How Theo Epstein Wins (And How You Can Too)


Theo Epstein became the youngest GM in the history of Major League Baseball when the Boston Red Sox hired him at the age of 28. In 2004, the Red Sox won their first World Series championship in 86 years and won another championship in the 2007 season.

In 2011 he resigned from his job in Boston to become President of Baseball Operations for the Chicago Cubs.

The Cubs finished the 2016 season with best record in Major League Baseball, winning over 100 games for the first time since 1935. They will be facing the Cleveland Indians, in the World Series, tomorrow night.

So how he did win a World Series with the Red Sox and is on track to do it again with the Cubs, who haven’t won the World Series since 1908.

What can we apply to our own careers?

Know Your Business: It takes passion, almost an obsession, to become an expert in your business. Do you sell microprocessors but have never taken apart a computer? Do you design ovens, but never cook? You’re probably not going to be the most successful in your field. It sounds simple but you need to understand your business fully in order to be successful. When starting his career in San Diego, his General Manager told him the best way to learn the sport was to sit behind the plate and run the radar gun. Every night he sat there, learning what a fastball looks like, analyzing very players batting stances, etc. Become a sponge and learn everything that you can about your business.

Use Data To Make Decisions: Moneyball is a book by Michael Lewis about the Oakland A’s baseball team and its general manager, Billy Beane. It focuses on the team’s analytical, evidence-based approach to putting together a baseball team. Epstein has believed in this since he was a kid reading Bill James’ By The Numbers, a statistical analysis of major league players. While with the Red Sox, he sent interns to the NCAA headquarters to search through 30 years of stats to see if there were any trends to becoming a successful major leaguer. Don’t always rely on your gut to make decisions, see what the numbers say first.

Have A Vision: All successful leaders have a vision. When Epstein took over the Cubs, he had a meeting in a Mesa, AZ hotel and invited 150 scouts, coaches and front office personnel. There he created a vision for the Cubs: He clearly defined what the personality of the players would be, what the pitching would look like, what their offense would consist of, etc. That vision spilled out onto the field. Whenever they would see an a player make exceptional play, they would yell, “That’s a Cub.” This was meant as a compliment, despite the fact that the team was losing 100+ games.

It’s All In The Details: Theo Epstein is obsessed about details, whether it’s drafting a player or interior decorating. According to Sports Illustrated, “He obsesses over details, from the draft board to the recruiting videos…to the time he spent trolling taxidermy websites to find the perfect stuffed bear for the cafeteria. Last year, while the Cubs were building a new clubhouse, he hyper focused on the number of inches between the couch and the ottoman.” Remember, how you do anything is how you do everything.  You can’t ignore the details and expect a great outcome.

Have Fun: How else does Epstein get interns to work 100+ hours? He hits golf balls in the office while kicking around ideas. He rented a house in Cape Coral, where he lived with and eight front office personnel. They would carpool to the office, blast music, play poker, work out, and eat meals together. He realized that changing a culture takes buy in from everyone. It needs to be embraced by the majority of the team.

There’s More To Life Than Work: While Epstein was with the Red Sox, he attended the funeral of a longtime club employee. The coffin had a Red Sox logo on it. He was quoted as saying, “I don’t want to be buried in a Red Sox casket.” He grew up after getting married and having kids: He started a foundation to help inner city youth and spent more time with his family. People close to him think that he will eventually pursue a career outside of baseball.

A famous Chicagoan, Ferris Bueller said, “Life moves pretty fast. If you don’t stop and look around once in a while, you could miss it.”

Go Cubs!

This article originally appeared in Forbes on October 24, 2016.  For more Forbes articles, please click here.

InspirationTom Ward