Molly Fletcher: The Internal Negotiation Behind Every Success
13 Mar 2025 · 29 min
Podcast episode (March 2025) of Negotiate Anything featuring Molly Fletcher, former sports agent, author, and speaker. Molly traces how early modeling (her mother), athletics (tennis), and creative value‑adding (teaching tennis while living in an apartment complex) developed her negotiation instincts. She emphasizes practicing small, safe negotiations to build confidence, centering the other party to create connection and common ground, and treating negotiation as a life philosophy she calls Dynamic Drive. Molly also discusses overcoming gender bias in a male‑dominated sports business, offers concrete anecdotes (e.g., paying up front for three children’s braces to simplify billing), and plugs her upcoming book Dynamic Drive (release Sept 3) and GetDynamicDrive.com for resources.
Questions this episode answers
September 3 (year stated as forthcoming in the transcript).
$2,000.
Nine years.
GetDynamicDrive.com.
Hey, I'm Kwame Christian, and you are about to step into the world of Negotiate Anything, the number one negotiation podcast in the world, where we teach you how to make difficult conversations easier while getting more of what you want in the process. Each episode is packed with practical tips and strategies from the experts. We delve into negotiation, conflict resolution, and leadership skills that are crucial in both business and in life. Whether you're closing a deal, managing a team, or navigating personal relationships, Negotiate Anything provides you with the tools you need to succeed. Our conversations are real, relatable, and most importantly, rooted in practicality. So if you're ready to transform your conversations and elevate your negotiation skills, join me on Negotiate Anything. Subscribe and listen on Apple Podcasts, Spotify, or wherever you love to listen. Let's make every conversation a winning negotiation. Molly, welcome to the show.
Thanks for having me. I am. I'm honored to be with you.
Yes, and we are honored to have you, my friend. So how would you get us started? By telling us a little bit about yourself and what you do.
Yeah, for sure. Well, let's see. I'm married to my wonderful husband of 26 years, Fred. We have three daughters, most importantly. And so for almost 20 years, I was a sports agent and represented incredible athletes, coaches, broadcasters, hall of Famers, Olympians, and then I wrote a couple books, and those did well. So, you know, I'm a former sports agent, now author of. I have a sixth book coming out September 3rd, Dynamic Drive. I speak and have a podcast like you, Game Changers with Molly Fletcher. So that's sort of a nutshell of where I am now.
That's incredible. I mean, you're winning on all levels. Sounds like you have a beautiful family, multiple books, 20 year career in being an agent. And welcome to the podcast and game. This is great. And so, of course, listeners, we're going to talk about this new book, Dynamic Drive, but we also need to address the fact that we have an expert deal maker and negotiator here today. So can you tell us a bit about how your negotiation skills have been able to translate into all of these different industries?
Yeah, absolutely. And I certainly love your show and I love talking about, as we talked about, the conversation of negotiation, which essentially is what it is, Right? It's a difficult conversation, certainly, but it's a conversation for me. I. It started really, when I was a kid. I would watch my mom. We would go to the grocery store and I'd watch her, you know, convince the checkout woman to take an old expired coupon and use it out of the kindness of her heart. Or I'd watch her, you know, try to get an exception for me to come watch a play with her. When I was 14 and the cutoff for the adult ticket was 14, and I had just turned 14, so I would watch her so often do that. And so I think at some level, I knew that it was safe, it was a conversation, and that if you approached it as a human being, understanding who and what you're having a conversation with and about in service of connection, that you can get a better outcome. And so I think I consumed that without even realizing it at some level. And then I got down to Atlanta from Michigan, where I, I grew up, to pursue a career in the sports business. And, you know, for me, I always have believed, and I think as a kid, watching even my mom, that if we can make the lives of the people that we want to do deals with, we want to connect with, we want to potentially, you know, close a gap with, if we can do it sort of with them in the center of it at some level versus us, we can often drive better outcomes. And so for me, you know, I, when I got down to Atlanta, for example, I had learned that there was a, an apartment complex that was going to need a tennis pro. I played tennis at Michigan State. And so, you know, I moved to Atlanta with 2,000 bucks, no job. I was sleeping on my friend's couch in her apartment until I could figure it out. And so I found out about this apartment that, that needed a tennis pro. And tennis is a big deal in Atlanta. So long and short of that story is I began to add value to manager. I, I, I brought her tennis tips to put in the newsletter. I'd gotten my buddy at Wilson Sporting Goods to send me stuff that, that I could give away if I had the opportunity to be the tennis pro there. I got this pizza place across the street to give me free pizza for the people that came to my clinics. And the, the, the long story short is that I lived in that apartment complex, taught tennis for, for, for nine years. And, and the story is super fun. I share it in a TED talk that I gave a few years ago. But, you know, at the most fundamental level, right, that was huge because I was able to remove what is often a very large expense for all of us, which is housing. And then, you know, I progressed as I stepped into the role as, as a sports agent. I mean, I, I would say, you know, I negotiated free pizza and tennis