Which Outlook are you using? Also, for me it didn't work the first time. I uninstalled and then reinstalled it on the Computer. Then I restarted the phone, shut off and turning on. I connected the USB and when on the phone the selection pop up, Charge, mount, HTC Sync and one other, I hit HTC Sync and the drivers started to load on the computer. I opened up Sync on the computer and manually did the sync. Now it works perfectly fine. You might want to go on the HTC forums for help.
Here is the link. It seems some people are getting working and some are not.
HTC Community
I am using Outlook 2007. I will check out the HTC forums. Thanks for the link!