If you are using outlook for work, ask your IT department if they are using Microsoft Exchange for Outlook.
If they are, your best option would be to go into the mail setting on the iPad and add a new email account for Microsoft Exchange. You may need to get some info from the IT department like the Exchange Server address and domain name in order to set it up. After doing this your emails, contacts, and calendar will all show up instantly. Changing a contact or calendar event on the iPad will instantly update your desktop and vise-versa.
I work for the Public School system and set this up all the time for teachers and administrators.