In both my outlook on my MacBook Air and my boss' outlook on his MacBook Air, neither one has the 'permissions' button able to be clicked. It is gray. When I right click on a calendar listed on the left no option for 'share calendar' or 'add delegate' or any other sharing choice appears. 

My boss leaves the country tomorrow and I need to have access to his calendar before he leaves. Can anyone help? We are both using Microsoft Office 2011.

Hi,

Which account type are you and your boss using?

Share calendar is only available for Exchange account. If the Exchange server is correctly configured then it should work.

Please contact your IT admin and make sure the EWS settings are setup correctly.

Since this is the forum to discuss questions and feedback for Microsoft Outlook on Windows OS, better to post your question to the forum for Mac

http://answers.microsoft.com/en-us/mac/forum/macoffice2011-macoutlook/

The reason why we recommend posting appropriately is you will get the most qualified pool of respondents, and other partners who read the forums regularly can either share their knowledge or learn from your interaction with us. Thank you for your understanding.

Steve Fan
TechNet Community Support