The problem here is that in some work places IT is completely unresponsive to these types of requests. He needs a calendar system setup in a timely manner, not after contacting IT multiple times, speaking with different people up the ladder, and repeatedly having to babysit IT to make sure they are actually doing anything with his request. I'm not saying this is how it is at your work place (or even most), but I would guess his reluctance is due to slow IT response at his work place... I know that I've had good IT admins in the past at some work places, where requests are processed in a day or two, and slow IT admins where the simplest of requests can take weeks and repeated emails on my part for anything to be done. When one gets in the later situation eventually the "just get it done" mentality takes over and one does it themselves...