Leadership Lessons from the DugOut

from the ball field to the board room

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about

I have over experience as a baseball coach, working across rec leagues, travel baseball, travel softball and high school programs. I’ve coached players ranging in age from 4 to 20, including those in our college-age travel teams. My own baseball journey began at age 7 and eventually ended on a Division 1 College Baseball team. In addition to my sports coaching background, I have over than 20 years of experience in the corporate world of leadership development. Over time, I’ve come to recognize that many of the lessons learned on the baseball or softball field translate directly to the broader world of leadership development and people management. I’ve been fortunate to learn from many outstanding baseball coaches and corporate leaders along the way.

  • Where Data Ends and Instinct Begins

    In both baseball and the professional world, the amount of data available to us has grown tremendously. Metrics, analytics, dashboards, and reports offer insights into everything from performance trends to individual behaviors. For coaches, players, people managers, and business leaders, this data can be incredibly useful, but also overwhelming—and it’s not always definitive. The real challenge lies in knowing when to lean on the data, and when to trust your instincts.

    Take baseball, for example. A coach might have a spreadsheet or an iPad full of stats showing unfavorable pitcher-hitter matchups. The data may say it’s time to pull the pitcher. But maybe the coach sees something else—the pitcher’s body language, his rhythm, the confidence he’s showing on the mound. Maybe he’s locked in. Letting him stay in, even against the statistical odds, might not just win you the inning—it might earn the player’s long-term trust and elevate the culture of your team. Sometimes it won’t work out. But part of leadership is owning those calls and recognizing that people aren’t robots, and performance isn’t always predictable.

    The same is true in the corporate world. Imagine a sales representative whose numbers are off the charts. The data says they’re performing at an elite level. But as a leader, your instincts tell you something’s off. Maybe their success is due to temporary market conditions, or perhaps the bulk of their revenue is coming from one large client that isn’t sustainable. Even though the dashboard is lighting up green, your gut is telling you to dig deeper, or maybe even consider rebalancing their territory to protect the long-term integrity of your sales strategy.

    In both scenarios, the data gives you information—but it doesn’t make the decision for you. That’s your job as a leader. Data should inform your judgment, not replace it. The best leaders know how to balance the objective with the intuitive. They understand that numbers are powerful, but so is experience, human behavior, and context. They ask themselves: What is the data telling me? And just as importantly: What is it not telling me?

    There’s no formula for getting this right every time. But with experience, reflection, and feedback, you sharpen your ability to discern when to follow the numbers and when to follow your gut. And over time, your “gut” becomes more than a feeling—it becomes informed intuition, shaped by everything you’ve learned along the way.

    Ultimately, leadership is about making the tough calls. Sometimes the safe bet is to follow the metrics. Other times, the right move is the one the data can’t quite see. Learning to walk that line—confidently and responsibly—is what separates good decision-makers from great ones.

  • Adapt Your Style to the Individual

    Effective leadership—in both sports and business, —requires more than understanding the overall dynamics of a group. It demands the ability to recognize and adapt to the unique needs, personalities, and motivations of each individual. Just as every team has its own collective identity, every person on that team brings their own background, communication style, and emotional makeup to the table. Successful leaders take this into account and tailor their approach accordingly.

    In baseball , for example, you quickly learn that what works for one player may not work for another. Some players respond well to direct, even blunt, feedback—they appreciate the clarity and rise to the challenge. Others may shut down or lose confidence if approached the same way. The art of coaching, then, lies in knowing who needs a push and who needs support, who benefits from space to fail and learn, and who needs guidance before mistakes are made. The same principle applies to leading teams in the workplace. I always recognize this during “mound visits”—when the pitcher might be struggling or needs to rest the coach goes for a visit. I always tried to learn exactly how to help that pitcher respond. Sometimes it was direct and to the point sometimes it was with a joke. Knowing which pitcher needed what is the key.

    In the corporate world, understanding how to treat individuals isn’t about favoritism or lowering standards—it’s about helping each person perform at their best. Some employees thrive with autonomy; others excel with structure. Some value public recognition; others prefer quiet validation. Leaders who take time to learn these preferences build stronger trust, increase engagement, and drive better performance across the board.

