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Becoming an Olympic-Level Leader Through Coaching With Sherry Winn

Sherry Winn

Sherry Winn is the Founder and CEO of The Winning Leadership Company, a firm specializing in developing leaders who inspire their teams to work at championship levels. She is a two-time Olympian, National Championship Basketball Coach of the Year, and a three-time Amazon best-selling author. Sherry is also an internationally renowned speaker who frequently addresses audiences such as StubHub, AnyTime Fitness, New York Life, Edward Jones, and Technicolor.

Here’s a glimpse of what you’ll learn:

  • Sherry Winn explains how The Winning Leadership Company helps people 

  • The correlation between sports and business 

  • Qualities of a good leader 

  • Sherry talks about her leadership style 

  • Pivotal moments to becoming a better leader

  • The power of being emotionally aware as a leader 

  • Techniques for dealing with bottled up emotions 

  • The Winning Leadership Company’s customer success stories

In this episode…

Leading a team is no small feat. It requires a unique set of skills and qualities that not everyone possesses such as finding top talent, maintaining high loyalty, and taking your team to the next level. This is where working with a coach can be helpful.

With over 34 years of experience as a national championship basketball coach and two-time Olympian, Sherry Winn acknowledges that coaching is not just for athletes or performers. It's for anyone who wants to improve their skills and reach their full potential. A coach can help you understand who you are, how you appear to others, and what you need to do to increase productivity. With a coach, you can become a better leader and build stronger relationships with your team.

In this episode of The Customer Wins, Richard Walker sits down with Sherry Winn, Founder and CEO of The Winning Leadership Company, to discuss leadership strategies that create Olympic-level teams. Sherry explains how The Winning Leadership Company helps people, the correlation between sports and business, the qualities of a good leader, and her pivotal moments in becoming a better leader.

Resources mentioned in this episode:

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Episode Transcript:

Intro 0:02 

Welcome to The Customer Wins podcast where business leaders discuss their secrets and techniques for helping their customers succeed and in turn grow their business.

Richard Walker 0:16 

Hi, I'm Rich Walker, the host of The Customer Wins where I talk to business leaders about how they help their customers win and how their focus on customer experience leads to growth. Some of our past guests have included, eTreme and ACOM, and even the Austin Technology Council in the city I'm in. Today I get to speak with Sherry Winn the CEO of The Winning Leadership Company, and today's episode is brought to you by Quik!, the leader in enterprise forms processing. When your business relies upon processing forms, don't waste your team's valuable time reviewing the forms. Instead, get quick using our Form Xtract API. simply submit your completed forms and get back clean, context-rich data that is 99.9% accurate. Visit to get started. Now before I introduce today's guest, I have to give a huge thank you to Chris Zuczek, the Chief Product Officer at CAI S for introducing me to Sherry. If you are in the world of alternative investments, you need to know CAIS go visit for more. Now I've really been looking forward to introducing Sherry Winn on this podcast ever since I met her and once she starts talking I think you'll know why. Sherry stepped into the world as a leader first in sports where she attended the highest level possible athletics the Olympic Games. She then led college basketball programs for 23 years where she won a national championship and took her teams to three Elite Eights. Since 2012. As CEO of the winning leadership company, she has delivered over 3700 hours of leadership programs where she has developed Olympic-level leaders. Sherry has spoken audiences as large as 14,000 and has spoken for companies such as Dell, Hitachi, and Adobe. She has spoken in Gillette Stadium airplane hangars, baseball diamonds, and too many hotel convention centers to mention organizations such as the Volunteers of America, Florida Chamber of Commerce, Edward Jones, and a host of multi-million and billion-dollar companies invest in Sherry's teachings each year. She's also the author of an Unleash The Winner Within You, Sherry, welcome to The Customer Wins.

Sherry Winn 2:23 

Thanks, Rich, I'm so thrilled to be chatting with you. Because I know who you are. And I know that we have a lot of great things in common. So I'm really excited about our conversation.

Richard Walker 2:32 

Me too. So if you haven't heard this podcast before I talk with leaders about what they're doing to help their customers win, how they build and deliver a great customer experience and the challenges to grow their own company. Sherry, we want to understand your business a little better. How does your company help people?

