Winning Strategies For Teams With Sherry Winn

by | Sep 23, 2021 | Podcasts

SWGR 581 | Winning Team Strategies


How can you have an incredible team that works together and is committed to achieving organizational goals? Can you get your people to be in alignment with your vision, your mission and your goals? If you’re a team member, how can you help from within? As a two-time Olympian and National Basketball Coach of the Year, Sherry Winn knows teams from within and without. She is truly an expert at coaching leaders and team members to championship status. In this episode, she joins Elizabeth Bachman to discuss how you could create winning strategies for teams so you can succeed in the direction you want to go. If you want to know how you to deal with problems, handle conflicts with team members and help your team do better, then this episode is for you.

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Winning Strategies For Teams With Sherry Winn

Before we go into the meeting, I’d like to remind you that you can see how your presentation skills are going by taking our free four-minute assessment at That’s where you can see where your presentation skills are strong, and where perhaps a little support might get you better recognition and better results.

My guest is a leadership trainer and two-time Olympian, Sherry Winn. I had recorded an episode with Sherry for the show all about leadership. Once we hung up, I thought, “This woman was on an Olympic team twice. I need to ask her about teams,” so we did a follow-up interview. One of the things I love about Sherry is that she talks about how it’s all about the people, winning strategies, emotional intelligence and managing up. We talked about how to deal with someone who’s threatened by you and perhaps blocking you, how can you network strategically, and how can you always keep a perspective. There was so much wisdom in this conversation. Here’s the interview with Sherry Winn, Winning Strategies for Teams.

Sherry Winn is a two-time Olympian National Basketball Coach of the Year and Amazon three-time bestselling author. She’s an in-demand internationally renowned speaker who frequently speaks for up to 14,000 people at a time including companies such as StubHub, Anytime Fitness, New York Life, Edward Jones and Technicolor. With over 34 years of practicing leadership as a national championship basketball coach and a two-time Olympian, Sherry is an expert at coaching leaders and team members to championship status. She has successfully taken leaders beyond their levels of comfort to win against competitors who were superior in talent facilities and financial budgets. Through her win philosophy and winner principles, she shares insider secrets on how to succeed even when the odds seem insurmountable so that your team feels, act and conquers their goals like Olympians. Sherry, welcome back for this bonus episode.

I’m happy to be back, Elizabeth. I enjoy the last session with you. I’m thrilled to offer any insights and wisdom I might have for the people around you.

Last time, we talked a lot about leadership and the winning principles of leadership. Let’s do this from the point of view of leading teams but also being on teams. What can you talk about? How can you help teams to do better?

It’s all about people. That’s what people forget. When I first started coaching basketball, I called my father up and said, “What offense should I run?” I thought that was important. He said, “It doesn’t matter what offense you run. What matters is if you can get the people to run the offense.” That holds true in any business situation that you’re in. Can you get your people to be in alignment with your vision, mission and goals?

It's all about people. Take time and energy to get them in alignment. Share on X

This is a people issue. What that means is, are you taking the time and the energy? Are you doing the things that you need to do to get your people in alignment? That’s more of what it is than anything. What that lies into is, “Are you listening to them? Are you creating value for them?” What people look at are engagement, retention and motivation. This is all about people issues and skills.

Thinking about people skills, that’s easy to say, but where could one start? How do you get yourself to truly listen?

This comes with emotional intelligence. When I coach CEOs and C-Suite members, the first place we start with and the place that we’re always centered on is emotional intelligence. What does that bring to the table with that self-awareness? If you don’t have self-awareness, your ego runs the show. It’s impossible to listen to anybody else if your ego is running the show. That becomes, am I listening to you? Am I giving value to you? How am I being present with you?

I was talking to the former CEO of FedEx. One of the things he told me is a great story. He was talking about how he had to listen to himself in terms of, “Shut up. Listen to that person. Give them value. Think about it. Don’t let your ego run the show. My first inclination was to say, ‘I’m right. I’ve got this. Who are you to tell me?’ I was able to quieten that and able to come back and say, ‘Tell me more about that.’” You can get all the tips about listening in the world but if you can’t control that ego, the listening tips don’t matter.

