CNN once called Molly Fletcher “the female Jerry Maguire” due to the fact that she recruited and represented hundreds of sport’s biggest names as their agent. She’s been featured by ESPN, Fast Company, Forbes, and Sports Illustrated. She’s the author of five books, including A Winner’s Guide to Negotiating and The Business of Being the Best. As the CEO of the Molly Fletcher Company, she delivers keynote speeches, offers leadership training, and negotiation training.

In our interview with Molly on The Learn to Lead Podcast, we had the pleasure of discussing with Molly the challenges and triumphs of being a woman who leads in a male-dominated industry, the lessons she learned from peak performers in the world of sports, and how she’s been able to translate those lessons for readers and clients in the years since she has become an in-demand speaker on the topic of leadership.

The Interview

Thanks so much for joining us today, Molly. I want to start with one of the largest transitions that you made in your career. You spent over 14 years as the President of Client Representation at CSE, as one of the only female sports agents in the industry. Then you made the move to found your own company. What was the most impactful thing that you learned about yourself as a leader during that transitional period?

Well, it was interesting. I learned that you’ve got to trust your gut and you’ve got to follow your heart. If you’re closing a gap in the market and you’re following your heart, then it’s probably going to work. For me, the transition was super organic. I’d written a couple of books and companies started asking me to speak and I started doing that just for fun and found the message was resonating and connecting and helping people. The calls kept coming in to a point that I had to make a decision.

I really felt like I was able to use a God-given gift of speaking and sharing this unique platform that I had as an agent for so long. It was helping resonate with business people. It was a really organic transition, a natural transition, and certainly, one that candidly, I wish I might’ve started just a smidge earlier. It’s been so fun.

Let’s go back a little bit to your origin story. I hit on it a little bit in the introduction, but when did you first know that the world of being a sports agent was something that both interested you and was one for which you had the skills to succeed?

Well, I moved down to Atlanta from Michigan with about $2,000 to find a job in sports and didn’t have one when I got down to Atlanta. The Super Bowl was coming to Atlanta, the Olympics, there was a bunch of stuff coming. I felt like it was a good spot to go, I had a high school friend living in Atlanta and she said I could stay with her for free until I found a job.

I was just doing a lot of informational interviews, asking a lot of people for advice. When you ask for advice, you get a job, and when you ask for a job, you get advice. I was doing that and building quite a network of people that were really kind to give me advice.

As I kept down that journey, I think I learned one of the most important things for us as human beings is curiosity. I tried to be curious inside of that process and really learn from people who were a little bit ahead of me.

When I realized it was something that I could help athletes and coaches with, and something that I was potentially good at, was when I recognized these are people who just happen to be really, really good at something, throwing a baseball, coaching, whatever it might be. I authentically wanted to help them maximize a really unique window of time.

What these guys and girls do inside of 5 or 10 years is remarkably unique and you can’t get it back. It’s so special. They’ve got to maximize it.

I realized that I could connect with them authentically, serve them, and, as a female, have a unique edge. I looked at them, I think, a little bit more holistically. It wasn’t to me just about the contract. Certainly, we didn’t want to leave money on the table. We wanted to get great deals, no question about it, and we did, but I also saw an opportunity to represent a whole family.

It’s a lot easier for Matt Kuchar to stand over a put on Sunday and drain it when his personal life is intact. It’s a lot easier for Izzo to walk out and coach a game when his world is intact.

I took a little bit of a different approach and built a team around that so that we could serve our clients, not just as it relates to the work that they do, but, in all the things that contribute to their ability to execute on the court or the course, or the field.

It’s really fascinating. Do you have advice for your younger self, or somebody earlier on in their career, what you wish you maybe would have known, leadership training you wish you’d had, or what you wish you would have spent more time on, or worried about less?

I think my biggest advice is to go for it, to be curious, to be a little bit fearless, to go for what you want. Any competitive industry, it’s going to be tough, and there’s going to be roadblocks, you’re going to have to put in a lot of work, and a lot of time. You’re going to have to get creative, and all those things, but want it, regardless of the “No’s” that you’ll get along the way.