Sherry Winn 2:48 

So is The Winning Leadership Company. So our focus is on helping people achieve that Olympic-level success or Olympic-level mindset so they can achieve unprecedented success. So whatever we do is work with leaders so that they understand who they are, how they appear, what do they need to do to double their productivity, get higher engagement scores, get their people motivated, so that they can be happy, be happy to enjoy work, which obviously increases everything else that goes on in the business.

Richard Walker 3:17 

So you come from sports, how does sports and business correlate? How do you bring those two together? And you're talking to a non-sports guy, by the way.

Sherry Winn 3:28 

Well, so businesses are made of leaders and teams, right? And cultures, same thing that a team is about, like you have to have great leadership to make the teamwork, you have to have that team unity, that team commitment, the team culture to make it work. So anything that I've learned from all the people I've interviewed for my last book for the upcoming book, including you is really that, that there's not any separation between the ideas between a corporate team or makes it good corporate team in a good corporate culture, and an athletic team. Those are exactly the same. Right? So the crossover there is really huge. And it's all about people, I mean, people and relationships. So, any kind of business is about relationships, if you don't have good relationships, you're not gonna have a good business. Right? So that's really the crossover there. It's exactly the same. A good leader is a good coach, and a coach is a good leader.

Richard Walker 4:16 

Yeah, I think you're right about that. Because I don't like when I'm called boss, because I think of a boss is somebody dictating and telling you what to do. I like to be the leader, where I'm collaborating and helping people see different things and have different perceptions and perspectives. So I'm curious then if you're focusing on leadership, are you really focusing on the person and their own personal growth then?

Sherry Winn 4:39 

So it can be focused on different ways. So it depends on what the company is wanting. So as a company wanting to build a winning culture, so that's a little bit different, right? There's those times that you have to get your leaders all on board that the leaders don't have to think the same way you've got to get them synchronized and their vision. So that's one thing. The other part is really part of that building winning culture is building your winning leader. So there are different kind of ways to go about it. But in the end, it's really about you have to get the right people in the right roles, so that you're going to win. Right? If you don't have the right people, the right roles, you're not going to win. Part of that is making sure that people that are leaders, they have the right mindset, so it's about, it's not about me, it's about you, right. So as a leader, you have to understand this is about the team, it's not about you, which that means you've got to reduce your ego, your ego is gonna go in the back seat, so that you can have the right vision, hold the right vision, keep the people aligned with the right vision and empower your people. If you can't empower your people, there's no possible way of getting to success.

Richard Walker 5:39 

So I've often read about different leadership styles. And I'm wondering if you think one style is better or more effective or more productive, or how you look at somebody and help them develop their style?

Sherry Winn 5:51 

Well, so I think that you have to be you, right? So you have to be authentically you. And I think a lot of people don't know who they are. So you have to know you to grow you right. And so that taps into that self-awareness piece, which I think is the most essential thing that you do as a leader. And the best leaders are very, they have a very high emotional intelligence quotient, right? They're very high in their eye, their emotional intelligence. So what does that mean? That means that you have to work on that self-awareness piece. And the more that you work on that the better leader you are. So how do you grow that? Well, that's self-reflection. That's understandable. And not just self-reflection, but asking other people. And one of the things I tell good leaders is, ask, how do you know what a good leader is? And they'll start telling me, I said, what do you ask your team when they want it from you? Well no, well, how do you know? Right? I mean, you've got to get there, you've also got to respect and get their information coming into you. So if you add, like, their top seven qualities, they want a leader, and you put that next to your desk every day. And you just ask yourself, like, at the end of the day, I have one-minute reflection on a scale from one to 10, how did I do it each of these characteristics, oh, man, I was a six on listening today, I've really got to work tomorrow on being a better listener. So if you're thinking, and you're self-reflecting, and you're being in that space, you're always gonna be better because you're constantly working at being better. And you're constantly aware of other people. Right? And how you show up in that. So that's one of the things I love to talk about the most is, do you know who you are? Do you know how you show up? Do you know what your thoughts are, that are disturbing you they're stopping you, in limiting you from moving forward. And I think that's one of the things you love to talk about Rich is really those self-limiting beliefs that we have?

