The Best Manager I Ever Had

The criteria for “best manager” is quite subjective, but hopefully everyone’s had (at least) one by now.

As I mentioned in a previous article, managing people is a completely different skill set than technical job skills. Just like food, what you think is “best” can differ tremendously from someone else’s perspective.

For this post I’d like to share who my best manager was and how he treated me. It wouldn’t work for everyone, but besides being my own boss, I haven’t ever felt more free under someone’s care.

Back in 2002 on my first official day as Youth Director, my supervisor at the time gave me a job description, yet instead of saying look it over and sign it he said “edit what you like and don’t like about it.”

A bit dumbfounded I started reading over the bullet points, highlighting areas I wanted to tackle and crossed out tasks I felt were outside my wheelhouse. I remember giving it back to Keith and he was, “ok looks good, let’s get to work!”

Most people dread meetings, but because I’ve experienced some great ones, it really comes down to how the meeting is run. Keith and I differ in terms of our leaderships styles, but weekly check-in meetings usually consisted over lunch. As a guy, let me tell you, there’s no better way to talk business than over food. The meeting actually has a clear ending time (unlike most) when the check is signed.

I was given tons of autonomy which I appreciated. There was an excel sheet that I tracked all my hours in different categories. Programming was up to me as long as I explained what I was doing to the staff, parents and students. Office hours were at my discrepancy also, which was great because I believed the more I was out on the field with the youth, the more effective my work was.

Now Keith and I did have a friendship years before when he was my Youth Director and when he moved back to Arizona for many years I did visit him a couple of times and stayed with his family. That may sound soft, but I can’t emphasize how much “liking” someone outside of work makes a difference in how hard you work for that person (see my last boss).

Most managers scoff at the idea of giving away trust freely in fear they will get taken advantage of, but that’s completely tainted by your personal worldview. For example as a remote manager, you actually don’t have a choice when it comes to trust. You either give it and expect it back or withhold it and it’s never gained.

This experience of having almost complete autonomy faired extremely well for me, even influenced me to start my own business years later. Others may have preferred more hands-on leadership from their manager, but not me.

Like most things in life, you never fully appreciate things until they’re gone. Less than 2 years later Keith moved on and I was placed under his boss. Things were definitely not the same (including the relationship) to the point where I would often skip team staff lunches because of the awkwardness around the table. (Note: if I pass up free food, there’s a problem)

A manager’s job is to bring out the best in his/her team which usually takes a style adjustment for each individual to some degree. Leadership is truly an art and if you’ve ever experienced a masterpiece environment treasure it because it won’t last forever.

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