I used to joke about leadership books as I strolled through the Red Carpet club or Borders Books. I used to joked in a snide, all-knowing twenty-something manner, with just a hint of trademark Gen-X apathy. Obviously, I didn't go to business school.
The ironic thing was that I was actually studying leadership, I just didn't know it yet. I was comparing startup culture leadership to college and professional sports. I just had no idea what I was processing, certainly I didn't appreciate leadership or processing leadership at the time.
When I was in my twenties, I worked at WebTV for Steve Perlman. I was early too. A lot of good mid-level managers one pay grade above me struggled while working for Steve. I loved working for Steve. I managed to forge a fast mutual respect with Steve that even now persists, despite the fact that I see Steve very infrequently, usually at an event or in SOMA.
Recently, Ashlee Vance from BusinessWeek reached out to me to comment on Steve as a leader. It started a retrospective that fits within my current leadership study of Roy Gilbert, Grockit's CEO. The two are very different. The two are very different from another great founder-leader I worked with, Raymie Stata, now the CTO of Yahoo!. In fact, there are very few similarities between all three.
The thing I learned most from Steve was how to learn in a founder culture. Skepticism is a good thing. But, in a functional top-down organization, the follower has to work at listening, internalizing founder thought processes and have the ability to suspend disbelief at times in order to achieve goals that seem unrealistic. Steve taught me all of that. That's why I chuckle when I see or hear someone quote Perlman disbelievingly or disparage Steve's hyper-distilled skeptical comments on "laws" of science and technical limits. Sure Steve believes in himself. But, he has earned the right to believe others will follow him too. It's not ego, it's knowing what works, for him, and everyone that is willing to listen and believe in him. That's how top-down management succeeds, IMHO.
Now, there's a lot of people that get religious about bottom-up startup culture. But, in my experience, that's a harder culture to create and sustain, very fragile, and exposed to external factors and internal employee dynamics. I believe that if you are to succeed as a key contributor, you have to be able to take direction and collaborate with top-down managers. I may be wrong, but that's my experience talking.
What I'm living now -- it's different, and fascinating all at once. Grockit is a truly interesting and an inspiring place to contribute and cooperate. And, after all of the pre-Grockit hype I heard on Roy Gilbert, I have to say that he is an impressive operator. In my late 30s, having developed the ability to recognize leadership and acts of leadership, my life and work have become so much more interesting.
Here's the really interesting thing: My leadership style hasn't changed all that much. But that doesn't mean I'm not learning. Studying leadership is engrossing. I hope everyone takes the time to observe their manager's leadership style.
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