tips and free gear from Wilson Right. But then when I got into the sort of the business world, it started really with little things like getting a trade out for one of my NBA coaches or getting free sunglasses for a client. And then it progressed to getting an athlete to show up for an autograph signing at an opening of a CVS or a speaking engagement or another kind of appearance of some kind of. And then it progressed from there. When I had baseball players that as I progressed in my career who were arbitration eligible or free agents or college coaches or broadcaster deals would come up and I had evolved enough and really began to have the confidence, which I think is an important word to consider in this kind of conversation, to step into the bigger moments of multimillion dollar, multi year deals for the athletes and the coaches that I represented and the broadcasters, and then even for myself, to me, it's about getting the reps right. I think the more that we step into these kinds of conversations and the more that we, that we step into them in service of connection, in service of creating what I often talk about as common ground, and, you know, then we can start to close the gap and solve and serve the person that we're potentially doing a deal with. So I'll pause there. You can imagine, man, I've got stories, you know, left and right that I can unpack for you, but those are. That's just sort of the way that it evolved, I guess, at some level.
Amazing. And so, Molly, after what, eight years and 1300 episodes of the podcast, I think your life story is the most negotiate anything life story I've ever heard. This is incredible. So let me outline all of the things that I love and end off with the, with the big reveal here. So we have. First of all, this was modeled to you by your mother, mastering these everyday negotiations. And I think for the people who are listening, this helps us to recognize that if you have a family, you're not just negotiating for yourself to move yourself forward and advance your family, but you're also serving as a role model for your family to let them know that you can and should negotiate anything. And then you recognize that through your life, just from your upbringing there, and then as an adult, playing tennis, teaching those tennis lessons, and then negotiating just free rent. That's incredible. And a lot of times people would not even conceive that as a possibility. And we're oftentimes limited by our own imagination when it comes to negotiation. Not just the imagination, but also skills and confidence. But if we don't believe it, we can't achieve it. And Then the big reveal is tennis was my favorite sport. I was president of a club team. Yeah. At Ohio State, and we went to nationals. Billie Jean King watched the tournament and it was really cool. So I was not varsity level like you, but I tried my best. So I loved every element of this story. Molly, this was great.
That's awesome. That's cool. Wow, I love that. That's awesome. And Billie Jean King, I had a chance to do an event with her. What a neat lady and what she has done for the world and for the game of tennis.
Absolutely.
She's incredible. That's pretty cool.
Yes. And now let's talk about confidence, too. Let's talk about confidence because I love. I can see that sports mentality coming into this because you said you have to those reps. And by getting those reps at what others might consider to be a lower level, it gave you the confidence at a higher level. And here's the thing. When it. When from the outside looking in, we might see these everyday negotiations for coupons or whatever, it happens to be as lower level. But for us at that time, it is incredibly high level, incredibly high stakes. And as we start to negotiate up in our career now, we're putting ourselves in a position where we are used to advocating for ourselves in this way. So can you talk about the importance of confidence as it relates to actually putting negotiation skills into play?
Yeah, well, and you. And you bring up a good point. I mean, I think when we get the reps and when we step into the discomfort sometimes of asking for what we want, it doesn't, you know, it can be a little disconcerting. It's a little scary. We might get. No, and, but I think the more that we step into these moments, little ones, I mean. And to your point, you can practice. I mean, you know, if you go to Starbucks and get a coffee, you know, maybe just walk over to the barista and say, man, I forgot to. But, gosh, man, I'd love a shot of espresso in this. And I meant to add the red eye, but I, man, I forgot. I mean, do you have any, like, you know, a couple little, little extra espressos there that you could pop in here or I'm happy to go over and pay. I do that just for fun sometimes. And like a hundred percent of a hundred times they're like, oh, wait, no problem. And I'm not suggesting that we need to run around and be, you know, a mooch. Right. But what, but what I am saying is find little moments that are safe where you can practice, and. And then we build the confidence. And. And I think, you know, to. To your point about imagination, a minute ago, I'll tell you, it was funny. My husband and I have three girls, and when they were. I think they were like five, or maybe they were like six. Six and seven. That's a whole nother story. We had three kids in 12 months, but so they were. So they were like six. Six and Seven. And I take them to the orthodontist because they needed to get braces, or we thought that maybe they did. And so we go in, and it's right in the middle of. Of Atlanta. It's a really busy, great location. They have a great reputation. They've been around for a while, kind of. So we go in, they do the exam, and of course they're like, oh, yeah, all three of them. And I mean, it's like a landmine in there. They definitely need braces. So we. They said, you know, go back and sit with our manager in her office. She'll walk you through the plan and how it works and cost and all that.
