Kathy Sierra is a technologist, a great writer, and looks good in a conference tee-shirt, no matter how baggy the schwag. She also has a great knack for analogies, like this blog post, where she asks, if your app was an employee, what kind of employee would it be?
It's clear to me from this description that Microsoft products are usually 'Anal-Retentive Guy', and getting more and more anal-retentive with each release, because Microsoft seems to think that's what we want when we ask for more security and stability in our operating system.
Like all good analogies, this is a simple exercise with really deep implications. BY all means ask yourself the 'which stereotype would it be?' question, but to get a more interesting answer, ask your employees and your customers. Each will be experiencing a different perspective of your product according to how they use it, support it, sell it and develop it.
Unfortunately all Kathy's stereotypes are negative, there's no match for products I love, like Comic Life. (Hmm... how about the guy you work with who always manages to take a menial, boring task and make it hilarious fun for you and the team?... we all know someone like that, right? ;-) OK, maybe positive stereotypes are a little hard!