Microsoft Outlook? Easy.
Connect the iPad to the PC via USB. Click on the iPad 2's name in the PC > Select Info and you can enable sync from there. I would suggest to sync via folder and not all of Outlook.
If your Microsoft Outllok is not connected to an Exchange server then Wallace-izm have the right tip. However, I assume that you use Microsoft Outlook with Exchange which is connected to your work email. The best option is to create an Exchange Account on your iPad and any change made in either the PC or your iPad will be synced both ways. But beware that this will consume Data and you should check your data plan beforehand.
Go to Settings>Mail, Contacts, Calenders in your iPad. Now select Add Account... and select Microsoft Exchange from the list. Now you need to insert some information which you can collect from your IT guys or a Tech Savvy colleagues. Once you have set up the account, you can choose which ones you want to sync with - Mail, Contacts, Calenders etc. The first sync will take some time but subsequent Syncs will take much less time.
Now your mails will start coming into your iPad. All your MS Outlook Exchange Contacts will also shown up in your iPad contacts. You can choose how frequently your mails are fetched or you can check mails manually.