Ben can sync Outlook to Google and then Google to iCal. That should work. Here's a technote from Apple on how to fix Exchange syncing with iCal. It's probably.

Note: Tasks are automatically selected as well. If you do not see anything in the left pane You can try to delete the preference files. After you do this, you will need to reactivate Sync Services in the Outlook Preferences pane. • Quit all applications. • On the Go menu, click Home. • Click Library folder, click Preferences folder, and then drag the following files to the Trash:com.microsoft.Outlook.SyncServicesPreferences.plist com.microsoft.Outlook.SyncServices.plist (if it exists) OfficeSync Prefs (if it exists) • Click Microsoft folder, click Office 2011 folder, and then drag OfficeSync Prefs to the Trash.

• On the Apple menu, click Restart. • Open Outlook for Mac.

• On the Outlook menu, click Preferences, and then Sync Services. • In the left pane, check the boxes next to the items that you want to sync, and then close the dialog box. • Under Select the accounts to sync, choose the account or accounts that you want to sync for the selected item type. Note: The On My Computer account includes all Outlook items that are not synchronized with a Microsoft Exchange account. • On the Outlook folder to add new items to pop-up menu, choose the location in Outlook where you want new items to be saved. 'New' items are those that are added first in a different application or device, and then synced to Outlook. • Close the Sync Services dialog box, and then on the confirmation message, click OK. Depending on the size of your calendar, the sync might take some time to complete.

You can close Outlook and the sync will still complete. For example, it will take time if you have a calendar that spans more than a year. • Open iCal and see that your Outlook Calendar information has synced. You might have to close both Outlook and iCal and then reopen to see that the calendars are synced.

Step 2: Use iTunes to synchronize your Outlook calendar with your iPhone, iPad, or iPod. Notes: • Some iPod models cannot display notes synced from Outlook. For more information, see the documentation for your specific model. • To sync your e-mail between Outlook and your device, you can add the account in both Outlook and the device. You do not need to turn on Sync Services in Outlook. • It might take a few moments for your Outlook data to appear on your iPhone, iPad, or iPod.

• When connected to your computer, your iPhone, iPad, or iPod continues to sync using the options that you selected until you change your sync options.