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Business is an unlikely hero: a force for good working to solve society's most pressing challenges, while boosting bottom line. This is social purpose at work. And it's a dynamic journey. Purpose 360 is a masterclass in unlocking the power of social purpose to ignite business and social impact. Host Carol Cone brings decades of social impact expertise and a 360-degree view of integrating social purpose into an organization into unfiltered conversations that illuminate today's big challenges and bigger ideas.
Carol Cone:
I'm Carol Cone, and welcome to Purpose 360, the podcast that unlocks the power of purpose to ignite business and social impact.
Each week we uncover how purpose can transform organizations, inspire leaders, and help people flourish. Today we're diving into a topic that sits at the very heart of purpose, leadership. Joining me is an old friend and an incredible thought leader, Scott Osmon, CEO of 100 Coaches, cited as the world's most renowned leadership coaching organization. It was founded by legendary Coach Marshall Goldsmith, and in its work, 100 Coaches has guided many of today's most influential executives, helping them to lead with greater authenticity, clarity, vision, and heart. In our conversation we'll explore what does great leadership look like in today's world, how leaders can balance empathy and vulnerability with accountability and performance, and why purpose isn't just a nice to have, but a strategic imperative.
As Scott reminds us in this conversation, leaders are stewards of their companies, their people, their customers, and their ability to impact the world. So get ready for a thought-provoking conversation on the next frontier of leadership, one grounded in generosity, humility, and purpose.So welcome to the show, Scott.
Scott Osman:
Great to be with you, Carol.
Carol Cone:
Oh, it's just great to see you again, and it's every now and then we catch up and I'm always learning something great from you. So I want to start, I always love about asking our guests what were their early in your life influencers that led you to your philosophy today and the kind of work that you do?
Scott Osman:
It's a great question. My grandfather was one of my early influences. My grandfather had a men's clothing store in Stanford, Connecticut where I grew up, and I used to hang out at that store and I watched him interact with customers and I heard the stories that they had. And people would come into the store one way and he would fit them with a suit and they left feeling so much better.
Carol Cone:
What a wonderful influence. And so what did you do? Did you hang out in his store as a young person? And what'd you do there?
Scott Osman:
I used to hang out and chat with the customers, chat with the tailors. We talked philosophy, we talked about clothing. We talked about why clothing made such a big impact on how somebody felt about themselves and how they're perceived by others. And it really was an instrument. I think it was his instrument for elevating other people. And I think he really felt that very, very deeply.
Carol Cone:
What inspired your transition to leadership coaching?
Scott Osman:
I was doing some consulting work. It turned out to Tuck School to Dartmouth and my counterparty there and I were having in New York and he asked if he could invite this guy Marshall Goldsmith to dinner. I did not know Marshall at the time. I looked him up on Wikipedia. I thought, oh, this guy will be interesting. And we had a great dinner. Marshall and I really hit it off and we stayed in contact. And then he called me up a year later and he said, I want to teach 15 people everything I know about coaching. It was his pay it forward initiative because Peter Drucker had been generous with him.
And I love an adventure and I love saying yes. And so I said yes. And he put up a video on LinkedIn. 18,000 people applied and it was quantity and quality. So it was a lot of people, but it was also some of the most incredible leaders and leadership thinkers and leadership coaches in the world wanted to be trained by Marshall. And so we ran the first session. I did something kind of intriguing when it was so much fun, we did it again and I invited people from the first session to the second session. And because of that interconnectedness created community and that became the 100 coaches community.
Carol Cone:
And so talk a little bit about the services that the 100 Coaches as a company provides. It's a really distinctive way that you are helping people advance to their fullest potential.
Scott Osman:
So we talk about at 100 Coaches the purpose of coaching is to create what we call human flourishing, what we all call flourishing, which is it's not just about helping leaders make more money for their company and shareholders. That's important. It's definitely important for them to have a better sense of their own balance, personal balance. They can't be effective for the company if they're eating themselves at work and also all the communities and stakeholders that they work with. That's what true leadership is.
True leadership has purpose at its core. The services that we provide 100 Coaches, the core service we have of course is matching the best executive coaches in the world with the leaders who have the most impact. We're firm believers that the people who really need coaching are people who are in what we call value hotspots, which is those roles within the company that are going to move the needle in the company. Not always the highest leaders, although they're very often the leaders that we're working with. Sometimes there are people further down in the organization that are in roles that are actually critical to the company and getting coaching for those people also very important. And then we just have a very particular way of doing it. We call it match craft.
