Change can be incredibly difficult to sell to your users. They have their set ways of using your product, with months or years of experience guiding them towards accomplishing tasks. When you pull the rug out from under them by making your software look and behave differently, you upset their expectations, reset their muscle memory, and face an uphill battle to convince them of the greater utility of what you have created.
Take the Office 2007 Ribbon fiasco, for instance. Personally, I think that the Office 2003 user interface was terrible. It had no design philosophy. Features weren't so much deliberately added to the product as slapped in wherever room could be found. Office 2007's user interface was thoughtfully designed, with care and attention paid to the challengingly dichotomous goals of making its constituent products easy to use while surfacing the thousands of features that comprise the suite.
Of course, no good deed goes unpunished: the goals of the Office UI team really weren't the same as the goals of its users. The Office UI folks were charged with doing all of the things I mentioned above, while the users of Office only wanted to do their jobs. As cumbersome as the experience might have been, these users knew how to accomplish the tasks required of them. Forcing them to relearn almost everything about how to do their jobs is an uphill battle.
I think that Microsoft won by attrition in the end. Eventually, the enterprise customers who had been resistant to upgrading to Office 2007 had to relent, and the users adapted. I think Office made the right choice, as painful as it was.
In contrast, when you redesign a product that functions not as a painkiller, but as a vitamin (a dubious vitamin, perhaps), you will have a much harder time convincing your users to adapt. They don't have to use your product, and coupling simultaneous redesigns with reductions in features seems like a terrific way to drive away your users, regardless of how noble your intentions might be. Take the recently poorly received redesigns of Skype and Foursquare. Users raging against Skype redesigns is nothing new, but it's interesting to me to see them making the same mistakes over and over again.
I'm not sure how to guarantee the success of your product redesign, but looking at these examples demonstrates some surefire ways to fail.
Best,
Aaron
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