March Madness: Leadership Lessons from a Sports Enthusiast

For many professionals, it’s the end of month and the closing of Q1.  All eyes are focused on that final push to meet Q1 goals and preparing to launch the start of a strong Q2.  There is nothing more important for executive and entrepreneurial leaders right now than making certain that numbers and goals are aligned.  That is, unless you are a diehard MARCH MADNESS BASKETBALL fan and well in this case….

Photo Courtesy of Joseph Duarate/Houston Chronicle and www.timesunion.com

Photo Courtesy of Joseph Duarate/Houston Chronicle and www.timesunion.com

This would be me!  Very rarely will you have a conversation with me or attend a session with me where sports in some capacity is not compared to the lifelong leadership lessons I learned as a result of being either a competitive athlete most of my young life, a coaches wife, or basketball mom.  It’s who I am and one of the things I most enjoy.  So naturally, as I sat with my guys over the weekend and even alone at times, watching the games, I of course found some amazing leadership comparisons that I must share. These lessons are rooted in the dynamic wins of the relentless underdogs or devastating losses of the highly esteemed teams.  The lessons, the stories, the team cultures, the coaches, the players, the familial support, the commentary….everything about MARCH MADNESS offers an extraordinary opportunity for leaders to reflect.  

My Starting Five and Sixth Man Lessons:

Anticipate the WIN but never underestimate the competitive market: Every March Madness there is the rise of the underdog. Daniel takes down Goliath, and the “unknown” figures out a way to become a household name.  It happens more often than not, simply because the favorite, the team with all the measurables on paper and better record, underestimates the intensity of the competitive market (the opposing team). The job of the leader, the coach, is to make certain that whatever the market offers, the team is prepared to identify and respond to change expeditiously. As a leadership coach, I train leaders to be prepared for the curve ball.  Never let up, never slack and always anticipate an aggressive market.  Even in the uncertainty, never come to the table (to the court) so assured of the win that you aren’t prepared.  Well, at least two prominent teams over the weekend became the latest to learn this the hard way.

“Doing It All” is not the responsibility of a leader: We would be fooling ourselves if we didn’t admit that every team has a lead.  My husband, during his coaching days, typically recognized the lead guard as the extension of the coach on the floor. This is the person that drives the ship, that thinks the game through in advance of the play, the person that pushes the pace and makes certain execution takes place just as the coach desires. As the coach delegates, he/she must demonstrate an ability to duplicate themselves. This becomes increasingly more important as success ensues. After the first weekend of March Madness games, I am reminded that this person can make or break the team. This typically happens, because leadership is all too often misinterpreted as having the responsibility to…”DO IT ALL”.  This “DO IT ALL” mindset creates team isolation, it stifles offensive execution, and is the quickest way to poor performance, especially if the coach fails to redirect. Building the capacity of other leaders is not easy, but in this process you can’t forget to hold your developing leaders accountable by not only reminding them of their true roles but demanding that they execute with this understanding.  

Believe To Lead: Everything about sports and leadership in general requires a resilient and affirming mindset.  It is in the toughest moments that real leaders have an opportunity to show the depth of their tenacity.  Imagine playing on the biggest stage of your sports career and having shot a very low free throw percentage prior to the last seconds of a do or die game.  You not only have an opportunity to send the game into overtime but if you are really lucky you can actually win the game.  This is exactly what happened this weekend.  Even if history has proven unfavorable, when you shift your mindset, when you carry the confidence of those around you down to the wire...you can come up with the desired outcome.  The win!  It’s the intestinal fortitude that not only do leaders need but must be able to instill this in their people in crunch time when the weight of the entire team is on your shoulders.  The win starts with a winning mindset.  

Energized Cultures: One of the most exciting camera flashes during a game is seeing bench or role players energized on the sidelines. Moreover, it’s even more impressive when one of the impact players or floor generals recognize the energy of their teammates from the bench after an unanticipated and hard fought win.  The excitement, the zeal, the cheers, the energy; especially during these COVID times when fan attendance is extremely limited-- is the sign of a dynamic culture. How do you develop this kind of buy-in when naturally, everyone would prefer to be on the floor contributing in spectacular fashion instead of cheering from the sideline?  Well, that type of buy-in is created as a direct result of leadership having developed an energized culture.  A culture that has made valuing every individual regardless of their title, position, or responsibilities a priority.   

Win, Lose or Draw: The truth is, any team that advances to March Madness is worth celebrating.  The wins when you get there are great but it is inevitable that of the 68 teams that are eligible to play, some will lose—-because It’s all a part of the game.  This reality reminded me that teams must learn to celebrate the big wins, the little wins and leverage the lessons from the tough losses.  In either one of these scenarios, we must not lose sight that this is an opportunity to develop, for future leaders to gain exposure, for entities to come together and communicate powerful messages and for growth in a multitude of facets to occur.  This moment, this experience is an opportunity; and leaders should never walk away from opportunities of this magnitude without gaining something from the moment. This is the message that we must communicate in our spaces.  LEARN FROM THE MOMENT!!  I often say the WIN is in the work.  The work you do to get there and the work you do to sustain your passion will influence how much grow in the longterm.   Celebrate all that comes with it because every stage of the journey is a building block for the next.  WIN, LOSE or DRAW.  

Diversity Defined- In this bonus “6th man” lesson, I highlight perhaps the biggest gaffe during the 2021 March Madness games. I simply can’t imagine anything more embarrassing happening. Wait, we are talking about 2021 an extension of 2020—-so yeah, don’t hold me to that. You get the point! The ever present gender gaps that exist between women and men made headlines; yet again, as women athletes were not initially granted access to equitable training facilities and equipment. While the problem has been rectified; I find it incredibly disheartening that it took a social media firestorm for NCAA leaders to publicly admit that they dropped the ball in such grand fashion. The lingering implications of racial and gender gaps, should be forcing leaders to think more inclusively about their approaches, their decisions, their own interactions and perspectives at every turn. It should be a daily checkbox before any and every decision is made. What is comforting is knowing that a very large number of individuals are no longer afraid to call it out, enforce accountability and also contribute to closing the gap. Kudos to companies like DICKS SPORTING GOODS that stepped up almost immediately and made this incomprehensible wrong—-right. Leaders, we have work to do. Inclusivity must become ingrained in our daily happenings and until that happens my hope is that we continue to muster the courage to CALL IT OUT!


Dr. Wykesha Hayes is a growing voice in the leadership and DEI space.  Her extensive experiences in developing emerging, entrepreneurial and executive level leaders across various industries serves as the cornerstone to her approach.  As founder and…

Dr. Wykesha Hayes is a growing voice in the leadership and DEI space. Her extensive experiences in developing emerging, entrepreneurial and executive level leaders across various industries serves as the cornerstone to her approach. As founder and CEO of Keey Group, LLC, her leadership and diversity coaching and consulting programs equips leaders and organizations to perform exceptionally within the spaces they occupy.

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