Carol Cone:
Talk a little bit about that, because it is a fascinating process.
Scott Osman:
Yeah. So match craft is a very human interface to making sure that people get the right coach. All of our coaches are independent contractors, they're all solo entrepreneurs, they're different from each other. And trying to find the right coach for somebody if you don't know the coaches is very difficult. But since we're in community with them, we really have a deep understanding of each coach's particular way of coaching and their background and what they know about leadership. And so what we do is we have what we call a discovery call, the first call in the match craft process just to understand what the leader's looking for.
And we'll often spend a half hour either or more to understand what the issues that they're facing. We're listening not only for what they say but for what they don't say and the way they say it. We've done this hundreds of times now, so we're hearing things that they don't even know they're communicating. And at the end of that call, we're pretty good at saying here's what we think you're looking for in a coach. Did I hear you correctly? And we're right.
And then we take two or three days to think about who are the right coaches for this person? So we're now thinking, like you said, over 100 Coaches that we're drawing from. We reach out to three to five of those coaches. We find out if they're interested in the assignment, if they have capacity, willing to work at the budget. And then by the time we come back three days later for a curation call, we have three people that we think would be an extraordinary fit and not just great for this individual but different from each other. Because when you do a great curated set, you're actually helping people learn a little bit more about what coaching can do for them by giving them three different styles or approaches or backgrounds, whatever.
And if they agree with us, which they always do now, we then set up the chemistry calls. Because in order to find the right coach, you actually have to experience that coach. And it's critical to meet more than one coach. You know it's often the case, you'll meet one person who'll think this person's amazing, and then you meet the next person. You go, this person's also amazing, but for a different reason. And it's not until you've really met at least three people that what's really right for you. Not infrequently with us, I'll have a call selection call to find out who they chose and they'll say all three of them are amazing. I don't know how to choose between them. And we have a nice way of teasing out what they're really looking for. I personally think their difficulty isn't saying yes to one of them. It's saying no to two of them. It's awesome. Yeah.
Carol Cone:
Now you're been your coach, but you've also been coached, as affectionately called a coachee.
Scott Osman:
Correct.
Carol Cone:
That's really like you're in the shoes of your clients. I'm curious, what did you learn personally about having both sides of this equation and how does that influence 100 Coaches?
Scott Osman:
Yeah, there's a lot of things in coaching that are just like nobody. You don't learn in a business school. Nobody ever mentored you. They're just things that unlock what you need to know to run a business. There's another part of coaching that is having a neutral sounding board. I mean, especially when you're CEO of a company or a senior leader in a company, everybody kind of has an agenda and you don't have a very neutral relationship with anybody else in the company. And so having a coach gives you the opportunity to have that neutral relationship.
But I think my favorite part of coaching and certainly the most impactful for me was I found the coach who really I think did the most for me. I've had a couple coaches who've done this, is removing the internal barriers that we place on ourselves of self-limiting beliefs. In fact, my first self-limiting belief was things were good. The business was going well, I was pretty happy with the business, everything was going fine. And I was talking to my coach about that, and he says, "Thinking that things are fine as they are is a self-limiting belief because it's stopping you from expanding into the possibility and full potential of what you can do." And so that was a huge unlock for me.
Carol Cone:
That's tremendous. You also, one other trait about 100 Coaches is you talk a lot about generosity and why is that so important to the success of 100 Coaches? And it's just woven into so much of what you do?
Scott Osman:
Yeah, well, it goes back to that story I was telling of Marshall wanted to pay it forward. Peter Drucker had been generous with him and Marshall wanted, and that is really the absolute essence of our DNA. And candidly, I would say for most coaches, that's the core of coaching. I mean, certainly they should be well compensated. That's part of my job for the agency is to make sure they're very well compensated, but they're not doing it typically for the compensation, the job of a coach. It's such a high impact world, again, at the level that we're working at. So when you have the ability to work with a cadre, a number of different CEOs, C-suite leaders, even entrepreneurs and help them advance their company in a way, like I said, that creates flourishing, then you're having a pretty significant impact on the company and the society around that company. And that's all part of generosity.
Carol Cone:
I love it. Love it. How do you define leadership today? How do you define it? What are the greatest needs today in this chaotic world?
