The ED’s 2025 Progressive Leader of the Year “Honors” Award Winner, Mike Dickinson, suggests that real leadership begins when you stop needing the spotlight.
(NOTE: This story was written by Mike Dickinson and appears in the November 2025 issue of ED Magazine.)
Stepping into leadership offers no blueprint, no manual for inspiring a team to follow. Leadership is messy, demanding, and if done right, transformational – a truth I learned the hard way. Early in my career, I thought being the best at my job made me a leader. If I could outwork, outthink, and outmaneuver the competition, that would automatically inspire others to do the same. But the truth: being great at your job makes you a performer, not necessarily a leader. Leadership is something else entirely.
I’ll be the first to admit, I made mistakes. My biggest one? I was a ‘ME’ player. Not a ‘WE’ player. I focused on my own numbers, my own wins, my own recognition. While that drive takes an individual far, it will take a team exactly nowhere.
My turning point came a few years ago when I joined The Pony and found the best mentor in the world: Jerry Westlund. Jerry showed me what true leadership looks like. He is someone I would run through a wall for. I remember thinking, ‘That’s the kind of leader I want to be; that’s the loyalty I want my team to feel.’
From that moment forward, my mission was clear: I had to stop being the star of the show and start building the kind of team that makes everyone a star.
Building a culture bigger than yourself
One of the first steps was creating a sense of belonging. More than clocking in and out, it’s about being part of something bigger. We call it Pony Nation for a reason; it’s not just a name, it’s a movement. When you can get people to buy into the idea that our success is collective, everything changes.
I tell my team: when one of us wins, all of us win. When one of us struggles, we all step up. It’s us against the world, not you alone against the world. TEAM: Together Everyone Achieves More. It sounds simple, but it’s powerful. People work harder when they know they’re fighting for something bigger than themselves.
Setting expectations & seeing potential
The next step was setting expectations. As a leader, you have to see greatness in people before they see it in themselves. When we bring someone onto the team, I tell them we’re looking for A-list players. And I mean it.
That doesn’t mean they’re perfect already. It means I can see their potential—what they could be in three years if they commit to growth. That’s a leader’s job: to envision what someone can become, then coach them step by step. I break it down into fundamentals, mastering the little things. Because 90% of success happens when nobody’s watching, if you do the ordinary with discipline, the extraordinary takes care of itself.
Putting people in the right position
Another lesson learned: talent without fit is wasted. Eagles aren’t meant to dive to the ocean floor, nor sharks to perch in trees. As a leader, you must truly know your people—their strengths, weaknesses and personalities. Then you place them in the proper position to win.
Once they’re in that spot, you let them operate. Give them space to learn, make mistakes, and grow. From a baseball background, I love the analogy of rookies who stumble before they shine. Most Hall of Famers weren’t legends in their first season. They struck out. They dropped the ball. They failed. But they kept going, and someone believed in them. That’s leadership: giving your people the room to become great.
“When you build your team around that philosophy, trading ‘ME’ for ‘WE’, you create something unstoppable. Leadership isn’t easy or glamorous. It’s not about titles or awards. It’s about the late nights, the tough conversations, failures turn into lessons, and the pride in your people’s success.”
— Mike Dickinson
Giving away the spotlight
Perhaps the most challenging part: as a leader, you have to step back from the limelight and give your team the credit they deserve. You brag about them louder than you brag about yourself. And when I watched Alex Wimberly win ED Magazine Employee of the Year, or saw Tori Morganstern nominated for a club award four years running, those were the proudest moments of my career. More rewarding than any recognition I could’ve gotten myself.
It also goes beyond the awards when I look at the growth of a Club Manager like Amanda St. Onge, who started as a bartender and is now one of the most consistent leaders on the team because that’s the objective measure of leadership: what your people achieve when you’ve set the stage for them to shine.
Encouraging innovation
Leadership isn’t about having all the answers, but about asking the right questions. I encourage my staff to think outside the box, to pitch ideas, and to take calculated risks. I want their creativity, not just compliance. That means sometimes they’ll swing and miss. But I’d rather have a team that’s swinging than one standing frozen at the plate.
Solving problems, leading by example
Every day as a leader is a problem-solving exercise. Big, minor, unexpected problems all find their way to you. The day they don’t is the day you’ve stopped being relevant.
So how do you handle it? With consistency. With a work ethic. By setting the example. Be the first one in the building. Answer the 4 a.m. email. Pick up the phone when no one else will. Keep producing ideas. Keep bringing people to the table. Never rest on yesterday’s win, because tomorrow is already knocking.
The secret ingredient
Ultimately, the secret to leadership is simple yet not easy: you must genuinely care about the people you lead. Not just their performance, but their lives as well. Not just what they bring to the team, but who they’re becoming.
When your team knows you’re invested in them as human beings, not just employees, they’ll go to the ends of the earth with you. That’s the leader I strive to be daily.
The ‘Jerry Maguire’ moment
There’s a scene in the movie “Jerry Maguire” where Tom Cruise’s character delivers that “help me help you” line. That’s leadership in a nutshell. It’s not about barking orders; it’s about partnership. It’s about saying, “I believe in you. I see your greatness. Help me help you become who you’re meant to be.”
When you build your team around that philosophy, trading ‘ME’ for ‘WE’, you create something unstoppable. Leadership isn’t easy or glamorous. It’s not about titles or awards. It’s about the late nights, the tough conversations, failures turn into lessons and the pride in your people’s success.
Winning “Progressive Leader of the Year” at ED Expo 2025 wasn’t just my achievement; it was ours. It was Jerry’s mentorship, Alex’s hard work, Tori’s resilience, Amanda’s evolution and every single person who believed in me, even when I was still figuring out how to believe in myself.
That’s leadership. And that’s what I’ll keep chasing every single day!
Mike Dickinson is the winner of the Progressive Leader of the Year award at the 2025 ED Expo. He oversees Pony Clubs nationwide, focusing on people development and high-impact events. Formerly with smaller clubs in Richmond, VA, Dickinson compares working for Jerry Westlund and the Pony Clubs to playing for the New York Yankees. Follow Mike Dickinson on X or Instagram at @iammrmiked. Email him at Mike@ponyclubs.com.
