Sync contacts on Outlook 2007 with Android 2.0 via usb

"there is a free software app called Google Calendar Sync
Download it and set it up to sync with your bosses Outlook profile and his Google account
You can set it so both of them sync, or desktop over writes google, or google over writes desktop

Then your phone syncs with google account and all is in synch :)

-EDIT-

Sorry I just realized you want contacts as well
In that case there is software called MailShadow which does exactly what you want
URL: http://www.cemaphore.com/mailshadow.php"