I read his blog posts on their website and always thought he was technical and bearer of change.
Similarly, not all change is good change.
Organizational changes in the Windows org increased fan-out and forced managers to take up additional roles, and also decreased leadership opportunities in the org. The changes were in theory supposed to be better for the leaf contributor (now you're only X steps from CEO!), but in reality, having opportunities for growth is probably much more important than having two fewer people between you and the top.
What a silly antiquated notion. You want a promotion? Start a company. Poof: You're CEO. Just like that. The only growth going on in an organization which uses titles and head counts to signify career progress is a cancerous growth.
Sinofski's approach to organizational design pissed off underperforming people at the top and talented people at the bottom. As a (I'd like to think) talented employee, I quit. As an investor, I'd have backed a Sinofski run Microsoft. His model kept middle tier people making middle tier products. That's what Microsoft has become and it's going to be far easier and more successful to embrace than, than it would be to try to please everybody.
I much prefer the single BOTL (Butt on the line), with every meeting having a single decision maker.
He was also one to dictate things from up above and it was extremely difficult to understand the reasoning behind them or offer any form of disagreement. Anyone who didn't follow exactly what he wanted, was out.
So basically you'd have committees of 3's (Dev, Test, PM) filtering and relaying every decision. The people who could work the politics would get promoted and the people who understood the details would get frustrated by the top-down ambiguity and falter or leave.
Did you guys call him Signoffsky? :p
For individuals though, it makes the utterly limiting environment, where gatekeepers and not the ones with merit flourish.
On the bright side, my unscientific observation is that, in the best case, such an organization can go on like this only for one career time (~20 years). So, if you are coming in towards the end of that period, you are in for an adventurous ride.