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Little League Lessons: What I Learned About Business Leadership from Coaching Summer Baseball

My son is seven-and-a-half years old and is the epitome of a precocious, active boy: he loves playing, watching, and consuming sports of all kinds. For the three years he’s been involved in community and school sports, I’ve always been a spectator from the sidelines. When the opportunity arose to coach one team of a four-team summer baseball league, I jumped.

I’ve been a part of the corporate world for nearly 20 years. From my earliest days in the world of spend and supplier management (and accounts payable!) to covering the burgeoning evolution of the contingent workforce and, of course, the Future of Work, there are many, many (many!) lessons I’ve learned along the way in regards to business leadership.

I’ve coached, led, and advised teams for nearly two decades. And I’m pretty sure that there are things I learned from two-and-a-half months of coaching little league baseball that escaped me all of these years. Sure, it was absolutely an exercise in patience, considering that 13 or 14 would-be second-graders aren’t always a particularly calm bunch at 5:30pm on summer nights. Rowdiness aside, the experience taught me a few things that are valuable from a business leadership perspective, including:

  • Empathy should be the foundation of all leadership styles, no matter the size or scope of a team, unit, etc. The power of empathy-led leadership is a force to be reckoned with. When leaders take the time to truly grasp the motivations, strengths, and struggles of each team member, the results are nothing short of amazing. This empathetic approach goes beyond the surface, delving into the realm of real human connection. As a result, individual potential is not only unlocked but also nurtured in an environment that values each person’s unique contributions. The impact? A team that doesn’t just function, but thrives on collaboration and innovation. In the business world, this results in workers that feel truly understood and valued…and more likely to bring their authentic self to the table. This breeds a culture of trust, where open dialogue and creative problem-solving become second nature. It’s this synergy that propels teams to new heights.
  • Leaders lead in how they act (not just how they speak). Actions, after all, are the tangible manifestations of intent. Just as my kids observed my leadership through intentional coaching, such as helping players with the follow-through of their swings and assisting them with understanding the mechanics of fielding, they also observed me “playing” the game alongside them. I pitched to them and consistently coached them on how to approach hitting. I cycled around the field, shifting to each position as the ball was in play and showing fielders how to handle groundballs, flyballs, etc. Business leaders must rethink their strategies to facilitate more hands-on teaching and support; a worker is likely to be more engaged with leadership if said leaders are joining them in operations and enterprise processes; “acting,” in this sense, enhances the overall impact of a leader’s words.
  • “Cheerleading” is a hallmark of leaders who care. Kids are more impressionable than adults, for sure. They are often tuned into the body language of parents, relatives, and other adults; thus, it is critical to maintain a positive, optimistic, and engaging attitude. When a player made an outstanding catch, I made sure to comment in the moment and when we were in the dugout. Kids who struggled at the beginning of the season were mashing singles and doubles by the season’s end, and I made sure to compliment their approach and dedication. Sure, it was great for a smile in knowing that kids (at this age, particularly) thrive on positivity from those adults that are in mentorship positions. However, I noticed something critical just a few weeks into the season: my players reacted mightily to my “cheerleading” and phrases like, “There you go, kid!” and “Nice play!” and high-fives and fist-bumps. They acted more engaged in the game and the cheerleading was somewhat contagious, as the more I cheered and complimented them, the more likely they were to do the same for each other as teammates.

From the little league field to the corporate world, the core of leadership remains constant: authenticity. Just as coaching young players requires genuine guidance, effective leadership in business thrives on real connections and real emotion. The parallels between nurturing potential, fostering inclusivity, and driving collaboration are vivid. Whether we’re talking little league or the contemporary enterprise, true leadership seamlessly weaves together emotion, action, genuine empathy, and unwavering support, creating a tapestry that fosters growth and drives success.

Tags : Consciouls LeadershipDE&IEmpathy