Scott Osman:
Leadership at its core is the ability to get people to follow you. So it's kind of a neutral idea. I'd love to say leadership is taking people to a higher place, but at its core, leadership is just getting people to follow you. If you can't get people to follow you, you're not a leader. And I have to say as you move up the ladder of leadership, so if you think about the way somebody progresses, they start a job, they're an individual contributor, then they get elevated to manager, they still know how to do the job, but they're telling other people how to do the job.
And then as you continue up, it just gets more and more focused on vision, priorities, inspiration, and then making sure everybody has the resources they need to be successful.
Carol Cone:
Yeah, absolutely. So when you've coached. What are different flavors of success that these leaders, they've been coached for a year or so, what's it look like?
Scott Osman:
Yeah, so there's a lot of different successes that happen in coaching. It's really good to establish what success looks like so that the coaching is coaching towards that successful outcome. Many other things will happen also, but we like to know this is what the company wants to see from coaching so that we make sure that we hit the mark on that. Some of the other things that happen from coaching that I think are wonderful successes is most leaders from coaching find greater balance in their life. Most leaders through coaching have a better sense of how they're perceived by others. It's one of the most consistent thing. I mean, I think very, I was going to say very few, almost nobody truly understands how they're perceived by others.
Carol Cone:
Because they're in a bubble in a way.
Scott Osman:
Yeah, I think I used to say the jam can't read the label on the jar.
Carol Cone:
That's very funny.
Scott Osman:
You can't see yourself from the outside because you're on the inside. And so a lot of what very often coaches start with a 360, and it's people around them telling people around the leader, telling the coach how they perceive that leader. And the coach distills it down and communicates it back in a way that the leader can hear, sometimes soft, sometimes hard. And the frequency with which the leader will say, oh, I'm sure everybody's going to say glowing things. And typically the coach will say, well, we'll see.
And it's always diverse, and you learn a lot. And that is, I mean, one of the biggest successes of coaching, I think can be a healthy dose of humility and recognizing that a lot of the things that you thought you were doing well, not so good, being a better communicator because you think you're communicating well. And then you find out, here's a big thing that a leader's learn in coaching is when you become a leader, especially as you move up that chain of leadership, and now you're becoming a more important leader initially, like your whole life, you're saying your opinion, you're talking, you're getting a gold star and a hundred whatever, you're very successful. Great. And then you become a leader.
Carol Cone:
That is very powerful. I'm curious about what is the role of humility in leadership today? So how do you coach for that? Are you asked for that?
Scott Osman:
Yeah, so I love that question. Internally within the company and in your role as a leader. I think humility is one of the greatest strengths of a leader. Actually, we were talking before Hubert Joliet, great story of humility. He was brought in to Best Buy when I think Best Buy was one of the last big box electronics retailers. And it was just assumed that Best Buy was also going to go out of business.
Carol Cone:
Right. Six months and gone.
Scott Osman:
Six months and gone. And he went in and he's super smart guy, has all the answers, very successful career, McKinsey and Harvard, the whole thing. And he comes in, he can't figure out the problem. And so he goes to the stores and Marshall was his commercial, I think helped coach him to this. And he goes to the stores and he's talking to the people and he says, look, I'm Hubert Joliet, CEO of Best Buy. I don't have the answers to help us in this problem. I need your help. And that was it. And he became known for raising his hand, I need your help. And because he did that, he heard from the people at the front lines what actually was a possible business idea that would say Best Buy. And it did. He took the advice of the frontline workers and understood what the customers really wanted and had the humility to go with their insights instead of his intuition. And of course, Best Buy continues to be a thriving company.
Carol Cone:
And I love the fact that he said, when someone comes in, don't sell them something. Listen to what are their needs and become relational with them. And he became relational with the blue shirts, and the blue shirts became relational with their customers, and they were then seen as problem solvers. It's a great, great turnaround story. And so let's pivot a little bit or go to the role of corporate purpose today. And so very curious about when you're coaching your leaders, no matter what industry they are, public or private, how important is it having a distinctive purpose for them today?
Scott Osman:
Yeah, well, look, Carol, you and I go way back in the whole world of purpose. So I have trouble hearing any leader without thinking about purpose. But the truth is, at its core, purpose is understanding where you stand. Where are you grounded? How do you direct yourself? It always includes, I don't know why we always have to say this, but it always includes making sure shareholders are well represented, they're always well represented, but understanding that a lot of the things that we think about as being in opposition are not an opposition. And having a purpose helps you see, not that they're in opposition, but they require creativity to see it all fit together. And purpose gives you that creativity to be able to say, we're going to do this. It's in alignment with everything we stand for, and that's important to us.
