From Player to Coach to Business Owner: How My Leadership Has Evolved
By Cassie Reilly-Boccia, Co-Owner of VeloU
Leadership in Different Arenas: How My Role Has Changed
When I played softball, leadership came naturally. I respected the game, my coaches, and my teammates, and I put the needs of the team ahead of my own. That mindset made stepping into a leadership role easy—I wanted to take on the hard stuff so my teammates didn’t have to.
Playing at Alabama only reinforced that instinct. The standards were clearly defined, and accountability wasn’t personal—it was the expectation. When everyone understands what’s required of them, leadership feels seamless. You lead by example, hold your teammates to the same high standard, and push toward a common goal.
When we started Athletes Warehouse, my leadership style translated effortlessly into coaching. My role was still centered around leading from the front—coaching athletes, mentoring new trainers, and setting the standard for work ethic and culture.
But as our company grew, something shifted. Leadership wasn’t just about doing anymore. It wasn’t enough to set the tone through action—I had to learn how to manage, delegate, and develop other leaders. And that transition was harder than I expected.
The Trap of “Leading by Doing” as a Business Owner
For the first half of running this business, my business partner Nick and I operated under a common belief:
"If we do it ourselves, we save money."
We packed our schedules, coaching from 6 AM to 9 PM, running admin, handling marketing, overseeing operations—all in the name of growth. But in reality, we weren’t growing.
We had bought ourselves a job.
Our company was completely dependent on us, and because we never trained anyone else to take over key responsibilities, we were trapped. The only way to keep making the same money was to keep working the same insane hours.
I found myself owning a company but stuck in a job I didn’t love anymore. And worse? I was so buried in the daily grind that I wasn’t leading my team.
And if I wasn’t leading… who was?
Redefining Leadership in Business
Transitioning from a leader on the field to a leader in business has been one of the hardest adjustments of my life. Unlike in sports, where leadership is about raising the standard for the team, leadership in business involves balancing people’s careers, finances, and futures.
Employees aren’t just looking for guidance; they’re looking for stability, growth, and a better quality of life. That weight of responsibility hits differently when someone isn’t just playing for a championship—but is working to support their family.
The Biggest Leadership Mistakes I Made (And What I Learned)
1. I Confused Leadership with Management
At first, I thought being a strong leader meant creating structure, systems, and accountability. And while management is important, it’s not the same as leadership.
✅ Management is about systems, processes, and holding people accountable to a standard.
✅ Leadership is about inspiring growth, earning trust, and helping people reach their potential.
Because I was uncomfortable in my new leadership role, I leaned too heavily on management—focusing on structure and systems rather than on truly leading my team. But leadership isn’t about just enforcing rules—it’s about making people want to follow you because they trust you.
2. I Avoided Difficult Conversations
With athletes, pushing them to grow is expected. If I told a player,
"Here’s where you are, here’s where you want to be, and here’s how I’m going to challenge you to get there,"
they’d say, “Hell yeah, let’s do it.”
But with employees, it’s different. Growth conversations come with workload concerns, compensation questions, and personal circumstances.
✅ In sports, pushing harder is a badge of honor.
✅ In business, pushing harder can feel like you’re asking for more without giving more.
I shied away from these conversations out of fear of making employees uncomfortable—but in reality, avoiding them only made things worse. Now, I focus on having open, honest conversations about career growth:
➡️ Where do you want to go?
➡️ What skills do you need to develop to get there?
➡️ Are you willing to do what it takes? If not, that’s okay—let’s find the right role for you.
By having transparent career discussions, I no longer fear these conversations—I see them as opportunities to align employee goals with company goals.
3. I Didn’t Update Roles & Responsibilities as the Company Grew
When we hired employees, we created roles and responsibilities based on what the company needed at that time. But six to eight months later, our company had evolved—and the job description no longer fit.
We weren’t adjusting quickly enough, and that created frustration. Employees were being held to expectations that weren’t aligned with reality, and we weren’t clear about how their roles needed to shift.
To fix this, we started reevaluating roles more frequently, ensuring that every employee:
✅ Knows exactly what’s expected of them
✅ Has the tools and support to do their job well
✅ Understands how their role contributes to the company’s overall success
4. I Failed to Balance Accountability with Affirmation
In sports, you expect constant feedback—both positive and negative. You get called out when you mess up, but you also get celebrated when you excel.
In business, I initially struggled to recognize and affirm my employees’ successes. Not because I didn’t appreciate their work, but because I felt uncomfortable offering praise when I hadn’t been fully honest about their shortcomings.
This created a culture where employees felt like, “Well, I was supposed to be doing that anyway.” That’s not a healthy environment. Employees should know when they’re excelling—and they should also feel safe getting constructive feedback.
Now, I make a point to:
✅ Give specific, genuine praise when employees go above and beyond
✅ Hold them accountable to high standards without avoiding hard conversations
✅ Create a culture where success is recognized and improvement is expected
The Ongoing Journey of Leadership
I’m still figuring this out.
I didn’t go to business school. I’ve learned leadership through trial and error, through failures and lessons. But I do know this:
✔️ Great leaders inspire, not just manage.
✔️ Accountability and affirmation must go hand in hand.
✔️ Honest conversations create clarity and trust.
I now focus on building a company where leadership isn’t just about doing—it’s about developing others.
If you’re a coach, entrepreneur, or leader struggling with these transitions, I’d love to hear from you. What resources have you used in order to work on yourself as a leader?
Here are my two most recent books that have impacted how I reflect on my day to day work as a leader:
The 21 Irrefutable Laws of Leadership: Follow Them and People Will Follow You (thank you for the recommendation, Alex Smith)
The Confidence Code: The Science and Art of Self-Assurance —What Women Should Know (thank you for the recommendation, Nick Serio)