That.
So we walk into her office and we sit down and she sort of opens up this file, and, you know, she goes, now here, you know, here's kind of the way, you know, the girls all need them. Shocker, right? That they all need the braces. I mean, that's just. Wow. They all need them. And she said, here's what the way it works. You know, we do phase one, which is, you know, a couple years, and then in a few years after phase one, we do phase two. And she said, so they're in phase one, so what we need to do is put braces on all of them. It takes a couple years. Come in every, you know, she walks me through it, and I said, okay, cool. And I said, so how does that, you know, work payment wise? And she said, well, essentially each girl is $3,000. And we just invoice you, and you pay, you know, monthly, quarterly, whatever you would like. And I remember sort of looking at. Her name was Renee. And I said, wow. I said, so, man. I mean, you guys are like. I mean, this. This place is happening. And she goes, oh, yeah. And I'm like, golly. I said, so, like, let me get this straight. Like, you have all these people, all these, you know, customers that come in, clients. I said, so all that place is packed, and I've been here for, you know, 45 minutes. I mean, is it like that all the time? She goes, all the time. It is humming in here. And I go, wow. She goes, well, we got two doctors. I mean, we serve. And she throws out a number. And I said, wow. And I go, so you, like, you are in charge of this? Like, you. You bill all of these people that roll through this door? She goes, yeah. And I go, wow. I mean, like, man. Like, do they all pay on time and stuff? I mean, what's that like? And she goes, heck, no, girl. No. And I go, and they got the braces on, so that's. You don't have a whole lot of leverage, right? And she kind of laughed, and I was sort of joking with her, and I go, wow. I said, so. So let me ask you this. I said, you know, you got to invoice these people. You got to chase them down. She's like, yes, it's a nightmare. It's how I spend half of my week. And I'm like, wow. And I said, well, what if we did something where, like, so three girls, nine grand over two years. What if I just paid you six grand up front? You know, like a buy two, get one free, and then you don't have to worry ever about invoicing me. I trust you. This is an incredible practice. What do you think? Like, you know, buy two get one free. And she just stared at me, and she goes, wow. Well, actually, you know, that's kind of interesting. She said, let me go ask the doctors. So she goes out and she comes back and she said, yeah, they love it. That's awesome. Perfect. I was like, sweet. So I share that only as a backdrop. That, like, that was a safe moment. You know what I mean? It's not like she's gonna kick me out of her office or tell me she doesn't want the business. So I share that only because I think, to your point about imagination. I love that you use that word, because that's what so much of this is about, is sort of looking for opportunities where everybody can win. Right? I mean, this is truly an example of a win win. And so I think it's about staying creative, looking for the opportunities big and small, to get the reps in a way that's comfortable for you, in a way that drives and aligns connection.
Hello, my friends. Before we get back to today's episode, I want to ask you a question. Have you ever wondered how to elevate your team's negotiation game and how you can help the folks on your team have better, difficult conversations? At the American Negotiation Institute, we offer transformative keynotes and workshops tailored to empower Professionals with top tier negotiation and conflict resolution skills. Whether it's a keynote for your next event or hands on training for your team, we've got you covered. Don't just negotiate. Master the art with the American Negotiation Institute. Click the link in the description to find out more. Elevate, negotiate and succeed. Yes. Oh, there's so much here. Because first we have that mentality where we're not assuming that this is a combative type of interaction. You are creating a true relationship, building rapport, empathizing, leading with curiosity, and then figuring out, like you said at the beginning, how can I make their lives better? And the beautiful thing about doing this and like you said, getting in the reps, is that you, number one, let's use some sports references here. Okay. You miss 100% of the shots you don't take, for example. Right. So we're not putting ourselves into, into winning position if we are afraid of negotiation. You have to actually have the conversation. That's the first thing. And what people don't fully appreciate going back to getting the reps in is that even if you don't get what you want, you still win because you're getting your reps in and you're getting better through the process. You're improving your skills. And at the same time, when you get that rejection, you're impro. Your resilience because you recognize that what happens after rejection, what happens after you hear no, life continues and you.
Right. Move forward. Yeah, nobody died.
Exactly. So empowering.
