Stephanie Quilao, who writes the Back in Skinny Jeans blog, spent 9 1/2 weeks as an Enthusiast Evangelist for Microsoft. She recently left the job and her post on why she left was pretty interesting.
I created my blog business for less than $100, and it costs me about the price of a pair of nice jeans a month to run beyond my time and energy. I cannot do this with the current MS products or services. And I tried. I am making money while helping to evoke change in the beauty industries. I can use CSS and be creative in my blog design, and control what is advertised on my space. You can’t do that in [Microsoft] Live Spaces.
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As a Pro blogger, the only tool I use that is MS made is my wireless mouse, which is fabulous but, for real, there needs to something meatier than that. And again, I tried real hard to find more MS tools to integrate into my uber blogging, and could find none that were more compelling, more productive, or easier than what I already use, so why change?
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In the Valley, the trendsetters are about webware. Software is not bad, it’s just costly. What you can do on the web is just utterly interesting. People can also share much easier and faster. Companies must start looking at the web differently. Things are changing, rapidly.
Good luck Stephanie. You will be glad that you followed your heart.
p.s. Not all software is costly. Free and open source software costs nothing for the users 
Back in skinny jeans: 9-1/2 weeks: Leaving Microsoft not as sexy or tormenting
I don’t envy MS at all. Almost every criticism about something they don’t do would be equally criticised if they had of done, just by a different set of people probably.
I don’t know whether or not it would have been within Stephanie’s reach at her MS role, but is it possible that offering this sort of considered opinion internally may have steered opinion and possibly future product thinking? If not, then clearly something *is* wrong, but I’d be interested to know…