Yes, Windows Easy Transfer works the best if you want to transfer files, e-mails, windows settings, etc.
But as far as any program, you cannot transfer them. They will have to be reinstalled on Vista
Tell your boss that Vista isn't that bad, at least not from what I've experience. I do however prefer XP, but I don't have it now on either my desktop or laptop since I upgraded my PC's.
Windows 7 is due out soon and he might as well go ahead and get used to the technology. Although XP is comfortable, it's like the others that precede it, it will be unsupported and obsolete before long.
If you have any programs like Adobe or Microsoft Office or others that required activation when you installed them on XP, make sure to deactivate them before you install them on the new PC. Otherwise they may not activate again, unless you still have unused licenses left on the serial numbers.