Richard Walker 7:32 

Absolutely. I mean, I've written a book, called, It's My Life, I Can Change If I Want To. And it's a four-step method of how to create personal change. But at the core of it, it's identifying beliefs. And there's this magical thing that happens if you can identify a belief that's not working for you, I promise, you will not choose a worse belief, you will only choose a better belief to empower you to do more in your life. So I have a lot of different questions around this. Going back to leadership style, I do agree with you, it comes to the personal like what kind of person you are. And I've been with the kind of person who's a cheerleader, and it's rah, rah, rah, but they don't necessarily care about me. They care about their vision, not only their vision, they're trying to motivate you to go that way. Personally, I try to be a servant leader, I try to seek to understand and I try to help empower others to do what they do best. So how would you describe your own leadership style?

Sherry Winn 8:25 

Well, I think when you say leadership style, I think the first way is to find authentically you and when I mean that, you can't help but be a servant leader if you know who you are authentically, right. If you're really diving into the pieces of you, that are not productive, that are limiting, that are stopping you from being the best you. So when you show up as a leader, I think they're all aspects of you. Right? Are you the cheerleader? Yeah I can be a cheerleader? Am I a motivator? Absolutely. But the number one thing is that if I understand me, and I really have come to the place of knowing me and loving me now this is a big part. I think a lot of people don't love themselves, right? They say they do. Oh, of course I do. I love me. But it's really loving you. When you to the place that you honor you is that collect that self-actualization model, right? So as you grow up, and then that top part is you really live in that space of self-validation. When you no longer need that people around you, to validate you, you're in the perfect space to be the servant leader. You can't get there. You can't just go and I'm gonna be the servant leader. You've got to first not have the need for other people to tell you how good you are or to serve you or to make you feel better, because all those inhibit you from being the best you and being the best leader.

Richard Walker 9:46 

Yeah. So I don't think that you were born with all this knowledge. I have to imagine there were some strife and some challenges that made you go wait a minute, I need to do better. What was one of these pivotal moments for you that said, I can do better.

Sherry Winn 9:59 

Oh man, I often tell people like you would not have liked me, if you would have met me in my 20s, or my teens, right? You wouldn't have liked it. I didn't like me. So you couldn't have liked me, I didn't like me. There are so many moments that we get opportunities to get better or to get better, better, right? I mean, many people choose better. And they get mad and angry. And they can relate like, this has happened to me. And this happened to me, and this happened to me. But I really think that everything in my life was perfectly designed for me to improve. Now, having said that, I didn't do that.

Richard Walker 10:33 

Easier said than done.

Sherry Winn 10:34 

I feel a lot of my life angry. But I think the very last big event that occurred to me was a developed chronic pain at the age of 35. So I was an athlete always identified myself as an athlete still live like an athlete, and I was still running and lifting weights and, and you know, biking, and rock climbing and all those things. And then age 35, I developed chronic pain, I couldn't sit stand or walk without pain. So I literally went from this athlete to this couch potato, like, boom. And I saw 17 different medical professionals had every test known to mankind, and nobody knew, like there was no diagnosis. And the last group of doctors that I saw, they said, well, all we can do for you is, we'll teach you how to manage your pain. And I was like, you don't get it, I don't want to manage it, I want to live pain-free, this is not an option for me, right? With that process, because then I went away from Western medicine, and I went into some alternative medicine. And part of that was these therapists who were like, okay, your body, mind, and spirit are all connected. So your physical pain might have elements of a spiritual element, it might have elements of emotional and there might be true physical elements as well, we need to address all three and I'm like, You're full of crap.

Richard Walker 11:54 

It's all physical.

Sherry Winn 11:56 

It's all physical. Right? I don't know why you're talking emotional. But that was really the turning point. Because I wanted, pain often causes us to look differently, to open our minds to different things. I was in so much pain, and they made me feel a little bit better. So I was willing to open up my mind to the possibility, look, there could be something to this idea of the emotions that I have stuffed forever and haven't ever dealt with. It could be some idea, this spirituality piece that I have dumped. And so this is a bunch of crap, too. So there could be some possibilities there. Let me start opening my mind. And so that was really where my new learning came. Right. That's when I started opening my mind to other possibilities. I started reading tons and tons and tons of books. And I had to get real, like I had to really look at myself in the mirror and say, Do you like who you are? I couldn't even get to the word love. Do you like you are? No, I hate me.

