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The Cubs’ Joe Maddon Is Keeping It Weird (And Thank Goodness for That)

Why mimes and pajamas are part of a winning managerial style

Manager Joe Maddon celebrates with the team after a one-game Wildcard playoff win in 2015.   Phot: Nuccio DiNuzzo/Chicago Tribune

Before we launch headfirst into the sixth-month-long baseball season tonight, let us a toast an eventful Spring Training. Hardly a week went by without some fresh stunt from manager Joe Maddon: mimes and guitarists and (real, live) bears, oh my.

For Maddon, this is nothing new: Last season, after a five-game losing streak, he invited a magician into the locker room to pass a little magic on to the Cubs. They won their next three games. On a long flight home from LA, he encouraged players to wear footie pajamas for maximum comfort. 

While Maddon’s approach is undoubtedly odd, it is far from unpopular: He was named the best manager in the National League for his unorthodox efforts.

So why does Maddon’s leadership style work? Brayden King, a Kellogg School of Management professor who teaches a class on business leadership through the lens of professional sports, says Maddon’s leadership is similar to what you see at a lot of modern tech companies. “What Maddon wants to do is create a culture that rewards players for good work but doesn’t limit their inventiveness and individuality,” he says.

Many of Maddon’s techniques work for managers on the cutting edge of business, and they can work for you, too. Here are six notes from Maddon’s playbook: 

1. Always be surprising

There’s a slogan popular among the higher-ups at Google: “You want people to be surprised continually.” The logic goes that consistency leads to complacency. That’s why it’s important to incorporate surprise into the everyday. Nothing puts the kibosh on routine play like an impromptu karaoke session or two.  

2. Present a united front

“If you think you look hot, wear it. That’s our dress code,” Maddon told reporters last month. That said, the most memorable outfit any player wore last season might be 6-foot-5 Kris Bryant’s XXL Teenage Mutant Ninja Turtles onesie. Leigh Thompson, who teaches negotiation and collaboration (also at Kellogg), says that pajamas might serve a greater function. 

“When people all wear the same thing at once, like a team T-shirt, they form a stronger identity as a group,” Thompson says. “Something as absurd as pajamas might amplify that effect.”

3. Trust your team

Relative to most baseball (and business) managers, Maddon runs a relaxed operation. King stresses that it’s not a matter of having fewer rules than your average manager—Maddon almost certainly doesn’t. Rather, Maddon relaxes dress codes for the same reason that Google allows employees to drink on the job: He has total confidence in his team to be, if not the best in baseball, playing each game to best of their ability.

4. Be selective 

That degree of trust doesn’t come naturally. King says, “You have to be very selective, not just for skill competence but also for personality. The front office isn’t just looking for talent, but for the kind of players who work well in a Maddon clubhouse.”

5. Balance is key

“A lot of companies now recognize that employees work more efficiently when they don’t spend as much time on the job,” says King. “One of the biggest threats to efficiency is that people think they need to be in ‘work mode’ all the time.” 

That’s why Maddon forced players to skip hitting practice for seven games in the dog days of August last year. He called it American Legion Week, a tribute to playing baseball “the old-fashioned way.” It was also a chance for players to rest up before the onslaught of postseason play.

6. Get silly

According to Thompson, nothing cements a group like shared, silly experiences. “Getting silly helps you learn to stop judging each other, and you want that because judgment shuts down creativity.”

Thompson says that a group therapy session might smack a little hippie-dippie for the ball club (or, for that matter, the workplace). “The next best thing, if I had to write a prescription, is baby bears and pajamas,” she says.


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