Cubs GM Theo Epstein explains the 20 Percent Rule for careers

Posted by: Chris Vannini on Saturday July 29, 2017

Photo credit: Associated Press

Originally published 1/24/17

Theo Epstein built World Series winners with the Red Sox and Cubs, but it was working his way up at smaller teams that helped him figure things out.

The current Cubs general manager joined The Axe Files podcast and talked about his career path. Show host David Axelrod recommended that young people interested in politics should work on small campaigns where they work in every area with a lot of roles. Epstein had the same advice for young people interested in sports, and it applies to any profession.

Epstein's career began by interning with the Orioles for three summers, before getting hired full-time and moving up to director of player development. He moved to the Padres and worked his way up there while also earning a J.D. degree on the side. Then he moved to the Red Sox.

“Had I worked initially at a big market team that had a bigger staff and didn’t have to be as innovative to solve problems or as aggressive with resources, it would’ve have been the same experience,” Epstein said.

In all of those moves, he was brought over by baseball executive Larry Lucchino. It’s how Epstein learned about the 20 Percent Rule: Do what your boss doesn’t want to.

I always tell kids when they’re starting out in baseball, whoever your boss is or your bosses are, they have 20 percent of their job that they just don't like,” Epstein said. “So if you can ask them or figure out what that 20 percent is and figure out a way to do it for them, you'll make them really happy, improve their quality of life and their work experience and also gain invaluable experience for yourself.

“If you do a good job with it, they’ll start to give you more. That’s what happened with me with the Padres.”

Eventually, Epstein found himself as the Red Sox general manager before he was 30 years old. The first thing he did was put a team of like-minded people around him. Like a coach building his staff, he didn’t just hire the most experienced people or bigger names. It was a group of young people like him that would have good chemistry.

“When I got the Red Sox job at 28, I had zero management experience, very little leadership experience and certainly no business school training or principles about how to manage,” he said. “Out of necessity, I ended up just pulling people who I’d worked with, were like-minded, were about the same age, who shared a passion for baseball and who I’d already worked with as peers. I respected them and trusted them and knew they were good. I pulled them close.

We had an inner circle of 6 to 8 guys, we pulled all-nighters together and went about re-shaping the Red Sox together. That next year in spring training, we lived together, rented a McMansion, ate, breathed and slept baseball and had fun. If you look around baseball now, there’s three or four of those guys have become general managers, VPs, working with teams.”

Two years later, the Red Sox won their first World Series title in 86 years. Then they won another one. In 2011, Epstein became GM of the Cubs and underwent a long process to rebuild the organization from top to bottom. It resulted in the first World Series title in more than a century this past fall.

Photo credit: USA Today Sports Images

Epstein’s description of the ingredients in a championship professional baseball are the same in any sport. It’s about the right people, not just the most talented.

“When I first started working in baseball, I felt that talent would always triumph in the end,” he said. “Talent is an exceptionally important ingredient, but with every year I’ve spent in baseball — now 25 years — I’ve gained an increased appreciation for the importance of the chemistry of the group, the importance of filling your clubhouse with as many good teammates as you possibly can, the importance of those connections, the relationships, the conversations, the buy-in to a group principle. It’s not always the most talented team, but the best group with the most talent that wins.”

That goes back to scouting, which is a lot like college recruiting. The talent you can see. The off-field evaluation of players before the draft goes back years. Epstein’s comments sounded a lot like a college football recruiter.

“Fans would be shocked if they sat in a draft room — and this is most teams — when you’re assessing a player for the draft, whether it’s a high school senior or a college junior, if you spent an hour talking about the player, 40 minutes of the conversation is about off-the-field issues, what makes them tick as a person, his background, his upbringing, what kind of teammate is he?

“… Our scouts have to get to know the player off the field really well, and they have to write a case for why we should bring this player into the organization, why he’s going to be an asset to us beyond his talent, why he fits into a group, why he can be a contributing member of a championship team.

They get to know the player over several years, chronicle the interactions with him, they list multiple examples of how the player faced adversity in his personal life and how he responded, how he faced adversity on the field and how he responded, how he treats his teammates, how he treats the clubhouse guys, what his girlfriend says about him, what his ex-girlfriends say about him, his friends and enemies, teachers, and you get a pretty good feel for the player.”

The entire conversation with Epstein and Axelrod is more than an hour long and worth a listen.

Chris Vannini is in his fifth year with and serves as its managing editor. He has previously written for the Detroit Free Press, The Oakland Press, The State News,, 247Sports and SB Nation.  A graduate of Michigan State University, Chris now lives in the Dallas-Fort Worth area.  Be sure to follow @coachingsearch and send emails to

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