Cringley's argument rests upon the idea that Microsoft is driven too much by technology and not enough by usability. He says this is because features are owned by PM's who are technical, but I'm not going to engage that particular claim because I disagree with the first idea.
Windows' usability isn't bad. It isn't quite OSX, but if anything it is still easier for the majority of the population to stay with Windows because everyone knows it and is used to its quirks. The only "usability" problem in Vista I can think of that's big enough to be a game-changer is UAC. That's a combination of a legacy problem and an engineering problem (namely, previous versions of Windows weren't well engineered to be secure, and moving to a stricter model while maintaining backwards compatibility with apps accustomed to the looser model was bound to cause user experience headaches, unless they went a pure sandbox/VM route).
Look elsewhere in the company. Live search has fine usability but just isn't on par with Google technically. The XBox has excellent usability (and in particular was miles ahead of the competition in terms of an easy online gaming experience), but an engineering problem with the heatsink cost the company billions.
I'm not saying that technical issues are the root cause of Microsoft's problems either. There are many different problems but if I had to pick one to call the biggest, I would say a simple lack of innovation, both on the product and technical side of things. This lack of innovation is a contributing factor to two big problems:
1- Big customers are seeing fewer and fewer reasons to buy new versions of Windows and Office.
2- Microsoft is unable to execute on its traditional "fast follow" strategy where they do not create a market but are eventually able to build a product as good or better than the original innovators and then use their muscle to control the new market. Compare Microsoft vs. Netscape to Microsoft vs. Google.
tl;dr: Microsoft lets Product Managers own features, and their PMs are just engineers with different hats, so as a result MS products are badly designed.
I find this entirely unconvincing. The crux of the author's argument is that because PMs have engineering backgrounds, when development goes up against usability (whatever that means) usability loses.
Well, I doubt MS makes a practice of hiring PMs incapable of doing their jobs. I also don't see why a technical person should be considered incapable of assessing usability. In my (admittedly limited) experience, non-technical HCI people are sometimes worse at designing interfaces than programmers, whatever the oh so amusing stereotype might be. As a counterexample: While MSFT has about double the PM:Dev ratio of Google, Google PMs nearly always come from CS backgrounds too...and I don't think the author would make the same accusations about Google that he makes about MS.
I agree in principle with his overall point, however his assertion that people don't change doesn't ring true to me. Maybe I'm naive, but I think smart people DO change. Change is also called learning from our mistakes, and It's a trait I see a lot of in entrepreneurial-types. The real issue is that large companies rarely allow for the sort of 1:1 ratio of actions and consequence that are necessary for real personal change. If I'm running my own startup and I'm a jerk, I will feel the consequences of that. If I'm midlevel management at a big corp, the fact that I'm otherwise competent will protect me from the chance to see how my behavior impacts my situation poorly.
Windows' usability isn't bad. It isn't quite OSX, but if anything it is still easier for the majority of the population to stay with Windows because everyone knows it and is used to its quirks. The only "usability" problem in Vista I can think of that's big enough to be a game-changer is UAC. That's a combination of a legacy problem and an engineering problem (namely, previous versions of Windows weren't well engineered to be secure, and moving to a stricter model while maintaining backwards compatibility with apps accustomed to the looser model was bound to cause user experience headaches, unless they went a pure sandbox/VM route).
Look elsewhere in the company. Live search has fine usability but just isn't on par with Google technically. The XBox has excellent usability (and in particular was miles ahead of the competition in terms of an easy online gaming experience), but an engineering problem with the heatsink cost the company billions.
I'm not saying that technical issues are the root cause of Microsoft's problems either. There are many different problems but if I had to pick one to call the biggest, I would say a simple lack of innovation, both on the product and technical side of things. This lack of innovation is a contributing factor to two big problems: 1- Big customers are seeing fewer and fewer reasons to buy new versions of Windows and Office. 2- Microsoft is unable to execute on its traditional "fast follow" strategy where they do not create a market but are eventually able to build a product as good or better than the original innovators and then use their muscle to control the new market. Compare Microsoft vs. Netscape to Microsoft vs. Google.