Richard Walker 12:48 

Wow. That's tough to get to that point. Yep. And what you're opening up here is what I would define as what self-awareness is derived from, it's being open-minded. It's being open to all the possibilities. So I'll tell you a story in college I was exceptionally poor. I had many weeks when I woke up on Monday with exactly $5 to my name, had to get to Friday for paycheck had to find gas and parking fees and food and had to figure it out. Right. So one of the things I challenged myself to do is ask myself, what are all the options to get money? Now normally, we think about the positive options like, well, I could borrow the money, I could earn the money, I could do a focus group make 10 bucks. But what about the negative ones? I mean, if you really want to be self-aware, you have to open your mind to all the possibilities. So I have a simple rule, which is, for every choice I'm gonna make, there are 43 options, I could choose why 43 is just a sufficiently high and random number to challenge me to go beyond yes and no true and false. And so then you start saying, oh, I could steal the money. I could sell something I don't want to give away. And I'm not saying I'd go steal the money, but to challenge yourself to be open-minded. So I think pain is the ultimate motivator here that caused you to get to that point. And with that open-mindedness you sounds like you embarked on a journey of lots of studying and introspection.

Sherry Winn 12:52 

Yeah. And this was a thing as, I did get healthy. And I never took a drug and never had surgery. So neither of those things ever, never, ever in all that journey. And it was a really long journey. Seven years, but I never opted to take a drug or do surgery. Mainly because surgery, they're like, it's 50% successful. I'm like, I'm not doing that, like 50% of that number. And I didn't want to do drugs, because I just didn't want to add another element of something, right? Oh, here's the side effects. Here's these 10 side effects. It'll make you feel better here, but you're gonna get x. I was like, I'm not gonna do that. So it really came down to let me open my mind like you said, let me really open my mind to these other possibilities and let me start exploring, what do emotions really do to us or do they do for us? And we tend to not understand the power of emotions, even when people will understand. If you go to the doctor, and they say, you need to reduce your stress to help your heart, people get it oh, yeah, they were dismissed, they all get that. But they don't think of stress as an emotion or what is stress if it is not an emotion it is, it's full of emotions. So we don't tend to understand that because we're just not taught that way. But once we really start examining our thoughts, our thoughts lead us to actions are actually just into our habits, our habits become how we show up every single day, right. And so people who can't change is because they're unwilling to acknowledge the thought habits that they've had over time, that have led them to the behaviors that they continue. And they think they're creating new behaviors, but you can't create a new behavior without a new thought pattern.

Richard Walker 14:06 

Man, you just articulated something for me I've never articulated and it's given me clarity, which is that stress is actually driven by the emotions. And I feel like I live a very stressless or no stress life, my brother-in-law came into my office, once when we had an office, he's like, this is like a Zen library. It's so quiet and peaceful here. And it wasn't that people weren't interacting or engaging with things or customers weren't upset at times. There's just like, oh, let things roll. And I just never articulated as driven by the emotions you have towards what's happening. And I love that Sherry.

Sherry Winn 16:09 

Well, we don't know. But we don't even recognize because we pattern ourselves after our parents without even knowing it. And how many of us have said, I'll never be like my mother, I'll never be like my father, right? And you go back 30 years later, you're like, oh, crap. Like, I'm just like him. And it's not saying they're bad. And I want to say that. I'm just saying that what we learned at an early age is so deeply imprinted in our brains and the way that our brains work, that we follow those patterns without knowing it. And every time we follow a pattern, we reinforce it, and pretty soon, we're not making original decisions. We're just following a pattern of behavior that we heard and saw when we were young. And it's amazing to me, like, I'm so curious now that, I'm older, my parents are older that I go, and I listen to them. And I'm like, oh, my gosh, like, that's why I did that. Like, that's why I said that. That's what and it's not like, I'm not judging now, they only do what they knew, right? That's all we all know. But we only do what we know, until we open up more possibilities and more doors. But to get out of that we have to be willing to take the time to change who we are, like you did, right. And like many other successful people that I know all these people I've interviewed for my books, almost every one of them recognize that power of self-awareness and the power of changing who you are and your limiting beliefs. They all get that. And people who do not succeed in life are trapped in those old thought habits that they got from being a youngster.

