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Lessons Learned from the Very Patient Chicago Cubs

CEOs often look to the best for ideas and learnings. As 2016 World Series Champions, the Chicago Cubs have a few lessons to impart.

During a baseball season dominated by public attention to politics, the Chicago Cubs achieved something remarkable: getting Americans to watch the World Series on television again, in numbers not seen for many years.

They did that first by being in the World Series, and second by winning for the first time since 1908. The joy of breaking the “curse,” and the magnitude of that achievement, was matched only by the confidence the team, its players and management had displayed in the inevitability of their seven-game victory over the Cleveland Indians.

The Cubs’ transformation started from the top when J. Joseph Ricketts, founder of Ameritrade, and his family bought most of the team from Tribune Co. in 2009 at an estimated price that approached $900 million.

“Maddon encouraged organic, “locker-room” leadership among his key players, which in many circumstances is more effective than managerial edict.

What did the new owners and their top executives, and on-the-field management, do to make World Series winners out of the Cubs after a century? And what can all business leaders learn from their storybook success?

Here are 5 lessons CEOs can pick up from the team and use in their own game plans.

1. Put the right people in place. From the team president down to the designated hitter, organizational experts marvel at how the 2016 Cubs had all the right people in all the right places. First, the Ricketts family hired as president, in 2011, Theo Epstein, who already had helped end one of the sport’s most famous droughts by buliding the world champion 2004 Boston Red Sox. Epstein brought in Jeb Hoyer as general manager and (eventually) Joe Maddon as manager – people with proven success. And they rebuilt the Cubs, a last-place club with one of the oldest rosters in baseball, by mixing free-agent acquisitions, trades and strong draft choices.

2. Write a road map. Among his first steps, Epstein put together a large organizational playbook for how the “new” Chicago Cubs were going to go about winning again, a sort of blueprint for the team’s new direction. It covered everything from team culture to what type of players the Cubs would seek out to how their minor-league affiliates were to operate.

3. Embrace your destiny. After the Cubs’ turnaround was manifest in 2015 and the team made the playoffs but not the World Series, the entire organization – front office down through the bench – embraced the idea that 2016 was going to be the year the Cubs won it all. And, fueled by a breathtakingly successful start to the season, they never backed down from the goal despite the notion that hubris could set in. Embracing their destiny worked.

4. Ride your superstars. Though the Cubs assembled a team where every individual player provided an important ingredient, one of Maddon’s coaching principles also was to count on his superstars to carry more than their share of the burden of winning. He did that with closer Aroldis Chapman by riding the relief pitcher for the longest stint of his career to help the Cubs win Game Six and stave off elimination; then Maddon, arguably, left Chapman in Game Seven too long, and he lost the Cubs’ lead, only to be picked up by his teammates as they won in extra innings. Maddon tried a similar approach with slugger Kyle Schwarber by pressing him into very successful designated-hitter duty DH despite the fact that he had suffered an early-season injury which was supposed to keep him out for the entire year.

5. Count on organic leadership. Maddon’s low-key approach was made iconic as World Series TV cameras could scarcely get a change in expression out of him. But one reason the skipper could succeed without histrionics is that he encouraged organic, “locker-room” leadership among his key players, which in many circumstances is more effective than managerial edict. Many observers of the national pasttime believe that’s exactly the inherent strength that kicked in during the17-minute rain delay before Game Seven went into extra innings. Cubs’ clubhouse leaders exhorted their teammates to keep believing in the dream even though they’d just given up the lead.

In just five years, the new Cubs built a world-leading organization from a laughingstock. Business leaders can do the same in any industry.


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