What World Series Fans and Entrepreneurs Can Learn From Cubs Coach Joe Maddon

What World Series Fans and Entrepreneurs Can Learn From Cubs Coach Joe Maddon

Joe Maddon

Image credit: Carrie Muskat | MLB.com
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Sports metaphors are pervasive in the startup world for a reason: Business is a high-stakes game. When your company is rounding first base, home plate seems far away, which is why strong, unwavering leadership is crucial.

Related: 3 Steps to Creating an Inspiring Workplace

Entrepreneurs can take a page from great coaches, such as Joe Maddon of the Chicago Cubs, whose team made it to the playoffs of the World Series. While Maddon may not have coached the National League's ultimate champs (go, Mets!), much less the final American League champs (congrats, Royals!), he has an innate ability to build trust with his players, inspiring fantastic success while keeping things light. The pennant race may be over, but Maddon’s infectious confidence and charisma, as well as the coordinated energy he inspires in his team, haven't dimmed.

The entrepreneurial coach

Excellent business leaders are usually great coaches, too. They have a knack for coaxing greatness from employees, forging a disparate group of talent into a cohesive team and creating a culture of team spirit.

Maddon’s style is one that we’ve tried to emulate at Underground Elephant. We balance the intensity of the business with fun events and surprises, to craft a relaxed environment focused on building relationships with our “players.” While Maddon, as manager of the Tampa Bay Rays, once brought penguins into his team's locker room to, in his words, “chill” out the vibe in the clubhouse, we have surprise mariachi trios serenade our office and snake charmers do their thing before a big company meeting.

Truthfully, though, it isn’t the flashy gimmicks that keep the Cubs and the Underground Elephant teams motivated -- it’s that underlying culture of leadership that rallies support in order to instill a sense of bonded community.

Calling the perfect plays

As an entrepreneur, it’s important to field not only the best players, but also the best team possible. You can have the greatest talent in the world, but if individual members don’t play well with others, you have to get rid of them. Your sales guy may bring in a mountain of business, but if he refuses to work with your marketing and fulfillment departments, he’s a net loss for your organization.

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Implement the following coaching principles into your leadership strategy, and you’ll be on your way to a strong, cohesive team:

  • Set expectations for all players. Clearly set each player’s key performance indicators. At our company, we place an emphasis on everyone playing a role in mentoring, and we expect the potential for strong leadership from every employee.
  • Coach or cut. When you have a player who isn’t performing, you need to determine whether he or she is coachable. San Francisco 49ers coach Jim Tomsula understood this when he made the call to cut linebacker Aldon Smith, who was struggling with issues off the field. Cutting someone from your team is emotionally difficult, but no startup or professional team can afford excess baggage.
  • Change the lineup. In professional sports, it isn't uncommon for coaches to shuffle players around and even try them out at different positions. You can use this same mentality at your company if one of your players isn’t performing well in a specific role. My company often puts people in different positions until we find the best fit; and we provide cross-functional training so employees have the ability to shift into new responsibilities.
  • Avoid locker room conflicts. Politics, gossip and conflict will always find their way into the office, but a good coach mitigates these negative events as quickly as possible before they become a clubhouse cancer. We use a lot of communication and transparency at my company to get out in front of conflict and gossip.
  • Inspire your team. The pinnacle of every great sports movie is the inspiring locker room speech. Startups hit a lot of skids, and at those times when you feel the most uncertain, your employees feel it, too. This is the time to step up, put on your game face and inspire your team through the tough times and pivots.

This past baseball season, we got to see great coaches like Maddon lead their teams to glory or heartbreak. Take note of what makes these coaches shine, and use those same tips as you build your own team, take the field and charge!

Related: 6 Ways to Motivate Individuals to Become a Winning Team