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The Chicago Cubs and Winning Leadership Practices

Beyond the historic implications of this year’s World Series, the last two teams standing—the Chicago Cubs (established 1903) and the Cleveland Indians (established 1901) have a lot in common with other organizations that have been around since the dawn of the 20th century. The deeply entrenched culture of an organization that is over 100 years-old can be both a blessing and a curse for leaders. History and roots run deep and strong, but at the same time, old habits die hard and there can be plenty of agony in the process of leading necessary changes and taking risks that hold promise to result in epic wins. The Cubs have experienced plenty of both lately.

A big piece of this, of course is talent management mastery, with particular attention to assessing skill gaps, planning for future needs, identifying and investing in talent, weighing risk, and deploying that talent effectively. The owners of the Chicago Cubs made such an investment when they recruited Joe Maddon in 2014, who was fresh from leading the Tampa Bay Rays to five winning seasons, which included a stunning run of 97-wins in 2008 following 97 losses the year before. Maddon, in return has done the same with his players.

As we’ve all seen with the Cubs, while talent is essential to success, so too is solid leadership. The best talent in the world will struggle and a stellar lineup of the biggest stars will fail to coalesce without a dynamic, inspiring leader. Maddon has proven time and again his ability to bring a group of players together and motivate them to excel against the odds. Maddon’s style of connecting emotionally with his players is reminiscent of the fictional character, “Van Buren,” the manager of the beleaguered Washington Senators in the Broadway show Damn Yankees, who rallies his struggling players with these words:

“Now listen to me! This game of baseball is only one-half skill. The other half is something else. Something bigger. You gotta have heart! All you need is heart. When the odds are sayin' you'll never win, that's when the grin should start!”

Maddon understands the importance of heart; he leads with a combination of authenticity, responsiveness, and toughness. He doesn’t take himself too seriously. He’s known for reminding his players that it’s important to be inspired by history but not burdened by it. He acknowledges the extreme pressure, but also encourages everyone to be in the moment, to not forget to have fun. At one point this season Maddon sported a t-shirt with the message, "Try Not to Suck.” This week he encouraged his team members to dress up in costumes for their Halloween flight to Cleveland for Game Six.

These things are important to note because they combine to make Maddon a leader his players truly want to follow. Case in point: Ben Zobrist signed a four-year, $56 million contract to play second base, but because he believes in Maddon and his strategy, Zobrist willingly accepted assignments to various outfield positions. Consequently, the development of his teammate, Javier Baez, playing second base has accelerated exponentially—a win-win for everyone. The long-game strategy-focused conversations Maddon has with his players about these decisions leads to commitment, buy-in, and better execution. All this is not to say that Maddon doesn’t have his detractors—he does. What we in HR may hail as genius talent mobility practices have been decried by some sportswriters as reckless, “playing toy soldiers” with the players. Some of those decisions will play out (literally) on the field tonight. 

Maddon has said that his first conversation with Theo Epstein, president of operations for the Chicago Cubs, proved to be telling about what Maddon might expect in a management role. The questions Epstein posed, such as: “What’s the first thing you do when you come to the ballpark every day?” and “What do you do when a marquee player is going through a slump?” made Maddon think differently about his management style and day-to day impact and no doubt have contributed in some part to this year’s successful season. And while some of Madden’s tactics may be unorthodox, they have obviously worked. For instance, to manage burn-out earlier in the season, Maddon locked his players out of the clubhouse on the mornings of game days to prevent them from showing up too early. By making sure they had more down time, Maddon helped manage the marathon of a season. 

Consistency has been the key to the resiliency and agility of the Cubs this season. Much of this has come from Maddon’s decisive leadership style: When the Cubs were down two games to one to the Dodgers during the National League Championship Series, Maddon was asked what he said to his team to rally his team. The answer was nothing different—there were no theatrics, no dramatic displays or impassioned speeches in the locker room, just strategy and calm resolve per usual—the same predictable approach Maddon has used the entire (winning) season.