Managing technologists by day, coaching a junior-league basketball team by night

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A Father's Day reflection on leadership, teamwork and the freedom to make mistakes

Father’s Day is a time to reflect on the ways our fathers and mentors have guided and shaped us, knowingly or not. This year, my thoughts turn to my father’s decision to coach my childhood little league team. I couldn’t know it at the time, but this experience would have a lasting effect on my leadership style and the way I manage my development teams.

As a teacher, my father was hardly unfamiliar with the idea of coaching. I suspect coaching was a bit of an experiment for him, but it turns out he was a fair and knowledgeable coach, and it’s a time I look back on with fondness and appreciation. Years later, the seed of his volunteering bore fruit when my older son developed a passion for basketball and joined a local community league. Following my father’s example, I volunteered to coach.

I had hoped to have an impact on the kids, but what I didn’t expect was how much coaching would change me. On the surface, the two roles wouldn’t seem to have much overlap, but that couldn’t be further from the truth; coaching kids ended up teaching me how to become a better manager of adults.

One of the first lessons I learned was that the team only gets better when each individual gets better. In coaching, there’s a temptation to send out your strongest squad and hope they’ll get the job done. This is particularly acute in the younger leagues, where skills can vary widely and other coaches can be relied on to do the same. The strategy might work for a few games, but by the end of the season you have a very lopsided and unhappy team. The strongest players end up tired and (let’s be honest) full of themselves, and the weaker players are frustrated and unable to keep up with their peers. Come playoff time, your strategies are stale and your team is unruly.

As a manager, there are projects on tight deadlines that I know my senior developers could slash through. But that’s frequently not in the best interest of the entire team. A better idea is to have the senior developers manage the juniors through the work. Not only does it foster teamwork, it gives both the senior and junior developers an opportunity to expand their skillset. Win-win!

Another important lesson learned is to "know thy team."

Every member of a team has something different to offer. For instance, every team I’ve coached had a few players who were never going to be offensive threats, but with a little coaching and encouragement became defensive superstars. Down the stretch those defensive diamonds-in-the-rough paid dividends as I adapted my defensive strategy around their strengths to shut down our opponents’ offenses.

As a manager, I pay careful attention to my team’s uniqueness. Developers are not interchangeable. Some excel at specialized tasks like performance optimization or database design, where others may be able to whip up high-fidelity prototypes without breaking a sweat. Extending these skills requires that I’m closely attuned to where each developer shines and where they can make the most impact.

Knowing your team’s strengths also goes hand in hand with the knowledge that once your team is "out on the court," you can no longer control them.

This lesson is by far the hardest to accept. As a coach, the best I can do is give my team the raw skills I expect they’ll need and send them out to do their best. Once they’re on the court, it’s their game to play, not mine. As a coach, it’s my responsibility to provide the parameters and then let them be creative within those boundaries to get the job done. Trying to control every little action is not only a dangerous distraction, but it leaves the team without the critical ability to think for themselves. It’s not OK to second-guess their decisions, even if they are still learning.

Similarly, as a manager, I resist the urge to constantly dictate "how I would do that" unless I’m asked. For one, I frequently learn new techniques from my team by allowing them to do things their own way. More important, mistakes allow the team to grow and improve. My job is to establish the guidelines and then get the hell out of their way and let them do their job. Mistakes will happen, but so what?  Every project, every decision, is a learning experience.

Coaching has been an incredibly rewarding experience. It’s sharpened my instincts and given me an appreciation for how important leadership skills are when things don’t go according to plan. I can only hope that my sons will be inspired by my time coaching and volunteer to coach their kids someday. At least then maybe they’ll understand why their coach expected so much from them.

Vincent DiBartolo is vice president of technology with Big Spaceship.


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