Seth Godin had a post today on dumb software, defined as software that's oblivious to the way he uses it. The package that set him off does not make it easy for him to delete outdated e-mail addresses, does not realize that "PM" should be the default for a 2:00 appointment ... you get the idea. He closes with:
"Desktop software (like Word) is insanely unaware of what I do, why I do it and who I do it with. Right now, the desktop folks have the momentum of the incumbent. Not for long."
I worked in IT for over 20 years, and could not understand how some products could remain market leaders. Then I read Geoffrey Moore's "Crossing the Chasm", and I understood. Once something has become a clear market leader ... like Word ... it's hell to replace. Your people are already trained in Word (or, if you don't train, they've already figured it out on their own). You've already got acres of storage in Word documents that you won't be even be able to read if you go to something else. Every one of your clients and vendors wants documents from you in Word. Well, you're not going to abandon Word for some competitor when the only thing that competitor has going for them is a superior product.
I can't think of anything, apart from software, that sells so well and is hated so much (and the hate part is justifiable). In this case, the momentum of the incumbent may well last for a very long time.