Well, you know, again, I mean, this book that I have coming out, Dynamic Drive, it is all about this consistent pursuit of better, of a better version of ourselves. This, this idea that the traditional definition of drive is one that is anchored in achievements, in an outcome. But what happens when you do that one, that thing that you're focused on? You, you, you train for a marathon, you run it, then you, you throw your spikes up. You know, you, you, you do, you know, you set a goal, you achieve it, and then you settle back into what I believe is the opposite of dynamic drive, which is complacency. So to your point, in, in, in these kinds of areas of our lives, like negotiation, like connection, curiosity, every day we have an opportunity to get the reps in and create and gain the confidence. And I think, you know, negotiation is messy. It's a zigzaggy line. There's unexpected things that happen. You're dealing with lots of different kind of people with different circumstances, personally and professionally. And so the more confidence we have in stepping into the discomfort, the Stretch zone, as I often call it. The more we get the reps and do that, the more that we'll see that we get stronger, we strengthen our confidence, which gives us the courage to step into the bigger moments and the bigger moments in service of not compromising our own worth ourselves. And you know, you can imagine, I mean, I'm a female. I was in a totally male dominated industry as a sports agent. When I stepped into the business, there was no women, none. So I was often the only woman in the room. And what I can tell you is there was lots and lots of moments where nobody would, even the general manager wouldn't even look at me. And, and so it was about the, the, the reps that I'd had gave me the courage in those moments of discomfort to embrace the discomfort, to go from defensiveness to curiosity. I often say to have the courage to pause when I needed to, to find ways to drive connection. As much as sometimes I gotta tell you, I mean, I'd want to come over the desk at the general manager and be like, dude, I am not his secretary or their attorney or whatever. You think I'm actually the player's agent. Like, as much as I'd want to come out and sort of do that, I'd look for an opportunity that felt authentic and real to create an opportunity to connect. Because that's, as we said earlier, that's what negotiation is all about. It's about connection. Because if, if we're going to get a deal done, we, we often have to have a conversation, we have to listen deeply, we have to be curious and, and when we're curious, we can unlock and listen to what their gaps are. I think that's one of the biggest mistakes people make is they, they walk into these moments, right? Even if it's personal or professional, and they think about, maybe somebody's listening that wants to negotiate a raise for themselves or for their team, or they negotiate mergers and acquisitions or they're negotiating with a vendor, whatever it might be. We often spend a whole lot of time thinking about what we're looking for. What do we want, what do we want, timing wise, financially, what are we going to view as a successful outcome? And I think that's a really big mistake. I mean, I think that those are all super important things to have in our, in our back pocket. But we've got to spend even more time knowing what matters most to the other side, right? When I would get ready to negotiate a contract for a free agent baseball player, I'd, I'd want To know if he was a middle infielder, I'd want to know where the team was with their, you know, overall salary outflows, you know, where, where, where are they relative to the minor league. What, what, what mental middle infielders are feeding up through the system, you know, who's on the free agent market. Also, all of the dynamic of the clubhouse. I mean, all of those things are in play and understanding. Because if we can get into the head and the heart of the person we're negotiating with, you know, I truly believe we, we can get better outcomes. And that's what I found. I mean, and ironically, right, because people think, oh man, sports agent, dude, you must have just, boom, take the gloves off, like, let's go. But what I found was I'd use words like we more than I. I'd get physically on the same side of the table as them whenever I could because I wanted it to be about connecting versus something that would be adversarial and, and drive.
Oh, Molly, there is so much in here. I feel like you should write at least six books.
I have a book on negotiat. I haven't even talked about that yet. Yeah, no, for sure. But yeah, it probably needs to be incredible.
And there's, there's so much to explore. But I want to focus in on just number one, the counterintuitive nature of negotiation. Where Hollywood creates this, these perceptions in us, and then our emotions will drive us to want to do the exact opposite of the right thing to do. And really, when it comes to being an expert high level negotiator, really what we have to do is fight what society might expect of us and also fight what internally we want to do because we're driven by our emotions in so many cases. And so you had to go through some of the negotiations that are toughest, not just in terms of dollar amount, not just in terms of how competitive the field was, but then also overcoming gender bias in that process. And so when you think about, for you, as you had to be resilient and strong going into these negotiations, what was it that allowed you to tap into that strength when it mattered most?