Let’s talk about managing up. As a team member, what can you do for a manager who’s not listening?

That comes back to assertive communication skills. You have to focus on your controllable factors because you can’t say to your manager who’s not a good listener, “You need to listen.” That’s not going to work. You have to learn those assertive communication skills that enable you to learn how to say things the right way. Let’s say that you don’t feel like your manager is listening. Instead of telling your manager, “You’re not listening,” you say something like, “Walk me through the process of how you work with other people. I love to learn how you work with other people. Let’s talk about that. Show me how you do it.”

SWGR 581 | Winning Team Strategies

Winning Team Strategies: When you listen to your team, they see it as engagement, retention, and motivation.


What you’re allowing the person to do is to think about how they do it and then you could question them simply. You’re not going to throw it in their face. You can say, “That’s interesting. This is the way I do it. Can you explain to me how your way is better? Can you show me that way?” What you’re doing is giving them the opportunity to reflect upon something rather than throw it in their face. Managing up is not throwing something in their face. It means learning the skills to have a conversation where somebody doesn’t feel so defensive.

What do you do if someone’s being threatened by you? You got the feeling that they’re worried that you’re going to take their job. A lot of people have the whole zero-sum thinking like, “If one person succeeds, that means that I lose.” How can you deal with a manager who is determined not to let you succeed?

That’s tough. In that situation, the first thing is to say to the person, “I understand.” I love the word understand because it’s the bridge between you and somebody else, “I understand that your position is very important to you and you’re good at your position. I can understand why you value this position. I’m not here to take your position. I’m here to enhance you. As a valuable team member, I’m here to bring you up and not to bring you down. In what ways can we work together?”

Are there ways of going outside and around or building your network that is outside of the direct chain of command?

I wish that everybody was reasonable. That’s the key. If everybody were reasonable, it’d be so easy. The truth is they’re not. Why? Let’s go back to that self-awareness loop where people haven’t worked the zero-sum thinking. That’s the lack of awareness and emotional intelligence. You’re going to meet and deal with people who don’t have that.

What I always say is first, it’s that direct approach but if they’re not willing, you have to move on. You can’t just sit there and let somebody else determine where you’re going to move. You don’t run around somebody and go, “This person was not letting me do this.” That’s the wrong way. The right way is to show your brilliance, work ethic, worth to people and networking.

That means that in meetings and when opportunities arise to get on a committee, you’re constantly raising your hand. You’re like, “I’ll do this.” You’re showing them your skills and your abilities through that. It’s not like never. I don’t think it’s the right way to ever point out somebody else’s weaknesses but to point out your strengths, do the things you do well, and build those relationships so that other people see and hear you. It’s a process.

Can we buy one of your books and get some of this? This is a huge topic. Where could one start with one of your books about this?

Listen to your people, give them attention, and create value for them. Share on X

You can always go to my website You can email me there. You can see the books that I have and then go to Amazon. Also one of the things that I’m writing is a book I’m excited about, which is Winning Leadership: Seven Secrets for Employee Champions and Sales Superstars where I’ve interviewed almost 200 people, top CEOs, COOs, C-Suite execs. I’ve heard what they have to say about this.

These are not just my ideas. I’ve gotten some great insight from those folks who have dealt with this for years and decades. You can wait for that book. It was at my editor. We’re doing revisions. We’re back and forth. I can’t have an exact date but you can certainly email me and say, “When this comes out, I want this book.” It’s going to be full of tips, tools and techniques from folks like Beth Ford, who is the CEO of Land O’Lakes, a Fortune 500 company, as well as some other brilliant folks.

I work a lot with leaders and helping dealing with teams. There are a lot of things that come up where I’m always curious to get another expert’s insights on it. In terms of networking, one of the things that I noticed is that women tend to network sideways with people that they’re comfortable with. Men are often trying to network a couple of levels up. That is often how you rise in a company, how you get promoted. Do you have any tips for how to reach beyond your comfort zone, not be too pushy but make the connections?

It’s a truth that as women, our biggest tendency is we have low self-images. We’re insecure. It’s easier for us to reach across and to reach up, while men always think above themselves. It’s amazing how men are like, “On the resume, I’m not qualified for this job. I know I’m not but I’m going to go for it. They should choose me.” That’s a man’s mentality.

