1.In outlook go to "File" in the top left of Outlook and click on it.
2.In the bottom left hand side you will see "options" click on that.
3.You will see this page pop up Click on the "Add-ins" in the bottom left.
4.You will now be brought to this screen.
5.Select "Content Manager Integration for Microsoft Outlook".
6.Once you have selected that in the bottom middle left you will see this.
7.Click "Go...".
8.You will then be brought to this screen.
9.Make sure to tick the box called "Content Manager Integration for Microsoft Outlook".
10.Then press "OK".
11.That should work if that doesn't restart Outlook.