'You’ve Got To Push Past the Discomfort'

The silence lasted 90 seconds.

On one end of the phone was a Hall-of-Fame MLB general manager. On the other was Molly Fletcher, a young agent who had cut her teeth chauffeuring coaches around Atlanta and routinely showing up to college practices.

Now, she and the executive were in a tense standoff over potential arbitration for one of Fletcher’s top clients.

“I had already painted the picture of why we felt like our guy was deserving,” she said. “I didn’t need to fill that minute-and-a-half with, ‘Come on, man! Look at his stats.’”

Finally, the general manager interjected.

“Unbelievable,” he said. “You’ve got a deal, Molly. I’ll send over the terms sheet.”

Fletcher shares that story now in her work as a keynote speaker and best-selling author of six books as a critical lesson in the power in silence and the value of confidence in communication.

The Daily Coach spoke to her about breaking into the industry, key lessons from her countless negotiations with top sports executives, and what she hopes readers take from her new book, “Dynamic Drive.”

This interview has been edited and condensed for clarity.

Molly, thank you for doing this. Tell us about your childhood and some key lessons from your early years.

My mom was a speech pathologist in the public schools in Lansing, Mich. She loved it. She was really involved in the community and ran junior league and arts councils. My dad was a pharmaceutical sales rep. He was 6 a.m. until 3 or 4 in the afternoon begging doctors to take a meeting with him.

I learned a lot of sales stuff from my dad and relational components in life. From my mom, I learned so much about how important it is to immerse yourself in a community, to give back, and to be grateful for the things that we have.

You end up going to Michigan State and walking onto the tennis team. Can you share what your mom told you after your freshman year and why that was so important?

I was playing great tennis. I had rushed a sorority. I would go to class from time to time. When the report card came to the house — this was when they were mailed to your parents’ house — my mom opened it. I had a 1.8 cumulative GPA.

One of the classes, I had a D in, and I was sure I’d crushed the final. I picked up the phone and called the professor, “Sir, I think there’s been a mistake.” He paused and said, “I don’t know how to tell you this, but you were one point away from failing. You might want to hang up and be grateful for your D.”

I can still see the report card on the dining room table. My mom set it down and just said, “You can do better, Molly. You can be great.” That was it. That was the end of it. I got to work and got a 4.0 seven terms in a row and graduated with a 3.8.

I think it goes to one of the keys in my book: Resiliency. Fail, and fail often. In that case, I wasn’t necessarily pushing myself the right way, but I believe we’ve got to fail, recover, and not just come back to where we were, but come back above the water mark.

When did you decide you wanted to become an agent?

I went down to Atlanta (after graduating) with no job and $2,000. I was sleeping on the couch of a friend’s apartment.

I started networking. I answered the phones at the Super Bowl XXVIII host committee. It was a grind. I worked for a woman who was horrible, so mean. I would cry on my way home from work. But it was an opportunity to meet some incredible people in Atlanta who were sponsors.

I got an opportunity with a small agency that had a few clients and a few employees. I was hired for the Olympics to be a marketing coordinator driving (Team USA Basketball Coach) Lenny Wilkins around from one appearance to the next.

I remember thinking, “How are we going to get more clients?” I walked into our leader’s office with that same sort of fearlessness, probably a little bit of cluelessness, and said, “What’s our growth plan? What if we got more aggressive?”

How did you end up getting more clients?

Georgia Tech had an incredible baseball program. I literally just started going down to practices, leaning on the fence with scouts. I got to know the head coach — who was helpful — and parents and learned the language.

I remember once sitting in the stands with a parent saying, ”Tell me about the way these cleats work.” He said, “They’re spikes.” I was talking about a catcher and their glove. He goes, “It’s a mitt behind the plate, a glove in the field.” I learned it all and started signing baseball players. A baseball player recommended a golfer. College coaches at the time wanted to be NBA coaches. We started signing college coaches because we knew we could ladder them up to the NBA. It evolved organically.

I built a team around me of guys who had played at a high level at whatever sport it was and could have a different kind of conversation than I could.

