5 Leadership Lessons I Learned From Being a Loser

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Sometimes, losing is better than winning.
Sometimes, losing is better than winning. (Flickr)

Here are 5 leadership lessons I learned from being a loser:

1. Invest more in relationships than results. I am far from a charismatic leader. While some people walk in a room and are immediately noticed, I can be in a room for 30 minutes before someone realizes that I am not a hibiscus. I was the third head coach in three years for the team our staff inherited, a squad that had only won four games the year prior. I could tell that they were skeptical, yet also excited for change. There was so much intrigue in the new coach that we had a large turnout at our introductory meeting the winter before the 2009 season. My charisma, energy and charm was so overpowering in that meeting that our first voluntary workout featured a wide-eyed group of ... count 'em, one, two, three, four players. The program would have been better off had I had not had a meeting. I had scared just about everyone away. In hindsight, I know why.

I remember two distinct things from our initial introductory player meeting. First, I wore a suit and a tie. I wanted to set the tone for a new beginning but I may have slightly missed the mark with my disconnected habiliment. The second stark memory was a question that was posed to me by a very good player who ultimately decided not to play that season. She asked, "Why do you want to coach us?" I don't remember my answer but I clearly remember that my response was an ineffective, incoherent non-answer because I simply didn't have one. At that moment I had already lost her as a player and a few others as well. My first team meeting, which in high school is the equivalent of an introductory press conference for a college or pro coach, was a monumental flop.

The struggles continued. The night before the first practice of my coaching career the best softball player at Wheaton Academy (she also happened to be its best artist, arguably its best singer, and the-best-at-whatever-she-wanted-to-do)—not to mention our already penciled-in starting catcher—emailed to let me know that she decided that she wasn't going to play softball that season. Uh oh.

I begged, pleaded, cajoled, offered cash payments (OK, not really, Illinois High School Association) to get her to join us, but she remained steadfast in her decision. Olivia Tilly, this wonderful player and remarkable young woman, returned for her senior season the next year and went on to become an all-area player but her absence in our first season didn't help the bolster the quick turnaround I had envisioned.

Unfortunately, Olivia wasn't alone in her absence. We began our first practice with eight players in the entire program. Eight players. By the beginning of our second season we had more than 30 but we started with fewer than 10. For those of you who may not know, you usually play softball with nine. I always like to say that it was like the movie "Hoosiers," but I wasn't close to being Norman Dale. When games finally began in mid-March we did have players on our bench. Scratch that, we had a player (singular) on our bench for the first game, a stunning upset over a team to whom WA had lost the year prior, 16-1. Our lone bench player didn't show up for practice the following Monday and I never saw her again.

For the first several weeks we had players join the team, quit the team (one in remarkably dramatic fashion that included an infuriated parent making a special visit to our practice), and join the team again. Only later did I find out that even those players that I thought were on board with what we were doing wanted to quit too. That news came in the form of an impromptu after-practice meeting with WA Head of School Gene Frost, who called me in to his office after watching one of my ill-advised and mind-numbing grounder drills. He instructed me that I had to try to make practices more fun and interesting, and that I needed to show the girls how much I cared, or I was going to be a coach without a team.

I don't think our practices ever got much more fun or interesting but I knew something had to change. I was so caught up in trying to do what I thought would make us better that I wasn't building relationships. Early on in my coaching career I treated too many of our players like a means to an end; the end being a "winning" program. I cared deeply about every girl that I coached but I didn't know how to show it, especially in the short term.

To the girls' credit alone, our first team improved from four wins the year prior to our staff's arrival to 12 notches in the left column. We took our lumps but by every objective measure we were much more competitive. I built relationships with a number of girls on that first team that have been maintained to this day. Yet, other girls on that team still hate me with the intense heat of 1,000 suns. I can't say I blame them. They were a beleaguered bunch being "guided" by a clueless coach.

Here's an illustration that explains this well. Several years after I had stopped coaching I was at a game standing with one of my former players. During that game there was a play at the plate and the on-deck-hitter didn't instruct the incoming runner. I mentioned to the former player that I was surprised that the on-deck hitter didn't help tell her whether or not she should slide, and in which direction. The former player, who is now a student at Duke University, said, "Coach, you never taught us that." Ugh. While it was easy for me to notice this mundane task as a spectator, I was shocked and disappointed that I had never communicated it as a coach. The vast divide between "coaching" as a fan and actually coaching a team is Grand Canyon-wide.


Dr. Mark Rutland's

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