COO Leadership Reality

An Unlikely Pick

Who do you think was the world’s greatest leader, according to Fortune in 2017?

This is a question I often ask in our workshops. I get all kinds of answers. Who would you say is the top leader right now?

Elon Musk. He thinks in 100-year increments and is changing the way we approach transportation and energy.

Jeff Bezos. Does anyone buy things in stores now? Amazon has changed the way we shop.

Melinda Gates. Her foundation paid out $37 billion in grants in 2015 alone.

Oprah. The most impactful talk-show host ever, right?

These are all great leaders. But not the top-rated. Do you want to know who is?

Theo Epstein. Anyone ever heard of him?

An Unlikely Approach

Theo Epstein is the President of Baseball Operations for the Chicago Cubs, and he changed the face of Cubs baseball history. More importantly, his philosophy on how to make a successful leader is remarkable. I’m by no means a baseball aficionado but I love a good leader story. Let me give you the quick synopsis.

Epstein broke a record as the youngest GM in MLB history — age 28 when he assumed the position. He led Boston to their first World Series Championship is 2004 (first in 86 years) and then again in 2007. In 2011, he was hired by the Chicago Cubs as their President of Baseball Operations, all with the hopes that he would work similar miracles in Chicago.

When a new leader comes into an organization, they quickly set a tone and tempo for how the team will move forward. Epstein did just that. He made it clear to the organization that baseball was about far more than RBIs and wins. To be a winning team, the Cubs were going to have to dig deeper into the character and tenacity of their players. Epstein sent out his marching orders to the scouts — find out everyone you can about these recruits. Scouts practically wrote books about each recruit after a thorough investigation into the character and make-up of each player.

In the book The Cubs Way: The Zen of Building the Best Team and Breaking the Curse, author Tom Verducci adds context to the scrutiny in which they recruited their players.

“Once he’d joined the Cubs, Epstein gave his scouts very specific marching orders. On every prospect he wanted the area scout to give three examples of how that player responded to adversity on the field and three examples of how that player responded to adversity off the field. … How does he treat people when no one’s looking? … What do his enemies say about him? How does he treat people he doesn’t necessarily have to treat well? What motivates him? Is he externally motivated where he wants money or followers?”

Understanding the mental, ethical and emotional make-up of the player meant just as much to Epstein as the player’s technical skills. Did he have the tenacity to face disappointment? Would he face adversity on the field as a solo player or push to be a team?

As you may recall, in 2016, the Cubs ended their 106-yr streak by becoming World Series Champions. Game 7 was a close one but the team triumphed over the Cleveland Indians. What an astounding feat Epstein accomplished!

Cubs Game 7 Newspaper Headline

Leadership That Builds Legacy

So, what makes Epstein a remarkable leader?

  1. People aren’t commodities to be traded but seeds to be planted. While many may say “people are our greatest asset,” Epstein employed a philosophy that lived that out in every facet. He was just as invested in players off the field as he was on the field. One selfish, unsportsmanlike player can ruin an entire team dynamic. Every player mattered.
  2. Challenge the norm. For years, players and teams had recruited and played according to a certain process. Epstein took a gamble that there was a better way to build a winning team. By integrating his philosophy — all of the player matters — into every facet of their organization, he built a team that accomplished their goals in new and better ways than anyone else in MLB.

    “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

  3. Sometimes the things that seem inefficient and ineffective are the best long-term choices for the culture and results you are wanting. It seems inefficient to spend time developing a deep business team, filled with strong leaders who have depth of character and are committed to the team against all odds. Can’t we just hire the smartest woman to do the job? The problem is that doing things the fast way often only gets you short-lived results.

In his 2017 Yale Class Day speech, Epstein talked about what he will tell his kids about what he learned from the epic Cubs 2016 World Championship.

“Some players and some of us go through our careers with our heads down, focused on our craft and our tasks, keeping to ourselves, worrying about our numbers or grades, pursuing the next objective goal, building our resumes, projecting our individual interest. Other players and others amongst us go through our careers with our heads up, as a real part of a team, alert and aware of others, embracing difference and employing empathy, genuinely connecting, putting collective interest ahead of our own. It is a choice. The former approach, keeping our head down, seems safer and more efficient and I guess sometimes it is. The latter, connecting, keeping our heads up, allows us to lead and every now and then be a part of something much greater than ourselves. And therefore to truly triumph. I know because I will tell them I’ve tried it both ways.”
(For the full speech, click HERE.)


You want to become an effective, impactful leader that leaves a wake of a legacy behind you. How do you start? Treat people like seeds to be planted, don’t be afraid to challenge what’s around you, and do the hard work. Keep your head up — connecting, leading, being a part of something bigger and greater. You will be glad you did in the end.

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