We’re socialized that way. We’re trained that way as children.

A woman is like, “I’m not qualified. Therefore, I cannot apply.” We put ourselves under the table more than we lift ourselves up. The biggest key to me is that continued awareness that as you grow your emotional intelligence and as you grow you, you understand that we’re all worthy. This is the thing that people don’t get but I think that anybody I meet, I don’t care about their title. I care about who they are.

I have that mentality like, “Who are you? I want to know who you are personally.” That’s more important to me than any title. As you reach out there to people and you start talking to people, remember that they are people. The number of people that I’ve talked to, you’d think, “They’re perfect. They got it all together.” When you start talking to them, you discovered they were depressed once or are still fighting. They are over-eaters, smoke and gamble too much or have trouble with their relationship. They are people.

At the end of the day, they may have success in one area of their life but they are still people. If you can remember that whoever you talked to is a person and as a human, we have those challenges. You might be an expert in the field that they’re not. Your relationship at home might be incredibly beautiful, something that they would die for. Put it in perspective as you’re talking to people. Remember, they are people or human beings. They all have their struggles.

Do you have any suggestions for how we could reach out for a skip-level conversation? How do we find the mentors who could get us where we want to go, especially if there’s someone who’s blocking?

There’s you. You and I do that. There are some people out there.

They’re mentoring people for years.

SWGR 581 | Winning Team Strategies

Winning Team Strategies: Have a direct approach, but if they’re not willing, you have to move on.


If you’re a woman, I would look for a woman coach or mentor. What that looks like is somebody who you feel has done it and has those conversations and networks, and somebody who you feel comfortable with. There are tons of coaches that you can find. The difference is, are they real? Did they just say something? Have they done the work? You’re going to reach out to those kinds of folks. To me, anybody who’s ever successful is going to be uncomfortable with the next move. We all are.

The difference between those folks, as you know Elizabeth, that you’ve worked with is you feel the fear and do it anyway. You recognize it’s a fear and a thing that’s preventing you from the next step but you do it anyway. You’re like, “This is fear. I’m reaching out of my comfort zone. I’m going to take this step anyway.” That’s the difference between the people who are successful and those who are not. For me, it always goes back to internal work.

If you have done the internal work, you will take the next step. If you haven’t, you’re going to let your fear block you. You’re looking for networks and people. Join networks and people. Go to mastermind groups and get a code. Read those books and do your daily work every single day that allows you to be the person you want to be. If you’re going to reach out, you first have to fill your cup. You have to fill yourself up before you can take the next step.

I’m thinking about within an organization. How do you reach out to the people who can sponsor you and help you within an organization? First, they have to know that you’re there and you exist.

You ask somebody above you to mentor you. I would say to somebody, “I’ve admired you from afar. Here are the things that I see that you do. I want to know how you do these things. Would you mind mentoring me an hour a week? Would you mind if I pick your brain every once in a while? I’ll take you to lunch. I will buy your lunch. I’d love to take you to lunch.”

Ask them if you can gain insight. When you do ask them out, don’t try to prove how brilliant you are. Don’t talk about yourself. Ask them deep questions. The better question that you’ll ask, the better answer you’ll get. What they’re going to notice is your willingness to be coached and learn. You’re giving attention to them and building a relationship.

Don’t go to lunch and go, “I did this and that.” No. You build a relationship. As you build the relationship, you let little things slip through the things that you’ve accomplished and done. You would say, “Here’s something that I came across. I want you to know this is what I did. What would you have done differently?” You’re going to show your brilliance there. They’ll go, “That was great. You were remarkable.” You didn’t say, “I was great.” You didn’t go in barging like that. Through those conversations where you’re building relationships, people will notice you.

A man can brag but a woman can’t. It’s a cultural expectation. People get turned off when women brag but you can drop hints about what you’ve done. Another thing I find often with my clients is they are so careful about crediting the team often that they have forgotten to say, “I ran this project. I did this idea.” There’s a balance. It is a tight rope that powerful women walk showing how good you are and mentioning that it’s crediting the team but also saying, “This was my baby and I ran this project.”