Richard Walker 17:43 

Yeah, that somebody else said this to me recently, which is something to the effect of your business's growth is determined by your personal growth. And I can account for that, frankly, everybody kept saying Rich, you should read books, you should read books now. So one of the things I suffered from in my 20s and early 30s was smart kids syndrome, as I like to call it, I'm smarter than everybody, I don't need this, I don't need that. And I just reject things out of hand. The other side of it is I don't like to read. I just get too distracted to read. So I discovered audiobooks. Oh my gosh, I started devouring book after book, one or two a month, three a month, sometimes things changed. Oh, my gosh, my business started to grow. My team got better, more engaged. It was amazing, because of that personal development that you're talking about. Right? So I hope our audience is hearing this and they're saying to themselves, okay, what pattern have I not acknowledged? What awareness am I not open to? What am I not being open to as a possibility? Because you're right, I mean, going back to things like spirituality, your emotions, how would that affect you physically? Come on?

Sherry Winn 17:43 

Yeah. Not affects you physically. So, it's amazing how many emotion I stuck, like I stuffed on because, hey, you're tough. You're an athlete, you're not supposed to feel anything, those kinds of things. And so I learned and not only that, like, in our family, we didn't talk about emotions. But there was no discussion of emotions. It was like, you're alright. Quit crying, you're tough. Like, I mean, they meant it in a good way. They wanted us to be tough and, and that kind of thing. But I didn't know how to feel an emotion because I just stuffed them where your body can accept this, like anger and anger and anger and abandonment and betrayal and all the feelings that we feel like at some point, it just goes, I'm done. And you've got to do something different. And so it was really hard for me, like Russia won't tell you how hard it was for me to even talk about any emotion to even talk about it. Right. So these are therapists that I work with, they would say, okay, let's talk about like, when you were 13 and I go, No.

Richard Walker 19:51 

How can we help you?

Sherry Winn 19:53 

No, I would shut down and I'm gonna I'm gonna go and shut down like I would like put up barricades. I'd have like a castle with a moat. and crocodiles, and there's my army. Like, you're not going to get through me to any discussion. So it took me a long time to feel that I could even say, this is why I was so angry, or this is why I was so hurt, or this is, it was so freeing. Oh my gosh, like at the point when I finally could talk about like, why did I? I was so hard. Was so hard?

Richard Walker 20:28 

Yeah. All these fears bottled up around what that emotion meant, right? Yeah, that's incredible. You know, somebody asked me recently, which caused me to make a breakthrough two weeks ago. And it's been an amazing breakthrough for personal and I think business reasons. Which was, why am I pushing so hard against something that was acknowledging something and trying to stay away from it super hard? Why? And that was the technique that made me realize, oh, my gosh, there's something here I'm gonna dive into? Do you have a favorite technique or go to technique when somebody is bottled up and challenging?

Sherry Winn 21:01 

No, I think the first thing is you just said something, which is a universal principle is what we resist persists, right? So whatever it comes at us, and we tend to push it away. I don't want to deal with it, that is going to keep coming. Right? So Right. And if you really examine your life, you'll know like, similar things keep coming at you, right? Like, why do I have keep having the same kind of crazy boss? Why do I keep in this same relationship, like I divorced this person I'm married to do and they're the same person, I didn't even see it, but they were in the same relationship I was in. So it's because we're not willing to like, step into that and learn from it. So the first thing is to understand that universal principle, like what we resist persists. So we might as well meet it right where it's at, we might as well just walk them at like, hey, come on in, like, let's talk about this. Let's meet you where you are. Let's examine this, let's fill this what are the feelings I have around this? How is this particular thing that I'm doing, how is it becoming problematic? And how is it showing up in all those different areas in my life? And it's something like kind of like the technique that you use in your book a little bit different, just because how's it showing up? Like in what was it shown up? Is that a positive view is a negative is how's that helping you? Who would you be if you didn't have that? Like, how would that further your life, if you didn't have it? Let's future pace. Let's think about the good stuff. Because I think that we get locked into the negative, the negative, the negative, this is what I feel this is not showing up, and we've got to get out of that to think about the future pacing. So yeah, just acknowledging like, how is it a problem for you? And how's it showing up? How's it hurting you? And you do that in your book? You stayed a little bit differently. I love the way you stand it. Yeah. What are the consequences? This is spring for you? And for others, I think is the way you say it.

Richard Walker 22:41 

Yeah. Who is it impacting? How does it manifest? When does it come up? Where does it come up? I think those are all honest questions. I actually in my book, also say don't ask a why question. Because your brain is wired to answer every question and why is so destructive? Why can't I lose weight? Because you're lazy? That's not a great answer. When can I lose weight in the morning in the evening? How can I lose weight? Go to the gym, eat less?