There was thousands of people that were like, “Molly, there are not female baseball agents. You didn’t play, what are you thinking?” I really just ignored all of that, because I wanted it and felt confident as I got into it more that I could contribute, particularly where I really started in baseball.

My advice is: stay fearless, believe in what you want enough that when you hit the roadblocks, you keep going. If you want it bad enough, that passion, that purpose, will suffocate that fear. It will drive right over those speed bumps.

One of the things that you’ve hit on, on a few occasions, is how many different clients you had, or how many different responsibilities that you had in a given day, or a given week. What are some tangible ways to ensure that anyone can set those effective boundaries, and ensure that you’re hitting the peak performance that is necessary to succeed in any industry?

Well, I think you’ve got to know clearly what you want most, what really matters most, what matters most for you to win. That was interesting for me, as an agent.

I came from a world where athletes manage their energy more than they manage their time because what matters most isn’t that they show up to the field per se, at 2:00 or 2:30 or 3:00. What matters is that they show up physically, emotionally, mentally ready to go. It’s not enough for Brady to get to the field, what matters is, Is he was ready to deliver? Business people, I think, generally, look at life through the lens of their calendar, through time.

For me, when we think about delivering results, when we think about making an impact, you’ve got to get really clear on what matters most, in order for you to do that. Then have the discipline to say yes or no, because I don’t think we can lead, we can solve, we can serve, we can sell, we can inspire if we don’t have enough energy. We have to be able to pour from a full cup.

My husband and I have three children, and we had three in 12 months, which is hard to do, but we had one and then we had twins. People say, “How did that work as a female with kids and travelling, and all that?” To me, it was about getting really clear on what mattered most, and then having the discipline and intentionality to say yes or no. I think that’s an important thing for great leaders, aspiring leaders to be able to do.

One of your focus areas is specifically on negotiation, which has implications not just in the world that you operated in, but it has implications in all aspects of life. When you personally were preparing for a negotiation, what did that prep look like, or what are the things that we should be thinking about before we walk into a negotiation?

Preparation, of course, is imperative. We have a course called Game Changer Negotiation Training and we teach negotiation. I certainly was inside of a lot of those kinds of conversations, and to me, that’s what negotiation is. It’s really just a conversation. It’s a difficult one at times, but it’s a conversation. We want to be prepared in a lot of ways.

I think one of the mistakes people make when they negotiate is they spend a whole lot of time worrying about what they want. I actually think you should spend a ton of time worrying about what matters most to the other person, really get in their head, get in their heart. What are they worried about? What do they need? What gap are you really closing for them? All of that, in my opinion, drives connection. To me, negotiation is a conversation and in order to have a conversation, you at some level need to have a bit of a relationship.

I found in negotiating half a billion in deals that the better the relationship, the better the outcome, and the better the quality of the deal. In fact, the better the relationship, often, I could close deals a little bit quicker. As we know, as leaders, if we can get our salespeople closing deals faster, that can be a powerful thing.

People would think, “Oh yes, you take the gloves off, you get on the other side of the table, man, and you just go.” To me, that’s not what it’s about. I think in order to close great deals, close them again and again and again, if you want to be a transactional negotiator, then sure that might work. But if you want to ever go back to that relationship, to that individual company or whatever it might be, we’ve got to build great relationships. I think relationships are the foundation of great negotiations.

What are you looking for in the people that work for you and when those individuals are ascending up the organization or they’re getting more and more responsibilities from you and from others, what are the key skills that you notice right away or that you’re looking to cultivate in future leaders?

I feel really blessed. I have an incredible team who’s been with me a long time and I’m so grateful for that. The people that we look to add are people who believe in our mission and they’re truly connected to it, not just in their head, but in their heart. They are people that are curious about what’s possible. They’re not afraid to push the envelope. They’re not afraid to push back on me. I love that. They’re insatiably curious.

They’re clear, too, about what they’re good at and what they’re not good at, and they’re not afraid to raise their hand and say, “I need help. This isn’t really what I’m good at.”

I like to put people in roles that they can thrive using their gifts, but also pushing them a little bit to get uncomfortable in a way that takes them on a journey as a leader to where they want to go.

