Leadership Lessons from the Playing Field: Teamwork vs. Individual Excellence
By Karry Kleeman
3x SaaS Exited CRO | Board Member | Investor | Advisor | GTM Executive
Leadership Lessons from the Playing Field
Whether you’re leading a high-growth company, managing a sales team, or coaching an up-and-coming entrepreneur, leadership skills are often shaped outside the boardroom. Some of the best lessons in leadership come from the world of sports. The structure, discipline, strategy, and resilience required in athletics directly translate to the demands of business and personal success.
A long-standing debate in both athletics and leadership development is whether team sports or individual sports better cultivate leadership skills. Each offers unique lessons, and understanding the strengths of both can help shape more dynamic, adaptable leaders.
Team Sports: The Power of Collaboration and Shared Success
Team sports—like basketball, football, and soccer—offer a rich environment for developing leadership skills that emphasize collaboration, communication, and collective responsibility.
Key Leadership Takeaways from Team Sports:
- The Power of Teamwork
Success in team sports hinges on the ability to work toward a common goal. The best teams aren’t necessarily the ones with the most talent but the ones that communicate effectively and support one another. In business, leaders must foster a culture where individual strengths combine to drive success. - Adaptability and Strategy
In a team setting, adjusting to real-time changes—whether it’s an opponent’s new strategy or an unexpected business challenge—is critical. Leaders who understand how to pivot, delegate, and align their teams for success are the ones who thrive. - Accountability and Trust
Team sports teach players to hold themselves accountable while trusting their teammates to perform their roles. In leadership, trust is a non-negotiable factor. Leaders who empower their teams, while also taking responsibility for the collective outcome, create organizations that are strong and resilient. - Emotional Intelligence
Being part of a team means dealing with different personalities, strengths, and weaknesses. Great leaders understand how to manage emotions—both their own and their teammates’—to create a balanced, motivated workforce.
Individual Sports: Self-Motivation and Personal Excellence
While team sports focus on collective success, individual sports—like tennis, golf, swimming, and track & field—demand a different kind of leadership: self-leadership.
Key Leadership Takeaways from Individual Sports:
- Self-Discipline and Ownership
In individual sports, there’s no passing the ball or relying on a teammate to cover for you. The burden of success (or failure) falls entirely on the individual. This mirrors the entrepreneurial and executive leadership experience—where ownership, accountability, and personal drive define success. - Resilience and Mental Toughness
There are no teammates to lean on when facing adversity in an individual sport. Athletes must develop mental resilience to overcome setbacks. Leaders with this trait are often those who push through challenges, take calculated risks, and innovate despite uncertainty. - Continuous Self-Improvement
In sports like golf or track & field, personal growth is everything. The best athletes push themselves to improve their own performance. In business, leaders who embrace continuous learning and development not only elevate themselves but inspire those around them. - Decision-Making Under Pressure
Individual athletes are responsible for every move they make, with no one else to blame or credit. In leadership, decisiveness and confidence under pressure can mean the difference between seizing an opportunity or missing out.
Which is Better for Leadership Development?
There’s no clear-cut answer because effective leadership requires a balance of both team and individual qualities.
- For corporate executives and entrepreneurs, a mix of both skill sets is crucial.
- Sales and marketing leaders often benefit from the collaboration learned in team sports.
- Business owners, startup founders, and solo entrepreneurs thrive on the self-discipline and resilience of individual sports.
The best leaders cultivate the ability to collaborate and inspire while also demonstrating individual accountability and resilience. Those who can blend the teamwork of football with the self-discipline of golf often make the most well-rounded and effective leaders.
Final Thoughts: Leading Like an Athlete
Whether you’re on the field, in the boardroom, or leading a high-growth company, the principles of sports apply to leadership in more ways than one.
The key is to play to your strengths while learning from both team and individual approaches. The best leaders—just like the best athletes—know when to empower their team and when to take personal ownership of the outcome.
After all, leadership, much like sports, isn’t just about winning—it’s about how you play the game.
About Karry Kleeman
Karry Kleeman is a seasoned software executive, go-to-market strategist, and revenue leader. He thrives at the intersection of business growth and human connection, blending a sharp instinct for scaling companies with a deep passion for people and a commitment to infusing a human touch into the process. He is known for bringing energy and clarity to organizations—rallying teams around a common mission, driving execution, and creating momentum that fuels growth.
With a career spanning decades in enterprise software, Karry has built and led high-performing revenue organizations from early-stage startups to IPOs and strategic acquisitions. He has played a pivotal role in scaling multiple companies to successful exits, generating well over $1 billion in enterprise value. At LogicGate, he architected a go-to-market strategy that propelled the company from $1M to $50M in ARR. At SpringCM, he led the revenue function through its $270M acquisition by DocuSign. And at Mobius he helped scale the business from $3M to over $100M, culminating in a successful IPO.
Karry’s ability to inspire and energize teams is a core part of his leadership. Just as he commands attention and engagement when performing live music, he brings the same presence and intensity to leading teams—aligning them around a shared vision, setting the pace, and ensuring everyone is moving in rhythm toward ambitious goals. When he’s not driving business growth, you’ll find him performing classic rock hits anywhere he can find a live mic.
