James, What is your trial license ? Do you have Office Pro Plus licensing?
Issue is the retail version of Office for Mac that you are using, it wont work.
If this is just for test run, try to create an account with a copy of Office which includes Outlook.
You need to skip the portion to authenticate it through your O365 ceredentials, if not it would look for correct licenses.
The option for O65 authentication in Office 2011 was released in 14.3 version, so you may need to try with a Mac which is not updated to that version. And you cant downgrade a version from 14.3 to 14.2 in Mac :(