Carol Cone:
I wanted to ask you, let's see, because getting onto the bottom of this, but I love the conversation, the role of creating the richest cultures, the cultures that truly exude their attitudes, their character. What's the best way for leaders to do that?
Scott Osman:
So any behavior that you want other people to follow, you have to be the example of that behavior. If you want to have a culture of humility, you have to be humble. If you want to have a culture of generosity, you have to be generous. Don't expect that you're going to tell people to do one thing and then show up differently. They follow your actions every day.
Carol Cone:
It's almost like a young child looking up to their parents with great affection and love and What do you want me to do, mom? What do you want to do, dad? That's why I asked that question very much in the beginning, what really impacted you as a child? I always say that the speed of the leaders, the speed of the troops, not that they're going faster, but then how they are marching forward. So it's fascinating in our current political environment for sure. As we get to the bottom of this, what's one leadership myth you wish you could retire forever?
Scott Osman:
You know what, the first one that comes to mind is that leaders need to be the smartest guy in the room.
Carol Cone:
Great one.
Scott Osman:
And I think too many leaders believe it. I think that's a huge Achilles heel of a leader. Leaders, almost by definition, cannot be the smartest guy in the room, right? Because they're not going to know everything about everything. That's not the role of leadership. Leader has to be the visionary to say, this is where we're going, and bring people around them who can help them get there. So being the smartest person in the room, love to retire that.
Carol Cone:
Okay, you have another one you want to retire? That was a good one.
Scott Osman:
The myth that you want everybody to be like you. The myth that for me, the reason why I'm struggling with it, so not a myth for me, because I believe so in every cell, that diversity creates strength and creativity and all the things that you need to be successful in a company. And yet I feel like the mythology of the leader picking subsequent leader, that's exactly like them should be retired.
Carol Cone:
That's great. So as we close, it's been a great conversation. I love it. What's the next frontier for leadership growth?
Scott Osman:
I don't think purpose has ever gotten the full due of the impact that it has. And it also, I think in a lot of ways, purpose, purpose holds the multitudes of leadership. Sometimes we think about purpose too often people think about purpose in too narrow a box and to think purpose is doing good. And I think that's just one part of it.
I think purpose is really having a vision of where the company's going to go. A vision that includes, sure, success for the stakeholders, but also nourishment for the employees so that you get the best employees so that you are a good citizen in your communities, so that the communities welcome and celebrate the fact that you're in their community, whatever that means, so that you can create more flourishing, human flourishing. I think that people are going to reward those companies that really embrace that.
And I think the idea of human flourishing, and by the way, I'd almost say not just flourishing, but generational, flourishing. It's important to think we're not just doing things for ourselves and the people around us today, but we're also thinking about the people generations from now that are going to be living with the consequences of our decisions. And I Fundamentally don't believe that those things are in conflict. I think as leaders, that's where we need to be thinking and growing.
Carol Cone:
Love it. Love it. But this has been an amazing conversation. I always give the last word to my guest, so you can say something already sad or you want to add a boy to our listeners or anything like that.
Scott Osman:
Well, if it's okay with you, I just say you, Carol, have been a brilliant inspiration for me. I have known about your work for decades, even well before I got into purpose, which was a long time ago now. I just have always been inspired by your creativity and innovation, the way that you bring other people together. I'm so delighted to be in conversation with you today.
Carol Cone:
Oh my God, thank you, thank you, thank you. That was so kind. But Scott Osmon, who's CEO of 100 Coaches, a coach and a coachee, and a wonderful, marvelous human being. So thank you so much, Scott. It's been a joy.
Scott Osman:
Likewise. Thanks, Carol.
Carol Cone:
This podcast was brought to you by some amazing people, and I'd love to thank them. Anne Hundertmark and Kristin Kenny at Carol Cone ON PURPOSE. Pete Wright and Andy Nelson, our crack production team at TruStory FM. And you, our listener, please rate and rank us because we really want to be as high as possible as one of the top business podcasts available so that we can continue exploring together the importance and the activation of authentic purpose. Thanks so much for listening.
This transcript was exported on Nov 11, 2025 - view latest version here.
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