    Of course, this kind of individualization takes effort. It requires observation, listening, and a willingness to ask questions. But the payoff is significant. When people feel seen and understood, they’re more likely to commit, collaborate, and contribute meaningfully to shared goals.

    Adapting your style isn’t about being inconsistent—it’s about being intentional. It’s about showing respect for the differences that make each person valuable. Great leaders don’t treat everyone the same; they treat everyone with the same level of care, curiosity, and commitment. That’s what unlocks potential—one individual at a time.

    5. Knowing When to Trust the Data—and When to Trust Your Gut

    In both baseball and the professional world, the amount of data available to us has grown exponentially. Metrics, analytics, dashboards, and reports offer insights into everything from performance trends to individual behaviors. For coaches, players, people managers, and business leaders, this data can be incredibly useful, but also overwhelming—and t it’s not always definitive. The real challenge lies in knowing when to lean on the data, and when to trust your instincts.

    Take baseball, for example. A manager might have a spreadsheet or an iPad full of stats showing unfavorable pitcher-hitter matchups. The data may say it’s time to pull the pitcher. But maybe the manager sees something else—the pitcher’s body language, his rhythm, the confidence he’s showing on the mound. Maybe he’s locked in. Letting him stay in, even against the statistical odds, might not just win you the inning—it might earn the player’s long-term trust and elevate the culture of your team. Sometimes it won’t work out. But part of leadership is owning those calls and recognizing that people aren’t robots, and performance isn’t always predictable.

    The same is true in the corporate world. Imagine a sales representative whose numbers are off the charts. The data says they’re performing at an elite level. But as a leader, your instincts tell you something’s off. Maybe their success is due to temporary market conditions, or perhaps the bulk of their revenue is coming from one large client that isn’t sustainable. Even though the dashboard is lighting up green, your gut is telling you to dig deeper, or maybe even consider rebalancing their territory to protect the long-term integrity of your sales strategy.

    In both scenarios, the data gives you information—but it doesn’t make the decision for you. That’s your job as a leader. Data should inform your judgment, not replace it. The best leaders know how to balance the objective with the intuitive. They understand that numbers are powerful, but so is experience, human behavior, and context. They ask themselves: What is the data telling me? And just as importantly: What is it not telling me?

    There’s no formula for getting this right every time. But with experience, reflection, and feedback, you sharpen your ability to discern when to follow the numbers and when to follow your gut. And over time, your “gut” becomes more than a feeling—it becomes informed intuition, shaped by everything you’ve learned along the way.

    Ultimately, leadership is about making calls. Sometimes the safe bet is to follow the metrics. Other times, the right move is the one the data can’t quite see. Learning to walk that line—confidently and responsibly—is what separates good decision-makers from great ones.

  • Know Your Team’s Personality

     It may seem obvious that coaching a group of 5-year-olds requires a different approach than coaching 18-year-olds. But over time, I’ve come to understand that tailoring your approach to the team goes far beyond age or experience level. Whether in youth baseball or the corporate world, every team has its own unique personality—and great leaders recognize and adapt to that.

    Some teams are highly self-reliant. Once you set a clear direction, they execute with minimal oversight. They thrive on autonomy and appreciate being trusted to manage their own work. Others may need more structure, encouragement, or ongoing feedback to stay on track. Some teams are composed of seasoned experts who bring deep experience and confidence, while others are newer to their roles and still building their skills and team cohesion. The composition and maturity of the group should directly inform your leadership style.

    In baseball, I’ve coached teams that responded well to intensity—where being direct, loud, and demanding brought out their best. I’ve also coached teams where that same approach would have backfired, shutting players down or creating unnecessary tension. Learning how to read the group, understanding their mindset and emotional makeup, helped me adjust how I communicated and led.

    The same principles apply to organizational leadership. A one-size-fits-all approach rarely works. Leaders must take time to observe, listen, and evaluate the collective energy, confidence, and capability of the team. Then, they must adapt their communication, motivation, and support strategies to fit that team’s needs.

    Ultimately, knowing your team’s personality—and leading accordingly—is what builds trust, fosters performance, and brings out the best in people. Whether on the field or in the office, success often depends not on having the perfect plan, but on having the right approach for the team in front of you.

