Updated Oct 2009...
Desk phones (vs. cell phones)?
Desktop computers (vs. laptops)?
Which desktop/laptop OS they use?
Local shared drives (vs. cloud collaboration)?
Email! (vs. IM, Twitter, Facebook, etc)?
NB: The answers will obviously depend on the consituency. In our case, they will be different for students, faculty, and staff in different roles. For example, our students are "already there" with respect to cell phones; whereas relatively few staff are ready to give up their desk phones. Ditto email, according to many parents!