The Cubs and my Mom Share the Same Winning Approach We Can All Apply in Leadership

Author’s note: I received Tom Verducci’s book, The Cubs Way, as a birthday present last week.  I’m intentionally releasing this blog post, which I’ve been working on for months, before reading the book because I’m sure it covers a lot of the same bases. Though I cite the book once, I encourage you to read it if anything below hits close to home with you.


My mom and I would sit and watch Chicago Cubs baseball on TV after school in the mid-1970s, and she would take our family to one game a year at Wrigley Field each summer.  We loved watching these guys because they were the good guys of baseball.   Sure, they didn’t win much back then (outsiders called them the lovable losers), but we looked up to them because they tried hard, they smiled a lot, and they worked together.

Today’s Cubs amaze me in two ways. One, they won the World Series for the first time in 107 years (duh).  And two, they achieved this under a model of management and executive leadership that grows success from within each individual, that values each employee’s contribution, and that spreads a positive attitude like ivy across a brick wall in summer.  Here’s what we can all learn from the Cubs’, and my mom’s, approach.

Trust Your Lead-off Man     It begins at the top.  The voice of your team’s leader must make clear the values you will embrace, the character each member is to uphold, and the shared respect each should have for one another.  The term ‘lead-off man’ in baseball is the person who holds the number one spot in your batting order.  This person has proven the steady nerves, solid character, and expertise to get on base.  In our work lives, I have witnessed these traits as much in women as in men, so the term is certainly a misnomer in the translation, but that person is equally as impactful.  In my work experience, I have also found these values in management as much as in the ranks.  That’s where it starts for the Cubs as well.


Maddon Epstein ESPN
Joe Maddon and Theo Epstein (ESPN)

Five years before they won the World Series, Theo Epstein, newly appointed Cubs president, gathered the people working for all of the Cubs’ baseball operations, as recounted in The Cubs Way, by Sports Illustrated senior writer, Tom Verducci.  Epstein spoke for four days outlining the ways the organization would approach building a championship future for the Cubs.  The content of his final day had nothing to do with baseball.  It was all about character.


Enter Joe Maddon; a character, to be sure, and also a man of character.  Here are just a few examples of how Maddon set this team into a positive and sustainable direction of winning.

When You Go, We Go    Maddon set the philosophy that when a player goes up to bat, the pressure is not solely on him to create the next big moment to lead to a win that day.  Winning is a team effort in Maddon’s approach, and each batter is simply one in a series of nine who, one after another, have an opportunity to get on base or move the next guy along.  This goes back to Maddon’s days managing in Tampa where the team’s practice shirt read, 9 = 8. “Nine guys, playing hard every day, equals being one of the eight elite teams to play in baseball’s postseason,” Maddon believes.

Do What You Love & Love What You Do    One of Maddon’s long-time affirmations is, “Do not permit the pressure to exceed the pleasure.”  That explains last year’s Cubs team practice shirt which read, Try not to suck.  “Take it with a light heart. … I want them to just go out there and play like they’re in Little League,” Maddon told his players, “Like a bunch of kids having a good time. Don’t worry about making mistakes.”

Enjoy Every Day     Maddon has gone to great lengths to keep the mood light around the Cubs.  He’s brought in magicians, mimes and baby bear cubs to relax his players in preseason and allow them to bond over things other than baseball.

Maddon WGN Hippie
Joe Maddon, hippie (WGN)

One day in spring training before their championship season, Maddon drove onto the field in a 1976 Dodge van he called the Shaggin’ Wagon, wearing a tie-dye shirt and a bandana over his white hair.  As Chicago Tribune reporters observed, Maddon was “channeling his inner hippie … to show some individuality.”


Trust Your Team, Let Them Take the Spotlight    After leading Tampa to play in the World Series and the Cubs to win one, any manager could easily step up and preach their philosophy as the key to winning.  However, Maddon’s success comes from flying under the radar and allowing his players to take the lead.  He’s a champion of servant leadership.  For example, players are free to decide for themselves if they want to step into the pre-game batting cage on the road since this repetitive practice can wear a player out over 162 games.  Also, team captains are in charge of determining the dress code for players when they travel, typically a clubhouse rule set by the manager.   By empowering individual players, he creates a team of leaders.

Team Over Individual     After Jake Arrieta threw a no-hitter in 2016, the entire team celebrated after the game in teammate Dexter Fowler’s hotel suite over pizza.

Maddon NESN
Maddon empowers players to become leaders (NESN)

This party was organized by the players, for the players.  Maddon did not attend.  The idea was to allow them to connect and celebrate as a team, including the players who committed an error that night or went 0 for 4 batting, seemingly contributing ‘nothing’ to Arrietta’s accomplishment.  It was a team effort, and it was important for the players to celebrate it as a team.


Anyone Can Step up as a Leader    Fast-forward to World Series Game 7: winner take all, game tied, extra innings, rain delay.  The Cubs had just given up the lead and allowed the Cleveland Indians back in with a chance to win it all in front of their home fans.  The Cubs were bummed. The mojo was gone.

Walking into the clubhouse to wait out the rain delay, heads were hanging low.  Some players were even in tears.  That’s when Jason Heyward, the veteran outfielder, called a team meeting. “Guys, weight room. Won’t take long!”

Heyward joined the Cubs with a resume that boasted clutch hits and home runs that lifted St. Louis and Atlanta in major post-season moments.  Yet, this year, and on this night, Heyward was essentially in a slump.  He was not delivering on the field, so he was not the predictable choice to lead an inspirational speech.  Yet Heyward found it important to step up at this moment.  “I just wanted them to remember how good they were, how good we are,” Heyward recounted that night. “Know how proud of them I was and that I loved them.  That I mean it from the bottom of my heart.”

The rest is truly history.  A group of positive thinking, got-your-back, support-each-other, and just-do-your-best teammates created the ultimate winning team.  This approach to playing pro baseball has drawn players to deny more lucrative offers from other teams just so they could play on this Cubs team, under this leadership philosophy, and through this approach to enjoying every day.

This is the same good-guy philosophy and positivity that mom taught me to value as we watched the Cubbies on WGN-TV and in the near-empty 3rd-base-line seats of Wrigley Field in the ‘70s.  Win or lose, we loved these guys because they acted in a way where people are valued, respected, and loved.  It’s a beautiful way to approach life, and I celebrate it whenever I think of my mother (who is celebrating her 79th birthday on the day I’m releasing this post).  And now, I think about it whenever I remember this sweet World Series win – a lifetime in the making.


Joe Maddon AP Paul Beaty
Maddon gives Joey Belladonna, lead vocalist for the metal band Anthrax, thumbs up after Belladonna sang the national anthem Wednesday, Sept. 21, 2016, at Wrigley Field. (AP / Paul Beaty )

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