  • Building a Well-Rounded Team–Balancing Specialists and Athletes

    In today’s competitive environments—whether in youth sports or professional workplaces—leaders must thoughtfully construct their teams with a balance of versatility and deep expertise. In baseball, this often means having a mix of players who can do a bit of everything and those who focus their energy on excelling in one specific role. The same holds true in organizational leadership. High-performing teams typically include both “athletes”—individuals who are agile, adaptable, and capable across a range of tasks—and “specialists,” who offer deep knowledge and mastery in a particular area.

    This concept is especially visible in youth baseball. While there’s growing concern about early sports specialization, that’s not the kind of specialization I’m referring to. Instead, I’m talking about team roles. Some players can effectively move between positions, contributing on the field, at the plate, and sometimes even on the mound. Others, however, focus entirely on one skill set—like pitching. In baseball, we call these players “POs,” or Pitcher Only. They don’t bat or play other positions. Pitching requires so much physical preparation, recovery, and mental focus that it makes sense for some players to devote their full attention to it.

    This approach carries directly into the workplace. Early in my professional career, I found myself drawn to what I called “athletes”—team members who could do multiple things well. These individuals were resourceful, curious, and flexible, and could be deployed in a variety of roles. Especially in fast-paced or evolving organizations, these team members were incredibly valuable. They could step in where needed, quickly learn new skills, and bring a wide-angle lens to the team’s goals.

    But as my leadership experience grew, I came to better appreciate the value of specialists. These are the team members who focus deeply in one area—such as instructional design, data analysis, or workshop facilitation—and elevate the overall performance of the team through their technical depth and precision. Their expertise ensures quality, drives innovation, and often becomes a critical backbone of the organization’s success. In many cases, trying to spread these individuals too thin or pull them into unrelated tasks would reduce their impact.

    The key insight is that successful leaders recognize the need for both. Versatile contributors add flexibility and resilience to a team, while specialists bring focus and excellence. One is not inherently better than the other; the value comes from how each complements the other. Just like in baseball, where a utility player and a starting pitcher may have very different responsibilities but equal importance, the workplace thrives when we build teams with the right mix. As leaders, it’s our job to identify and develop both types of talent—those who can wear many hats and those who are deeply invested in one. When we strike the right balance, we create teams that are not only well-rounded, but also built for sustained success

  • Find Your Trusted Voice

    Find Your Trusted Voice

    Great leaders—whether on the baseball field or in the business world—needs a trusted voice. This is someone on your team who feels confident enough to tell you the truth, even when it’s not what you want to hear.. In sports, that trusted voice can be the difference between making the right call and missing something important. In business, it can be the key to unlocking better team performance and avoiding costly missteps.

    In baseball, that voice helps you uncover what’s happening off the field.. Is a player struggling off the field? Is someone being mistreated or bullied? Are the drills you’re running actually producing results? The answers to these questions don’t always come from formal evaluations or surface-level conversations—they often come from the people who know the team intimately and are paying close attention. I experienced this firsthand during a 16u travel game. One of our players had taken a ball to the head before the game, but I didn’t catch the signs of a concussion right away. In the dugout, a player I trusted came to me and said, “You have to get him out of the game—something’s not right.” Because of the trust we had built, he felt empowered to speak up. That moment potentially prevented a much more serious situation. Without that voice, the outcome could have been harmful for both the player and the team. The workplace is no different. Leaders often operate at a high level, making it easy to miss the day-to-day details that impact performance. If you’ve earned the trust of a team member, they may step in and share a critical insight—perhaps about a struggling employee, a broken process, or a looming conflict. These moments only happen when someone feels safe enough to speak honestly and knows they will value their input. Creating this kind of trust doesn’t happen overnight. It requires leaders to listen with openness, respond without judgment, and demonstrate that feedback—is taken seriously without consequence.. It also means setting a tone where truth is the most important thing. Whether you’re leading a team on the field or in the office, find that trusted voice. Nurture it. Listen to it. Because in the moments that matter most, it’s often that one voice that can help you make the right decision for the people you’re responsible for.