, like a hypothesis, and then they’re gonna run a sprint, and then they’re gonna evaluate what came back, rather than describing them in a fixed way. And then running a play to its end. So we’re going to try and run a better planning process. Well, that’s great. But there are different ways to run that assuming different. Let’s call it tactics, you can use different tactics to get to the same goal. And trying them out is part of the power of what you can do with a coach. You can you can roleplay you can rehearse. And you can then report back on what happened. But it all starts with a baseline understanding of who am I and who are you? And what are we trying to do together. That’s that that context and that trust that you built there. And the goal that we agree on, makes for very powerful medicine, very powerful medicine.

Kevin Stafford 22:53
I couldn’t agree more. And I’m my eyes dart up to the to the clock in the zoom window, and I realized we’ve already been talking for nearly a half an hour. unsurprised but always, always pleasantly, so that this conversation has gotten some excellent directions, I would love to have you back on for part two, I would love to just keep you all day. But I know that we will have things going on clients to serve and people to help. But before I let you go today, and then sneakily invite you back on for part two, somewhere down the road. let the audience know, please, where it’s kind of a two part question where people can find out more about you what you do, what your company does, how you serve, the various offerings you have, and then also where people can best connect with you if they want to start a conversation or start a relationship with you.

Ben Levitan 23:36
Sure. So my practice is called medallion partners. Cee d a l i, o n partners, you can contact me at medallion partners.com, Bennett’s medallion partners.com. Or connect at stallion partners.com. I have a group of colleagues as well. It’s in Sudan talent, which is part of our practice. And you can reach me and reach them at Sudan talent.com as well. I do tend to avoid cold outreaches on LinkedIn, because I find it to be a bit overwhelming. So I do like to have as much context as possible, delighted to speak to your audience. And frankly, I’m flattered you would ask that, that I’d return so thank you, Kevin.

Kevin Stafford 24:22
Yeah. And I’m, I just I’ve enjoyed this conversation so much. And like, I feel like I spent almost like a Velcro ripping away a little bit because this is like there’s so much meat on the bones of everything that we’ve touched on already. I feel like we’ve just scratched the surface. So yeah, I will definitely be sneaking into your LinkedIn DMS probably in the not too distant future. Next month, so thank you

Ben Levitan 24:44
so much for funding to be a coach. It’s it. There’s so much there. I get very excited about the potential to increase human performance. Like other people have invested in me and I’m delighted to pass along the other. So thanks again for inviting me.

Kevin Stafford 25:04
It’s, I can genuinely say it was my pleasure. And I look forward to it again. And to the audience. I mean, just you’re listening to this, you can tell, you can tell what Ben what Ben’s made of reach out, find out more connect, learn, see if there’s a good fit there. And you might be in a position where what Ben has to offer what Ben and his partners have to offer is exactly what you’re looking for exactly what you need. So yeah, don’t be afraid to reach out and I will have him back on again. But you can listen to that episode, whether there’s, in the meantime, we will talk to you again very soon.

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