Operative words - may be (both occurrences). Doing business is a risk whatever you do. Yes, there are risks in upgrading, yes there are risks in staying put. DBAs are there to help businesses determine which is the path of lesser risk and/or greater benefit.

Personally, I don't think Phil's label of "conservative" quite fits for describing larger companies. I've seen plenty of hugely adventurous decisions made, often enough to make smaller companies quail at the thought. However, companies don't become large without learning the difference between calculated risk and foolhardiness, so any system changes tend to be more fully investigated, and that takes time, hence giving the impression of conservative foot-dragging. Unfortunately, resource limitations being what they are, it can sometimes take a significant percentage of a SQL Server version's lifetime for a company to test particularly complex systems for compatibility. That's a hell of a cost just to effectively stand still.

Perhaps Microsoft would be seen in a better light if, instead of looking at its own development cycle to decide how long a SQL Server version was supported, they look at how long businesses typically use what they develop on the SQL Server platform. Are 10 year old databases commonplace? If so, support SQL Server for 10 years.

Bloodied, but unbowed....