You don’t want to get lost when you’re complimenting your team. You can’t do it all with them. What you’re saying is so brilliant. Your insights about women are true because we’re so much about nurturing, compassion and being in collaboration. Those are the things that women do.

Women are good at it and it’s a great asset to your team.

It's impossible to listen to anybody else if your ego is running the show. Share on X

These are the things that I’ve learned. This is a moment that I got the big a-ha. I was attending an event. I was with the VIP group who got to meet these special people. I was standing in a group of about six people and we were all introducing ourselves to this guy. He’s a multimillionaire who had written a book and running a company.

Everybody wants to know him and introducing themselves. He comes to me and I said, “I’m Sherry Winn. It’s so nice to meet you.” My friend goes, “Tell him who you are.” I was like, “I’m a two-time Olympian.” The moment that I gave myself credit for something, he forgot everybody else in the room like it was just the two of us having a conversation.

He brushed everybody else off and he wanted to know about me. You have to let people know who you are. I’m not kidding you. We had a one-on-one for about 45 minutes. He wants to know all about me. I thought, “I’m missing the boat here.” People need to know what I’ve accomplished because that gets you the conversation. You’re not bragging.

There’s a difference between being confident and bragging. It’s a matter of fact. I was a two-time Olympian and I get to own that because I did it. If I’m shoving it in my face all the time, that’s different but if somebody says to me, “Look at your rank. Were you an Olympian?” I go, “Yeah, I was.” They’ll say, “When?” I’ll go, “1984 and 1988.” I can’t just drop it unless they want to know more. The difference between that is somebody who’s arrogant or insecure and goes, “I was an Olympian. Do you know what I knew? Do you know where I went? Do you know who I talked to?” You start unloading on them. It tells the difference. If you share those things you’ve done, it’s okay to know that and to be that.

I’m doing the presentation skills training and the career training. I help people show up in a strong way, which is all that I learned from 30 years directing operas, running a small company, and playing with the big guys or the big folks. I leverage my experience of 30 years in international opera, directing people like Luciano Pavarotti, to help experts and women, especially, to truly be heard because it’s all about who you are and how you show up. It’s just dropping that in.

For those of you who are wondering how to do this, feel free to reach out to me or to Sherry. I had lots of versions of that before I figured out a way to say it in a way that I felt comfortable that gave me the credits that I directed hopper around the world and I ran a company but it’s not what I’m doing now. I’m working with a whole different public the way you do. We’re both using what we did in another totally different realm to leverage those skills.

I’m going to brag. I’m good on stage. I had that connection on how to connect with people on stage. I’ve never been afraid. Everybody goes, “Were you ever scared to speak?” I’m like, “Never. Not once.” I was doing these events. I’d walk off and I’d never get a gig from the event. I’m like, “I know I’m good. People are telling me I’m good.” People don’t go out of their way to say, “That was amazing.” They would just walk off. I said, “I’m not getting a gig from the gigs. This is making me upset.”

I was taught like, “You have to teach people while you’re on stage and how brilliant you are.” It’s there where you tell these stories and you let people know your brilliance. It’s the way you do it. It’s a very easy way. It’s filtered into the story. It doesn’t even feel like you’re bragging. It just stands out. When I started to do that, what I learned was I was getting gigs from gigs. Before that, I was getting a single gig and nothing from the gig. This is very important that you learn that.

Another thing, this works with speaking gigs but it works inside the company too. If you make a connection, then ask for the next one, “Who else should I talk to? Would you be so kind to do an introduction?” That’s what we forget to ask. I’m trying to make myself ask more. Even me, there’s something I teach to my clients and forget to do myself.

It’s better if it comes from somebody else. I call it third-party endorsement in the marketing world. You have to talk about how to have someone else say, “I had this amazing conversation with Sherry Winn. You need to know her.” Let me ask you one more thing. Speaking of leveraging experience from a totally different background, can you think of things you learned as a team member or maybe as a team member watching your own coaches that you’re using now? It’s probably stuff that’s automatic.

SWGR 581 | Winning Team Strategies

Winning Team Strategies: You have to teach people while you’re on stage, how brilliant you are, you have to. It doesn’t even feel like you’re bragging. It just stands out.


