"As you start to work out your organizational approach to address some of these transition challenges, those will in turn generate questions and help you figure out what technologies you need to focus on," Gillen said.

As Microsoft beats the drum to attract attention to its slate of enterprise software upgrades, Cam Crosbie, vice president of IT and CIO of Equitable Life of Canada, isn't paying too much attention to it.

"It's on my radar but just at the periphery right now. It's not something I'm trying to get my head around in terms of strategy," he said.

Equitable Life of Canada is in the midst of a full desktop refresh cycle, standardizing its 550 users on Windows 7 and Office 2010, and the plan is to stay on that upgrade for the next several years.

"Ours is a 'take your time approach' to make sure there's value in a potential solution before making the jump," Crosbie said. "A lot of the marketing hype sounds quite good, but we want to make sure that whatever we're looking at has a lot of compelling business value before making the leap."