Leadership

Chicago Cubs President Theo Epstein shares how he reinvented the team

On Nov. 2, 2016, the Chicago Cubs broke a 108-year losing streak and won the World Series. Millions of fans flocked downtown to celebrate a win that had long seemed impossible.

"You could see nothing but people, nothing but blue, nothing but exultation," Team President Theo Epstein tells David Axelrod on his podcast, "The Axe Files."

But what did it take to get there?

Epstein says that three strategies in particular helped him learn how to become a good leader and guide the Cubs to success.

1. Teaming up with others

One of the most important strategies was one Epstein learned before he even got to Chicago.

In 2002, the then-28-year-old became the youngest baseball manager ever. The newly hired assistant general manager of the Boston Red Sox quickly realized that he needed to learn from others.

"I had zero management experience, very little leadership experience, no business school training or principles at all about how to manage," he says.

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Rob Tringali/MLB Photos via Getty Images

So he formed a group made up of several young, equally determined baseball professionals. They moved in together and immersed themselves in discussing or learning more about baseball.

The deep dive into his profession helped him realize that becoming better at your job can't always be done alone. When he joined the Cubs in 2011, he carried this lesson with him.

Epstein gathered the team's managers and coaches into a hotel in Arizona and for four days debated the team's hitting, pitching and defense strategy.

More importantly, they figured out what it would mean to be a Cub.

"The hard work of turning around a franchise really began at that level," he says.


2. Building team character

Having talented individuals alone wasn't going to carry the team to success, the baseball executive says. He needed a group of people who shared the same traits. He particularly wanted to know how a player handled failure.

Scout managers were told to interview a potential player's teachers, coaches, friends, girlfriends and even ex-girlfriends. They needed to figure out how the player responded to personal and professional setbacks.

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Jonathan Daniel/Getty Images

"Failure is inherent in the game," he says. "So if you don't respond well to adversity, you're probably not going to have a long career."


3. Prioritizing long-term goals

The executive decided the team was not going to have any short term fixes. Instead of trying to hire a free agent to help the team boost its performance for a season or two, Epstein urged the team to "default to the long term."

His prioritization of the future came at the expense of the team's ranking. The team focused on player development and made big changes to their lineup over the first three years.

"It was clear we had to start anew," he says.

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Jonathan Daniel/Getty Images

He invested in the team's minor league operation, building a pipeline of talented new players. Meanwhile, the Cubs were losing game after game. But Epstein said he felt like he was "in on a secret."

That secret was that soon the team would be great.

Check out Epstein's 20 percent rule for getting ahead in your career.