The Struggle Leading in Sports: Balancing Fandom, Family, and Front-Office Pressure
In this latest episode of The Struggle Bubble, we sat down with Kelly Cheeseman , COO and Alternate Governor of the Los Angeles Kings and AEG Sports. Kelly has been with AEG and the LA Kings for 23 years, and I was fortunate enough to be hired by AEG/LA Kings when he was in year five. Fresh out of Ohio, I knew I wanted to break into the sports world. After a brief internship in the basement of the Staples Center with Fox Sports Net West, cutting highlights for the Angels and Dodgers, I accepted a role in the ticket office.
At 22, I didn’t have a clear concept of what good leadership looked like or how impactful it could be. I was incredibly fortunate to work under a group of leaders who would shape my perspective on leadership, motivation, and the importance of advocating for yourself. A huge shoutout of appreciation to Kelly, Matthew Rosenfeld, RICP® , Carola R. , and Chris McGowan for your mentorship early in my career.
Back then, I didn’t fully grasp the immense responsibility of leading a professional sports team, nor the pressures that come with it. But one of the most valuable lessons I learned from Kelly was about balance—staying grounded amid the highs and lows of a demanding career.
Kelly’s journey from an entry-level role to COO has spanned over 23 years, taking him through two Stanley Cup victories, challenging seasons, and the complexities of sports management. In our conversation, he shared not only his approach to leadership but also how he stays connected to his family and personal life while managing the intense emotional weight of sports fandom.
Our conversation with Kelly covers how he’s navigated the professional sports world, from the euphoria of winning championships to the emotional rollercoaster of tough rebuilding years. His insights into leadership, work-life balance, and resilience are invaluable for anyone managing the pressures of a high-stakes career.
Leading in a Non-Remote World
While many industries shifted to remote work during the pandemic, the sports world remains deeply rooted in physical presence. For Kelly, this meant facing the challenge of being physically present for games, events, and critical meetings. Managing a high-profile role that demands constant presence means being smart about prioritization. Kelly shared how he’s learned to be present for his family, even in a role that doesn’t stop.
“I had to reset my expectations and realize the game is going to happen whether I’m there or not.”
This shift allowed him to prioritize moments with his daughters, like walking them to school or attending their gymnastics meets, without feeling like he’s sacrificing his career.
Fandom is Emotional—Leadership Requires Balance
One of the most unique pressures in the sports industry is the emotional investment of fans. Kelly emphasized that leading a team like the LA Kings isn’t just about managing performance; it’s about handling the passion of a dedicated fanbase. “Fandom isn’t always rational,” Kelly explained. Fans will name their kids and pets after players or the organization, stick with you through thick and thin, but they also expect transparency and a plan when things don’t go well.
This emotional connection is what makes sports so powerful, but it also places immense pressure on leadership. Kelly’s approach is rooted in clear communication—ensuring that fans, stakeholders, and employees understand the long-term vision, even during tough seasons. The key is managing both the passion of the fans and the business needs of the organization.
Navigating the Post-COVID Sports World
Post-COVID, the world of professional sports had to adapt quickly. Kelly shared how the pandemic created new challenges, particularly in maintaining fan engagement and managing the different expectations of employees. “Some people wanted to stay remote, others thrive in the office, but in sports, you have to be there at the event.”
While the sports industry has maintained its in-person nature, Kelly and his team at AEG had to rethink their operations, balancing safety with the need to keep fans and employees connected to the experience.
Balancing Family with a High-Pressure Career
Despite his demanding role, Kelly spoke candidly about the importance of prioritizing family. As a father to two daughters, he shared how he’s made time for family a non-negotiable part of his routine: “You can’t be everywhere, and that’s okay. The game will happen whether you’re there or not, but being present for my daughters—that’s something I can’t afford to miss.”
Kelly has found that small, intentional moments with his family—whether it’s walking his daughters to school or taking them on camping trips—help him reset and stay grounded. For Kelly, the key to balance is recognizing that personal moments are just as important as professional ones, and being intentional about creating those moments.
Leadership Through Highs and Lows
Kelly’s experience with the LA Kings has been one of triumph and challenge. The team has won two Stanley Cups in 2012 and 2014, but had to navigate tough rebuilding seasons, testing his leadership in different ways. When asked how he stays motivated, Kelly said, “It’s about keeping the long-term vision. You have to stay focused on what’s ahead, even if things aren’t going well.”
For Kelly, leadership means not only celebrating the wins but also staying resilient during the tough times. His focus is always on the bigger picture, ensuring that his team, the organization, and the fans stay connected to a shared vision.
The Struggle for Balance
Kelly’s journey reminds us that balance is something we all struggle with, whether we’re leading a sports team or managing our daily lives. His approach to leadership—balancing the pressures of work, fandom, and family—offers lessons for anyone trying to navigate the complexities of modern life.
Join the Conversation
How do you balance the pressures of leadership with the demands of personal life? We’d love to hear your thoughts.
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