You know, I think it was knowing that the more that I stepped into the moments of discomfort, I became a better version of myself. I became a better negotiator. I became and created better outcomes for myself or for my clients. I began to, to recognize that obstacles are in fact opportunities for growth. That no is just feedback. It's not. No. That when we can step into the change, the Challenges the obstacles that the person that can come out the other side of those moments can become better, better leaders, better community members, better partners, better parents, better leaders. And so once I began to believe that this way of life, which I call dynamic drive, was in fact about stepping into what I call the stretch zone in the book. And the more that we do that, the stronger we get. And so it's like anything in our lives. When we start to do it and we see that there's a positive sort of return on that investment, if you will, then we inherently want to do more of it. And that's why I'm such a big proponent of people who are, you know, maybe listening and thinking, oh man, like I gotta tell you, like, she sort of sounds like she likes this, that's weird, or whatever they might be thinking. And what I would say to him is just, you know, step into the little moments, just a little, little ones, get the wraps in real life and the more you do that, the more comfortable you'll get in the bigger ones in service of the best version of you every single day.
I'm wondering how much your background as a high level athlete contributes to this resilient mentality. Is there, what kind of connection is there for you?
Yeah, I would say, you know, it's interesting that you say that. I would say it has served me really well and been helpful. And I say that in part because, but, but I would say for somebody listening, you know, I mean, it could be that you played the violin or the guitar or the piano, or you know, chess or fencing or what, or whatever it might be in life, or you just had two tough older brothers, I mean, who knows? But you know, for me, I think that as an athlete you have to get comfortable taking feedback. You have to get comfortable with trying new things and it not always working. You have to get comfortable with taking in feedback, be it that you've created yourself, you hit the ball into the bottom of the net or you know, or feedback from a coach and try new things. And so at some level as an athlete, you're constantly finding your space in a, or finding yourself in this place of discomfort. But what you also learn then is that you grow from that, you become better. You know, one of the stories I often tell, which as a tennis player you'd appreciate is I was going to walk onto the Michigan State tennis team and I went out on the court and to take a lesson from my coach and he said to me, because I was a super big time long shot to make that team at all. Like, I was. I started playing tennis when I was like, 13 or 14, wasn't nationally ranked. Yeah, I mean, I was started super late, right. Like, I. Because I played all these sports, which, by the way, is a whole nother topic, because I think it's important for kids to do that. But so I'm like 14. I walk out on the court and my coach says, look, I mean, you really want to make that team? And I said, I do. And he goes, molly, like, honestly, I've watched you just hang out at that baseline. It's like you're waiting for the point to develop. You're waiting for the ball to come to you. He's like, look, if you're going to make that team and have any shot other than carrying everybody's water bottles, he said, you got to get more aggressive. And I share that because he. We. We then played a game of sharks and minnows where he fed me balls, and it was about cutting off the angle, taking the ball on the rise, all of those things. But I tell that because it was really, at some level, one of the first moments that I realized that I had started to unintentionally settle, to get too comfortable back at the baseline, and that what I found was the more that I stepped in, the more that I caught off the angle, the more that I approached the net, took the ball on the rise, attacked, the better I got. And so I think that's sort of a metaphor for life, right? To. To step into lean and to cut off the angle, to. To take it on the rise. Right. And go for it. And. And we can become a better version of ourselves when we do that.
Molly, this is so good. And I could talk to you all day about this because I love the fact that we are blending the mindset. What's required in order for us to think differently about these scenarios, what we need to do in order to build our confidence so we could actually put our skills into action. And then you're tying this together with an overall life philosophy as well. Because I think that's where you really start to get disproportionate levels of return on investment here. When you start to look at negotiation not just as a tool of communication, not just as a problem solving tool, but also as a life philosophy that helps us to understand ourselves and others and move forward collaboratively, I think that's when we start to get those massive returns. So I really appreciate you breaking this down for us today, and I appreciate you again for writing all of these books. And the one we are here today to talk about is Dynamic Drive. So before you go, can you let the listeners know about your book, your podcast, and how they can get in touch?
Wow. Yeah. No, this was a super fun conversation and most importantly, hopeful that it's helping a lot of people step into more of these moments. Absolutely. People can learn a little bit more about the book. Get Dynamic Drive.com is the website. We have all kinds of bonuses. Two there for folks, leader guides, action guides, a bundle of videos, a myriad of things. It's just get dynamic drive.com and then my website is Molly Fletcher.
Amazing. Molly, thank you so much for joining us. Really appreciate it. Congratulations. You've just joined an elite club by listening to a full episode. You're now officially on the Negotiate Anything team. So welcome aboard. What most team members do is they subscribe to the podcast because that allows them to automatically get the latest episodes of the show. The best things in life lie on the other side of difficult conversations. Keep learning, keep practicing, and keep getting better. Your relationships will improve, your career will soar, and you'll have the confidence you need to get the most out of these crucial conversations. Again, thank you for joining the team. We're excited to have you, and I will see you in the next episode. I'll catch you later.