Wednesday, September 1st, 2010...11:41 pm

On Leadership and Management

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I’ve recently stepped into a more active management role at Sportsvite. It’s completely different than the challenges I’ve faced so far in my career and it’s starting to change my entire view of business. I know just enough to know that I’m insecure by own inexperience in management and leadership (which I’ll use interchangeable because I believe they are so closely linked) and that I’m just an amoeba of the leader I hope to be one day. But I also know that I want to learn, gain experience and grow into an exceptional leader. I think I have the seeds in me but it needs to be fertilized like Reichman’s plant sophomore year. This is a new realization for me and it’s certainly stimulating to feel my own self image mature.

How did this happen?

I’d characterize my most dominating personality traits to be independence, efficiency and free/stubborn thinking. For most of the last decade the independent side has driven much of my career direction. I’ve gravitated into entrepreneurial positions where I can better control my own destiny and have the freedom to carve my own path. Even within those positions, I’ve tried to isolate my performance from the rest of the team believing that otherwise I’d be slowed down. It didn’t help that I worked in unstructured work environments.

Now I’ve also always been driven by efficiency. In my schoolwork I was more concerned with doing the right amount of studying/work (judged by me) than with the final result or grade. Socially, I’m definitely on the lazy side of the spectrum. For better or worse this has also carried into my professional career. I don’t like to work hard unless it’s the only way to get something done. More often than not, I’ve been able to figure out shortcuts and this is much more satisfying to me. One positive is that I’m usually able to fully push my ego aside and focus on the end result or goal.

Finally, I’m a stubborn free thinker. I didn’t get accepted into my first five college choices. I was bummed out about it for awhile and one day my mom gave me that look that Brooklyn Jewish mothers have trademarked and told me that if I really wanted to get into any of those schools I could have. She was right. For whatever reason, I never bought into the path. I’d do it the same exact way all over again (Zelda, ayn rand, college hoops and fantasy sports over AP Euro studying= no brainer). I’ve had ample opportunities to follow easier career paths that could be less risky and more financially rewarding. I haven’t. I don’t want to just be successful by worldly standards. I want to be successful by my own standards (not going to get into what that means). I’ve worked in pervious organizations that have reached their goals but I was unimpressed by the way they did it. Right now, I’m kind of enamored with Tony Hsieh (Zappos) and Reed Hastings (NetFlix). They were both able to build successful companies on their own idealistic terms with their own ideal cultures.

As my career has advanced, I’ve started to realize that if I want to keep my independence it will limit my professional upside. A hired gun is just that – impactful and effective but lacking the real power of the person who hired him! Perhaps power and influence is more attractive than independence.

It seems to me that the best way to truly be powerful and influential is through management and leadership. A person who can galvanize a group of people to all work towards the same goal will always be stronger than the individual, right? I also believe that management skills are more transferable. No matter what situation, venture or project a leader can always use these skills they have developed. That seems way easier than trying to learn a new industry as well as I know digital sports media. Finally, I want to do things my way – and the only way that will happen is if I’m in a management position.

Even after writing all this mumbo jumbo I’m still trying to figure out why I’ve developed such a desire to be a leader. It’s a trait that I’ve never really exhibited before other than applying it to myself (and if I’m a leader of one than the jokes on me). I looked at the kids who were captain of my high school sports teams as ass-kissers or coach’s puppets. I never got why my buddy Hal wanted to be class president every year. Even now, very few of my friends/readers seem to have a strong prioritized desire to follow a leadership path (correct me if I’m wrong).

I’ve never had a truly great manager at any organization that I’ve ever been a part of. I don’t think this is uncommon though. A great leader is rare to find. It’s incredible difficult. It’s hard enough to manage yourself, get in your own mind, and control your own actions. Think about how hard it is to do that for a group of diverse people to all achieve a common goal.

I’m learning on the fly. I’m trusting my own instincts, trying to be extremely thoughtful, honest and soaking up as much as possible through blogs, books, conversations and advice. I’m hoping to develop a solid enough foundation so when I make mistakes I can recognize them and correct them with good decisions. I’m not a natural and for most of my life I’ve gravitated towards doings things that I’m naturally good at. It’s a weird feeling of self-awareness when I sense that I’m falling short. I try to challenge myself every day to be more considerate and less selfish. To show less frustration and more inspiration. To focus my thinking on the team and not myself. It’s my biggest professional challenge yet but hopefully I’m up to it.

It’s a bit scary for me to even put all these thoughts and ideas down on your computer screen (or in troy’s case mobile device because he doesn’t own a computer – no way you are still reading this triz!!). I’m not sure what I’m going to think when I look back and read this five or ten year from now. But I don’t think I’m getting any smarter or any sharper over the next decade (genetically, I’m destined to get fatter, snore louder and repeat myself more). But I do hope to become a better leader.