Is Theo Epstein “The World’s Greatest Leader.” The Power of Fearless Leadership to Inspire and Transform an Organization.

First things first. I am a passionate baseball fan (Mets) who grew up on my father’s knee watching baseball and inheriting his love of the game. I passed that love on to my younger son, who is working his way up the ranks of the operations side of the business.  Still, seeing Epstein’s name on the top of a list that includes, among others: Pope Francis, Jack Ma, Jeff Bezos, John McCain and H.R. McMaster really got my attention. Translation-No way! How can running a baseball team compare with running a business, religious or political organization? As a leadership coach as well as a fan of the game, I will try to make some sense of Fortune’s decision to put him at the head of a very distinguished class.

A little bit about baseball for the non-aficionados among you. When compared to football, soccer, basketball and hockey, baseball is the least team-oriented of the major sports. In fact, it is really not a team sport at all. Those other sports require repeated drills to create coordinated movements by players on the field. Except for a few plays eg. Double plays, pickoffs, pitchers covering first base or relay throws from the outfield, there is little coordination between teammates required for success on the diamond. Baseball’s essence, and truly its greatness, boils down to the one-on-one drama of pitcher vs hitter. That drama is what draws so many casual fans to watch post-season games.  But I digress. The question is, how can Theo be a great leader in a non-team oriented sport and what can we learn from him?

At the core of Fortune naming Epstein the greatest leader is his evolution from a highly successful, quant-oriented GM in the mold of Billy Beane and other “Moneyball” type executives, to one who determined that “character doesn’t just matter, it is essential.” His shift changed the way that the Cubs would evaluate players and resulted in the team’s first championship in 108 years. In the Fortune article, Epstein also spoke about players wanting to belong to something, and to feel a connection to teammates and the organization. Sounds good, but baseball history is replete with the tales of successful teams where the players literally despised each other, and in some cases actually fought in the clubhouse. Examples include the Yankees of the late 70’s; the A’s in the early 70’s, and many more. The joke about the Boston Red Sox in the 1950’s was after every game it was 25 cabs for 25 players. Of course Uber and Lyft didn’t exist then, but it doesn’t sound like those Red Sox teams would have done much ride sharing. And they didn’t do much winning either.

In considering Epstein as a great leader, his story provokes much thought about the components of leadership. It is important to keep in mind that baseball players are paid huge amounts of money. They make much more than managers and general managers, creating an environment where many players care only about themselves, not their team, teammates or organization. The baseball season is longer than ever, and players live and travel together for at least 8 months a year. In our age of the 24/7 news cycle, Twitter, Instagram etc., they are constantly examined in an unforgiving fishbowl, where schadenfreude seems to be part of the fan experience. No matter what happens on the field, today’s player interacts daily with teammates for most of the year

He used failure as an opportunity to learn and change.

The “Moneyball” philosophy has resulted in the game becoming obsessively data-driven, with baseball operations offices populated by “brilliant people with math and science degrees.” Epstein used this approach with great success in Boston where the team broke an 86-year World Series championship drought, won another Series, and appeared in the postseason six times in his nine-season tenure. But something really important happened at the end of that rollicking run that changed Epstein’s blueprint for building a winning organization and team. During his last season in Boston, the negative, me-first attitudes of a few players created a toxic atmosphere in the clubhouse, the Red Sox collapsed in September when the pressure was greatest, and Epstein took notice.

He challenged the conventional wisdom and focused on creating a culture of collaboration

When he arrived in Chicago to rebuild the perennially losing Cubs, he clearly communicated that he was going to change the way players are evaluated. Character, handling adversity on and off the field, how players treated people they came into contact with in all walks of life, and other non-athletic traits became part of the assessment process. Scouting reports became much longer and filled with non-empirical data. Long-time scouts who were unwilling or unable to adapt to the new way of doing business were let go. Said Epstein, “If we can’t find the next technological breakthrough, well, maybe we can be better than anyone else with how we treat our players and how we connect with players and the relationships we develop, and how we put them in positions to succeed. Maybe our environment will be the best in the game, maybe our vibe will be the best in the game, maybe our players will be the loosest, and maybe they’ll have the most fun, and maybe they’ll care the most. It’s impossible to quantify.” Epstein led by objectively evaluating the hits and misses of his Boston experience and shifted to a holistic approach to scouting and developing players and building a supportive, collaborative organization.

He inspired and empowered everyone in his organization to lead

The 2016 World Series was extremely close, and came down to a winner-take-all seventh game. The Cubs had lost a 3 run lead and momentum had shifted to the home team Indians when a rain delay sent both teams to their clubhouses. In the Cubs locker room, Jason Heyward stood up to speak. Heyward, who had signed a $184 million contract before the season, had a terrible year for the Cubs and was a non-factor in the World Series. Despite the fact that he was relegated to the bench on the game’s biggest stage, Heyward never complained about his reduced role or situation.  Instead, he made an impassioned speech to his teammates about his love for them and his absolute certainty about what they were going to do to win the World Series. Accounts of the game after the Cubs won were filled with testimonies from Cubs players about the impact of Heyward’s speech. Great leaders empower others to lead.

So, is Theo Epstein really the World’s Greatest Leader”? Whether you agree or not, what he has done in Chicago is a textbook demonstration of what great leaders do. After achieving historic success with the Red Sox, he fearlessly changed the winning formula that had turned around that franchise. He bucked the trend (and the “new conventional wisdom”) in a game that doesn’t change quickly or easily. He evolved, he adapted and he applied his vision of a different way of doing business.  He inspired the executives and players who work for him to stretch themselves to do things out of their comfort zone. Like all great leaders, he understood that building a successful organization always boils down to hiring, inspiring and empowering exceptional people who share a common vision and goal. Theo may not the greatest. But his greatness as a leader is inarguable. Now if we would come to New York apply his skills to the Mets, I might have to reconsider his place on the list.

What are your thoughts on great leadership?


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