Leadership Lessons From World Series Champion David Ross

Former MLB catcher David Ross had a problem: his hands. He didn’t know what to do with them when his Chicago Cubs teammates hoisted him on their shoulders and carried him off the field like a Roman conqueror after winning the 2016 World Series in Cleveland, Ohio.

This celebratory moment might never have occurred if not for a conversation in a cramped office at Fenway Park in Boston eight years earlier. As the 2008 season winded down, the Boston Red Sox added David to their roster as filler, a safety play as they headed to the playoffs. The Red Sox would lose in the American League Championship Series, and shortly after Theo Epstein, then president of the Red Sox, would play the part of catalyst for a career-changing discussion for David.

“Let me tell you what I heard about you when we considered adding you to our team,” said Theo, as David snapped to attention. “Your reputation is that you are a me-first player. That’s not what we saw while you’ve been here with us, but that’s your reputation… and reputations die hard."

Rather than react or retract, David did something poised and honorable. He thanked Theo, and swore to himself that no one would ever think of him as a me-first player again.

He went to work, not just on his game skills but on how to become a great teammate, and put serious thought into how he could make others around him better. He came up with a list, and it’s one all leaders can learn from whether on the field or in the workplace.

Be engaged.

David began to pay close attention to all that went on around him. He focused on his interactions with his teammates and scrutinized everyone’s body language.

Think about how your teammates show up to work. Do they look tired or mopey? Are they open or tense? Do they exhibit introverted behavior patterns, like shying away from conversations? Or are they extroverted: noisy and boisterous to the point of distracting their teammates’ concentration?

By being engaged, anything you witness or any data you gather may open the door to a question or conversation that will help you and your team be better workers and finer people.

Be encouraging.

David came to embody unbridled enthusiasm. Whether he was on the field on game day or sat out for a week’s worth of games—which was often the case for most of his 15-year career—David was always on the top step of the dugout, there to high-five teammates exiting the field. He’d connect with them and comment on something he noticed them do well. While others who weren’t playing may have sulked or steamed at having to ride the pine, David became the big brother, a motivational cheerleader and a one-man support system to all the starters and subs with whom he shared a clubhouse.

As a leader, how are you encouraging your team? Are you their biggest cheerleader even when mistakes are made?

Hold others accountable.

Because David was engaged and encouraging, he was able to hold his teammates accountable. They listened to him and entertained his suggestions because he invested energy in them, focused attention on them, and forged a brotherly bond with each and every one of them.

When you care for someone, their appreciation quickly morphs into a sense of gratitude and a push toward responsibility. How do you show your team you care?

* * * 

These three approaches helped David change his reputation and he ultimately became known as an amazing teammate, earning him the opportunity to double the length of his career after that 2008 conversation with Theo. David proved to all of us that becoming a great teammate is a learned skill. And ultimately, those lessons have been instrumental in moving him in a direction that positioned him and his teams to win two World Series Championships, one with the Red Sox in 2013 and again in 2016 with the Cubs.

When that final game ended for the Cubs, David—a backup catcher—was hoisted atop his giddy cohorts and carried off the diamond as if he had broken the all-time consecutive-game hit streak or smashed a walk-off home run to win the series.

And in that moment, he just didn’t know what to do with his hands...

“Do I wave? Do I blow kisses? What do I do?”

Because for all he had done to prepare himself as a teammate, David never imagined himself on the shoulders of others. And that’s the mark of a true leader—imagining how to help others to the top and not thinking twice about where it will take you.


Don Yaeger is a nationally acclaimed speaker and best-selling author. He is a Leadercast Now speaker and has made it his mission to share David Ross’ story with the world after he and David worked together to pen Teammate: My Journey in Baseball and a World Series for the Ages. Enjoy this four-minute condensed story from Don about how David became invaluable without being most valuable.

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