My office uses Outlook and for the longest time many of us with iPhones are still waiting for a way to sync our iPhone with our Outlook Calendar/Tasks/Contacts. As of now it's comparable to pulling teeth.
Even without an exchange server, you can do quite well with an iMAP mail server, and any contact/calendaring system that uses CardDAV and CalDAV (nearly all of them do, if they don't support Exchange ActiveSync).
That way, you sync directly with the server, not Outlook client to phone (which was how it was done in the 1990s).