Sherry Winn 23:06 

Yeah, those are great questions, right? Because of why is always insinuates kind of this negativity. Like even when leaders are saying, well, why did you do that? Oh, yeah. So let's say that person, like you're stupid, so it's not a good question. It's not a good way to ask a question. So you're correct in that, yeah. So everything I do really, with leaders is, let's get more self-aware so that you can show up authentically so you can show up in this. In our eyes authentically. I think we're all authentically love. It's just that we have negated that we haven't allowed ourselves to be that, well, man, if you want to lead from love, it's a whole and I don't mean like, Chrissy, mushy like, I'm talking about like, the place of compassion and empathy, where I really, really care about you, and further in you and helping you become the best version of yourself, who doesn't want to work for that person?

Richard Walker 23:58 

Yeah, one of the things I learned and talking to people like yourself through this podcast is that if you want to build the best customer experience, you cannot do it if you do not love your customer first. So coming from that place of love, and I think that your inside talks to the outside, so how you treat yourself, therefore how you treat your own team, is what's going to manifest for how you treat your customers. So, to love your customer, means you have to love yourself and your team and the process and the problem and solution. Not just oh, I love this guy because he's cool.

Sherry Winn 24:33 

No, no, no, no, I agree with you. 100% like it first comes from you. You can't give what you don't have, which is what I believe that, training and leaders coaching them and given their highest opportunity to really get that like you can't give what you don't have. So if you don't have compassion, you can't give it, if you don't care about you, you can't care about others. Right and so it shows up throughout your entire, gonna show up through every conference. issue you have is going to show up through every experience connection you have every network you have every time you have a conversation with a team or a client. And so that's why they like you said it's from the inside out. So let's heal and help you heal the inside. And some people don't want anything to heal. I'm like, I've never met a person that doesn't have something they need to heal.

Richard Walker 25:21 

Yeah, no, that's so true. That goes to the imperfect nature of who we are. And the fact that I'm 49 years old, and I just discovered something that I chose a belief when I was 18 that has been manifesting in the wrong way all these years. And suddenly I lifted and I feel like a cloud has been lifted. And I've got a whole new perspective tells me that there's a whole bunch more, I'm probably missing.

Sherry Winn 25:43 

I love the way you see, I chose a belief. I mean, how wonderful to know that we chose it, because if we chose it, we can release it. How wonderful to know that. And so it's so powerful to say I chose this belief, I chose to believe this way, which then manifested all these events in my life, and now can choose a different belief was going to bring me all these other wonderful things that are coming in. And you're right. I mean, it's a never-ending story. So never never-ending journey was never a journey of ours is to learn a little bit more about ourselves, right? And to dive deeper into greater knowledge and awareness.

Richard Walker 26:18 

Yeah, for sure. So I'm wondering if you have a favorite success story to talk about with a customer that you helped transform and what happened for them as a result of working with you?

Sherry Winn 26:27 

There is. I had a CEO who called me and he said, I want you to coach my CFO. And I said, great, tell me more about it. He goes, well, he just lost us a million dollars. Like, dude, I can help you. Because really, I said, yeah, fire him. Because obviously we love him, but you don't have to pay me you don't have to pay him. And we kind of laughed because it was meant to be a joke. And we laugh. And I say well, sure, I'm happy to work with this guy. I just started work with him. And about a month later, the CEO called me back and said, what happened? What do you do? And I'm like, oh, I was thinking, did he lose more money? I said, well, like we've been having some great conversation. He said, no, no, he just got his million dollars. So tell me what you did. So first of all, you owe me more money. He made us 6 million you can pay. But I said don't really, it's just a matter of discovering what he was doing. And what he was doing is he was, we all have this need, there's a need to control. And when we have a need to control, it's out of fear. So instead of doing like he was doing too much, he was interfering with all of his people all the time, like he was in the weeds doing all that stuff. And the reason he was doing that is because he needed to control the reason he needed to control because of the fear that he had. Right about, always about fear. So we work through that he was able to empower his team, right, which allow them to go on and do more. And then he could focus on other things that were outside of his team, right. So he wasn't having as little micromanaging, he was able to focus on other things, and therefore able to impact the business in a totally different way. So, it wasn't just a matter of going in and go like, I like sent my fingers and you're done. It was really his willingness. Let me say this first, his willingness to examine what he was doing and why he was doing it, and to address the underlying fear, so that he could change and empower the people around him and empower himself.