That willingness to ask questions, even if they make you look a little naïve at times, isn’t always natural for people. Why were you comfortable doing that?

One of the keys I write about in “Dynamic Drive” is curiosity. I think curiosity creates chances for us. I grew up in an environment where you asked, you got an answer, and you dealt with the results. If my brothers were wrestling and I jumped into the middle of the pile, I was going to live with whatever happened inside of that pile, which was probably a bloody nose.

It was nurtured at some level to ask for what you want. It’s O.K. to ask questions. It’s O.K. to not know the answer. It’s O.K. to not be the smartest person in the room. It’s how you build better relationships.

When you ask people questions about themselves, you learn, you grow. I think it’s important for people to know there are such things as dumb questions. There are. But I think we want to ask the kinds of questions that can help us gain more respect because of the knowledge we’re able to demonstrate.

You’ve been in countless negotiations in your career. What are some steps leaders can take to negotiate more effectively?

Negotiation isn’t something we’re born with, but it’s something we can absolutely learn. I didn’t start negotiating $100 million contracts. I started negotiating to get them to move the cone for me to park Lenny Wilkins in front of the Dream Team practice facility.

One of my biggest pieces of advice to people is start getting reps. Practice in low-risk environments. That’s going to help you ladder up with the confidence you need in the bigger moments.

Negotiation is really just a difficult conversation. The more time we spend building relationships with the people we want to negotiate with and have better outcomes with, the better shot we have at creating and holding the space for the difficult conversations.

Were there common misconceptions you heard around your work?

As an agent, people think, “That’s crazy! You got on the other side of the table and took your gloves off. It was on!” But I found the stronger the relationship, the quicker I could get a deal done.

Is getting a little bit uncomfortable for a period of time worth the potential opportunity that it could create in my life and career? You’ve got to push past the discomfort into the space that allows you to ask and get what you deserve.

What other particularly memorable negotiations did you take part in during your career?

We negotiated Billy Donovan’s contract after he won back-to-back national championships at Florida to go to the Magic. Highest-paid guy in the NBA, does the deal, signs the contract, does the press conference, flies back the next day. “I’m out. I don’t want it.”

I tell that story often when I speak because I believe we were too transactional in our approach versus really asking him the difficult questions along the way in service of ensuring he was really clear.

He’s an incredible guy, super buttoned-up, sharp as can be. I think it’s always important — in service of the people we’re negotiating on behalf of — to have the courage to ask them the kinds of questions that will ensure there is a long-term outcome in service of what they want most.

You just wrote your sixth book, “Dynamic Drive.” What do you most want readers to take from it?

I began to see a common thread with high performers, whether they were a broadcaster, a coach, a basketball player, an NFL guy. But I also began to see something that concerned me. There are so many people who achieve remarkable success, but there are very few who actually find fulfillment.

What I realized is the secret isn’t just setting and reaching goals but aligning those goals with a deeper sense of meaning, of purpose, of what matters most.

“Drive” can sometimes get a bad rap. I think when people think about drive, they think set a goal and run hard toward it. It’s an outside-in approach to achievement. Dynamic drive is an inside-out approach. It’s continuous. There’s not a start and an end. You set goals but not in isolation of the person you’re becoming in that pursuit.

You write about this concept called the energy audit. Why is that so important?

Businesspeople are always obsessed with time and their calendars. In sports, great coaches and great athletes are obsessed with their energy.

When I came out of the agent business into a more traditional business environment, I thought this was so fascinating. People would show up at meetings and they’re mad they’re there. They go back-to-back-to-back and get to the meeting, the moment that really matters, and they’re not prepared because they don’t have the kind of energy to show up the way they want.

I promise you Serena, LeBron, Kobe, Brady are going to ensure they have the energy they need for the moments that matter… The audit is, what gives us energy, personally and professionally? What drains our energy, personally and professionally? What’s neutral?

We need to pull back and make sure we have the things that give us energy.

Q&A Resources

Molly Fletcher ― Website | Latest Book: Dynamic Drive | Speaking | X | Instagram | LinkedIn | YouTube | Facebook | TikTok

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