I look for people who have discipline. There are times when you’ve got to roll your sleeves up and grind it a bit. In order to do that, you’ve got to have some discipline, you’ve got to be able to put in the work.

Those are just a couple of things that come up for me that we look for and then I would say too, over all of that, it’s someone with great energy. Somebody that has a lot of energy and focus toward our mission and the energy to put toward that mission.

When you look at the arc of your leadership journey, what surprises you the most about how you’ve changed? And what are you most proud of in terms of how you’ve evolved as a leader?

What surprised me maybe is: it’s hard. It’s really hard being a leader and that’s why I have a coach because I lean on him to support me. That’s why I have a network of people that I can lean on. An amazing husband. You need people with absolutely no agenda but to help you grow as a leader so that you can get better. Somebody that isn’t afraid to show your blind spots, show your gaps because I certainly have plenty. We all do. That would be something that surprised me.

I’m proud of my vulnerability to my team at times, because I think they need to know that you need them and that their advice and support is an important part of the organization’s ability to grow. I’m a proponent and fan of Brené Brown’s work on vulnerability as courage. I think there is nothing more important now.

As a leader, you absolutely have to put the stake in the ground at times and make really tough decisions, but I’m not afraid along the way before I do that to be really curious, to be a little bit vulnerable at times and ask my team questions that might uncover things that I haven’t thought about.

As I said earlier, curiosity. One of the most powerful things that we can do as leaders is listen. I remember sitting with a woman who was a bit of a mentor for me years ago, and she started a company in a business vertical that she really knew very little about and I said, “What are you doing? How are you going to do this?” She said “Listen. I’m going to listen. I’m going to put really smart people around me that are good at what they do as it relates to the core business needs that we have, then I’m going to listen. I’m going to ask great questions and then I’m going to trust them.” Boy, that was a powerful lesson for me and I try to emulate that too.

Before we shift to the final two questions, you’ve hit on a few of the people that you worked with: Hall of Fame Pitcher John Smoltz, PGA tour golfer Matt Koocher, broadcaster Erin Andrews, coaches Tom Izzo and Doc Rivers. Some incredibly well-known individuals. If I forced you to distill all that time spent working side by side with some of them to one to two things that you learned about successful leadership, what would you say some of those recurring lessons were?

Wow, there are so many. I feel so fortunate and blessed that I really had a front-row seat to peak performance for almost two decades because when you’re around these guys and girls for so long, you watch the way they behave and prepare and recover and lead and solve and serve. What I saw the best do is be curious, and they’re not afraid to be vulnerable.

Tom Izzo will pick up the phone and call a softball coach at the University of Michigan and ask her questions because she’s a heck of a coach. Geno Auriemma, on my podcast said, “Complacency is the enemy of success.” The best are always trying to get a little bit better and they’re not afraid to ask questions of others so that they can learn.

I said to Geno, “Geno, you’ve won 11 national championships. You’ve won over a thousand basketball games with different athletes against different teams. People have stayed healthy. How have you done it?” He said, “I’m always curious. I’m always trying to get better.” That’s something that I see and continue to see consistently in all of these remarkable people.

Well, that is a wonderful spot to shift to the final questions that we ask all of our guests and the first one is this if could describe your personal leadership style, but I only gave you one word, what would that word be?

I’m not very good at following the rules Matthew, maybe you figured that out, but I would say authentically curious. If you made me say one, I’d probably say curious.

I like it. The final rapid-fire question is this: What is the best piece of advice that you have ever received?

It was from Dabo Swinney and, I think this was cool for your listeners, Dabo said, “Serve their heart, not their talent.” I love that. I’ve received a ton of amazing advice, but that’s the one that comes up for me right now. Dabo says when he thinks about his athletes, “Serve their heart, not their talent.”

Wow, that’s a powerful thing, because it’s easy as leaders to get caught up in the things that the people that work for you do to drive the organization forward, but it’s also important to recognize who they are and what they want most and their own journeys to continue to grow in their careers.

You can learn more about Molly and her work with leaders on her website.

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This interview has been edited for clarity.