Im not talking about a security fix or a patch necessary to make something work properly (which would seem to include Windows XP SP2), but something that gave you new functionality so important that you just had to have it.
In my life, I remember wanting Office 98 to get long file names, or was that Office 95? Office XP tried to make interesting but little-used features easier to find, a strategy reversed by Office 2003, where a nice upgrade to Outlook became the star. None of these set the world afire.
If you are on an unfinished platform like the Tablet PC, then every update is important, but thats because you are using a work thats truly still in progress. Windows XP was a worthwhile upgrade, as was Windows 98 Second Edition, but XP really required new hardware. These days it seems OS upgrades are much more interesting than application upgrades.
There was, of course, a time in the barely remembered past when every upgrade was necessary because all of desktop computing, indeed computing itself, was still in its infancy. But as technology has matured, customers are finding that what they already own works just fine. That means software often changes only when hardware has to be replaced. That can stretch the upgrade cycle out to three, even four years.
When you ask customers why they dont buy Microsoft upgrades, the most common answer is theres no business justification for the expense. Simplified, this means Microsoft hasnt delivered enough bang for the often considerable expense, time and trouble of updating an enterprise filled with software.
The other side of this is that Microsoft misses out on revenue, finds itself supporting customers using older versions of products that it would prefer not to support, and sees slow uptake of its newest technologies.
So my nominee for Microsofts second biggest mistake is that the company created an upgrade-driven revenue stream and now finds it difficult to create compelling upgrades.
Indeed, the knock on virtually every new technology Microsoft introduces is that its too hard to implement and doesnt really do enough, especially for individual users. Im sure XML is very important, but what has it done for me lately?
I can barely imagine the shock and awe that would follow a Microsoft introduction of something important that just worked when you installed it without, like SP2, scaring the bejeesus out of people beforehand.