Richard Walker 28:21 

I love that. I love that. I view my company as empowering people to do their best work. And I didn't really learn that until I had my first child, because I went from working 80 hour weeks to 35 hour a week. And that was my choice. I said, I wanna spend time with my kids and my family. But doing that I felt all this guilt and shame of not producing not doing the work. But what it forced me to do is finally delegate properly. And guess what happened, Sherry, we started growing like crazy. It was amazing. I got out of the way finally.

Sherry Winn 28:51 

That's that point, though. Have you reached the point where you didn't feel like you were necessary, right. And that's hard, because we have to release that kind of ego that thing to say, other people can do what I was doing. Like that's ah, but you can't do that. You can't do that if you're not already the place that you know, you're worthy. Like you truly know your worth. Yeah. And then you don't need anybody to tell you it feels good. Like I'm always gonna welcome somebody saying, hey, thank you. I'm always gonna welcome that. I just don't need it anymore. Yeah, like, I'm not looking for somebody else to validate me. I don't need that anymore.

Richard Walker 29:27 

That's such an important stage to be at. And unfortunately, so many people never reach there. I know that. The other favorite part I have about your story about the CFO losing million dollars is the idea that that was a lesson he learned that cost the company a million dollars, why would you fire the guy who just had the most important expensive lesson ever and give them to the next company?

Sherry Winn 29:53 

Well, and kudos to the CEO right? He was willing to invest instead of just fire I mean really willing to invest and say look I'm gonna give him a chance to learn and to grow. And I want to figure out what it is that we can do to make this different for our company and for him, and given him that opportunity. Now some people look, I'm not gonna say there's a success story and everybody I work with, because that would be a lie because it's not based on me. All I'm doing is giving you the opportunity to to grow and learn, you have to be willing to do the work. I am not a magic. I'm not a magician. I don't have any that magic fairy dust I can throw out there. But I can't help people recognize what they're doing to themselves so they can change?

Richard Walker 30:31 

Yeah, yeah. So let me ask you one more question. Before we start wrapping up here. Tell me about your book. Tell the audience about your book.

Sherry Winn 30:38 

So the most recent book that I wrote, I'm gonna show it is this is called Winning Leadership, Seven Secrets to Being a Truly Powerful Leader. And this came about from interviewing over 200 leaders. And so the question or the questions I asked was, what's the biggest challenge you've ever faced? And over 80% of those people said myself? So it developed the first chapter, which is called the winning factor, which is all about self-awareness. Right. And it was just so fascinating to listen to these people. And it really changed. Like, I started with the idea that, there's so many poor leaders, and we need better leaders. And I discovered through the people that I interviewed, there's a lot of good leaders out there, maybe there's still some poor leaders out there doing the wrong thing. But there's so many good people who have taken the time to invest in themselves who have had coaches who have hired, have gotten mentors who have read books, who've listened to books, who've done self-reflection, who've done the work, there are tons of those good people out there. Right. And so they gave us information to share with other people so that, no matter where you are, if you want to improve, there's an answer for you in the book for you to get a little bit better, right? And doesn't mean that you go from, oh, I'm at the bottom, I got the top. I mean, you could be like a silver medalist and you just want to be a gold medalist. So you got to do that work to increase your possibility.

Richard Walker 31:57 

Yeah, for sure. Okay, I don't want to wrap up. I have another question. What is the difference between a silver medalist and a gold medalist?

Sherry Winn 32:04 

Man, you know what is like? Can you think about the Olympics? It could be like a point 01 second.

Richard Walker 32:10 

Right. Yeah, it's so fractional.

Sherry Winn 32:12 

It's fractional. So what is that difference? And I think it's the mindset, I really truly believe it's the mindset. So it's the person who can get their belief system aligned with a goal. And I don't think a lot of people can actually do that. I think that a lot of people want something. The reason they can't have it is they cannot align. And if people say, Oh, I'm aligned with it, no, you're not if you're aligned with lose it, you'd be living it, if you were totally in alignment with it, you'd be living it. If you really listen to your inner voice and be like, well, you may not be smart enough, or you don't have the background or you didn't graduate from x, x, x University, or you don't have the right network or like, so you want it. But like that difference is really, is your goal aligned with the belief system? Are you in congruence to that, if you are, you're living it.

