By "Skype for Business add-on to Outlook 2016", do you mean "Skype Meeting Add-in for Microsoft Office 2016"as the image below?
If so, refer to the following steps;
1. Close Outlook 2016 if open, then navigate to C:\Program Files (x86)\Microsoft Office\Office16 and find OUTLOOK.
2. Right-click OUTLOOK and select “Run as administrator” from the drop down menu.
3. When Outlook 2016 opens click the FILE tab in the top-left corner> Options> Add-ins> Go> check whether you have this add-on. If yes, remove and re-add it.
4. Navigate to C:\Program Files (x86)\Microsoft Office\Office16 and double-click UCAddin.dll.
2. Right-click OUTLOOK and select “Run as administrator” from the drop down menu.
3. When Outlook 2016 opens click the FILE tab in the top-left corner> Options> Add-ins> Go> check whether you have this add-on. If yes, remove and re-add it.
4. Navigate to C:\Program Files (x86)\Microsoft Office\Office16 and double-click UCAddin.dll.
Additionally, if the issue persists, follow this article to achieve your goal: https://support.microsoft.com/en-sg/help/3097122/skype-meeting-control-is-not-displayed-on-outlook-2016.
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