Any reason why you're looking to sync over something as antiquated as a cable?
In all honesty, there is some legitimacy to the question. I haven't synced to my PC since my old Palm days. If you're using a personal phonebook it's much cleaner and easier to sync Outlook to your Google account, if it's corporate you'll probably want to check with IT about how to do it wirelessly.
No special reason other than not wanting to put all contacts out there for security reasons. Most are business contacts. I use a stand alone version of outlook. Not an exchange server.
Hmmm, you may want to check the contacts in the Google account associated with the phone. By default the phone will sync with "the cloud" which, in this case, is Google.
I understand what you say about not wanting to sync all your contacts to "a cloud" for security reasons. Although this is a staple feature of Android and Google, some people are not comfortable with it.
A simple search over at AppBrain for "Outlook Contacts" yields results.
I tried DejaOffice but it wouldnt work for me and tech support was spotty. Next one up to try is Gsyncit. I think those are about your only options for syncing Pop3 outlook contacts with your Android contacts.
This is an awesome App. I originally made the csv file back in december to transfer to google which worked but it did not sync all my repeated Birthdays and events.
But this just did!! Even reinstated every date before I got my X.