Richard Walker 33:05 

So that can be as simple as if you want to, let's just do something simple. You want to increase your strength, and your bodybuilding or something, you got to eat the right foods. And so if you start eating the wrong foods, you're not in alignment with the goal. I mean, it could be as simple as that, right? I'm sure there's way more nuance to the Olympic athletes.

Sherry Winn 33:24 

Well, it's really, I think it's the belief system about you. Right? I don't know if you watch women's basketball, but there's a woman there's a phenomenal right now called Caitlyn Clark. So Caitlyn Clark is rewriting the rules for playing basketball. She shoots for the logo. So she's shooting, wherever else is shooting the three-point line. She's like six feet back and making them consistently, consistently. So and you look at her, you look at her body, and she's like, she's not overly muscular. She doesn't have this incredible job. I mean, she's not super-fast. I mean, she's good. But what makes a difference between Caitlin Clark and everybody else in the world, right, is simply that she believes that she can shoot the ball from anywhere and make it she really, I mean, she literally believes that. So when you watch her play, you start wondering, like, What in the world? What does she do to her mind? Who convinced her like that she could do these incredible things because she's on this. Right now. She's the second all-time leading scorer ever in Division One basketball ever. And she's got nine more games and she'll, unless something happens, she's gonna top that and be the all-time leading scorer. So what is it about her? Right, because you'll get other people. They're faster, they're more athletic, they can jump through your man. Right there.

Richard Walker 34:37 

That is powerful stuff, Sherry. That is awesome. All right. So look, we got to wrap this up. And before we do, I have another question. But what is the best way for people to connect with you and find you.

Sherry Winn 34:49 

So whether you want your business to get, if you're struggling with a winning culture, and you'd like to have that or you really want to have that unprecedented success from your leaders, whatever that is, looks like for you, you can find me at That's how you can find me. And if you want to have a free discovery call, like I always happen. And I don't pitch look, I'm not personally through the whole conversation pitches you. I'm a person who after the call is over, you're going to have three takeaways that will help you immediately with your business immediately guaranteed, right? So if you'd like to do that, you just email me at

Richard Walker 35:29 

Outstanding. That is awesome. All right. So I had a ton of questions. But my last question is who's had the biggest impact on your personal leadership style, and how you developed?

Sherry Winn 35:39 

Everyone wants to stay a positive person, but I want to say to you, that it was a negative person, and it was my 1984 Olympic coach, because over the course of the three years of playing, I never got a single compliment. I never got anything that helped me. He often called me stupid, Sherry, you're so stupid, stupid, you're stupid, like, this is what I got. And I knew going through that, that my skill level dropped, because I believed in him. So instead of helping me find my best version of myself, he actually took my skill and I was less then, because I didn't have the power to not believe him at that point in my life. So I think about all the lessons that he taught me, right, it wasn't like, oh, all these great things. But all the things not to do like everything that I should never do as a coach or as a leader. I had a whole big Journal of them, right? Like you talked about 43 things not to do, I could probably have 143 things not to do. So when you looked at, go back to better or bitter, the first I was bitter about it. And then I recognize the true gift that he gave me through all of that, because it really transformed the way that I looked at leadership and the way that I lead.

Richard Walker 35:39 

Man, I'm so glad you said this, because you're right. Most people seek the positive in this, but I would say the contrast is equally important. And I kept working at different places through college to find what I liked. And I only found what I didn't like. So when I did see what I liked, it was in contrast, I could actually identify it more clearly. That is brilliant. That is totally brilliant. Thank you. Well, look, I have to give a huge thank you to Sherry Winn the CEO of The Winning Leadership Company for being on this episode of The Customer Wins. Go check out Sherry's website at And don't forget to check out Quik! at where we make processing forms easier. I hope you enjoyed this discussion as much as I did, and will click the like button, share this with someone and subscribe to our channels for future episodes of The Customer Wins. Sherry, thank you so much for joining me today.

Sherry Winn 37:43 

Thank you Rich is fun. Lots of fun.

Outro 37:46 

Thanks for listening to The Customer Wins podcast. We'll see you again next time and be sure to click subscribe to get future episodes.


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