One of the biggest tech news stories last week was that Steve Ballmer has announced he would retire from Microsoft within the next year. That's huge. A lot of investors have been calling for this for years.
I love Microsoft. I immediately got wrapped up in being a part of it, even though I was just one person in a company of (at the time) 90,000 full-time employees (plus contractors and vendors). There's an energy and vitality about working on the main campus that I can't quite describe. I was also endlessly frustrated by some things at Microsoft. Sometimes it was classically a big dumb company, and it's hard to change. When people ask me about the decision to leave, I say that I didn't leave because of the company, but I didn't stay because of it either.
Ballmer was routinely criticized in the press, sometimes for decision making, but more often for his personality. Yes, his "developers" chant is comedy gold. But if you ever went to a company meeting or saw him at any large gathering, there's little question that his love for the company was legit. Microsoft is important to him. You can't fault him for being a strong cheerleader.
He said a lot of things that sounded like denial of the real world to the press, but again, internally it was a different story. I saw him a number of times (actually worked in the same building for my last six months), and his candor was remarkable. He knew what the company sucked at, or where it was failing. He didn't seem to understand that the entire HR system (stack ranking and stock as compensation) was obsolete and not great for morale, but he definitely got it when it came to product failures.
It was quite obvious though that the time had come, maybe a number of years ago. He had a tough go of surrounding himself with the right people. The bigger failures were expensive. The strategic shift to a "devices and services" company came too late. More than anything though, the company is in dire need of fundamental culture change, and I just don't know how that happens unless it starts from the top.
Steve Ballmer might have been the monkey boy to a lot of people, but if I had his level of financial success with one of the most profitable companies in the world, I'd be happy to be called any name.