What we forget as team members that’s big is, “How can I serve, support and grow you? What can I do to help you get what you want?” A lot of times it comes with zero-sum thinking. A lot of people call it living in lack. The more people you help get what they want, the more you’ll get what you want. As a team member, the most important thing is to forget about you, you, you and me, me, me.

If you are playing basketball and you’re the point guard, you’d say to your post player, “I know how to get you more points. On the court, everybody wants more points and I will give you more points. Do this. I can guarantee you. I’ll get the ball more to you.” You’re giving them what they want. By doing that by reaching out to folk or to anybody, when you’re thinking about, “How can I support and serve you,” people will do business and work more with people they know, like and trust.

I found this out early in my basketball career, which is funny. This is back in the ’70s or ’80s. I’m on the court. There’s a division between the White girls and the Black girls. I had this massive blow-up when we’re in the gym playing with ourselves one day with one of my Black teammates. She says, “You never pass the ball to us. You don’t think we can play.” I went to them the next day. I said, “I am so sorry. Dana, I did not realize I was doing that. I will make every effort to make sure that you guys get the ball as much if not more.”

The next five days are like, “Anybody else on the team that’s Black. I’m going to pass the ball to you.” What happened is she and I developed such a team or a tandem that we fed off each other. We played so well together. We became this incredible machine that other teams couldn’t stop. It was me realizing that I needed to reach out to her. I didn’t agree with what she said. I was like, “I could have stood there and fought it. That’s not true. I treat everybody fairly,” but I didn’t. I said, “What does she need to hear and see so that we can work together.” That’s the important thing.

I could have fought to be right. In my mind, I was right. I thought I was distributing the ball equally but that’s not what her perception was. When I went over and met her in that direction, we developed an incredible team and tandem working together. It’s your ability first, the ego thing that jumps up in your throat that you want to say, “I’m right.” You have to tamp that down and say, “What do you need? What do you see? How can I support?”

Met the other person to be right. Sometimes I would say, “We’ll do it your way.” Inside, I was like, “I’m still right.” I’ve learned how to shut my mouth. I might still think I’m right but that’s the thing. I’m the oldest child so I’m used to telling people what to do. All my little sisters would say, “You always think you’re right.”

It’s a tough thing to do. As a national championship basketball coach, the way that I won games was not being right. The way I won games is to ask my players, “What do you think we should do? What play should we run? What do you guys feel most comfortable doing here?” Sometimes they had no answer but a lot of times I’d say, “Let’s do this.” It’s listening to them, hearing what they needed, wanted and felt, rather than me saying, “I have to draft it because I’m the coach.” Once I learned that, it made a huge difference. It’s not my team. It’s their team.

Thank you so much for coming back. I’m so excited. I get to post this as a bonus episode. We get to promote you twice. I’m delighted to have had you here. For those of you who are reading, if you are curious about how your presentation skills are doing, you could take our free four-minute assessment at You can see where your presentation skills are strong and where you might need a little support to get you the results that you’re looking for. Sherry, thank you so much for coming back. It’s been an honor to have you on the show.

Elizabeth, I appreciate you, what you do, how you reach out to other people, the things that you do to help women become the best they can be, to help people understand why women get stuck and helping them move forward. Thank you so much. It’s been an honor to talk to you twice.

Thank you, everybody. I’ll see you in the next episode.


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About Sherry Winn

SWGR 581 | Winning Team StrategiesSherry Winn Is a Two-Time Olympian, National Basketball Coach of The Year, and Amazon Three-Time Best Selling Author. She is an in-demand internationally renowned speaker who frequently speaks for up to 14,000 people at a time including companies such as StubHub, AnyTime Fitness, New York Life, Edward Jones, and Technicolor.
With over 34 years of practicing leadership as a National Championship Basketball Coach and a Two-Time Olympian, Sherry is an expert at coaching leaders and team members to championship status. She has successfully taken leaders beyond their levels of comfort to “WIN” against competitors who were superior in talent, facilities, and financial budgets. Through her WIN Philosophy ™ and WINNER Principles ™, she shares insider secrets on how to succeed even when the odds seem insurmountable so that your team feels, acts, and conquers their goals like Olympians.