If you do not have a New Skype Meeting button along the top of your Outlook calendar, this may be because the Add-In has not been added, or there may be an Outlook/Skype version mismatch.
Checking Outlook Add-Ins
To see what Add-Ins have been enabled in Outlook, click File at the top left, then select Options. From here you will be able to select Add-Ins on the left side, look for Skype Meeting Add-In for Microsoft Office 2016 under Active Application Add-Ins.
If this appears on the list under Active Application Add-Ins, please skip to section Checking Outlook/Skype Versions
If Skype Meeting Add-In for Microsoft Office 2016 does not appear on the list you can add this by pressing the Go... button at the bottom then selecting Add… when the COM Add-ins box appears.
You will need to navigate to and select the following file:
Skype for Business 2016 - C:\Program Files (x86)\Microsoft Office\root\Office16\UCAddin.dll
Skype for Business 2015 - C:\Program Files (x86)\Microsoft Office\Office15\UCAddin.dll
Click OK to close the dialogue box and check your Outlook calendar for the New Skype Meeting button.
Unable to install Add-In
If you receive an error when installing the Add-In please reboot and try again.
If this error persists it is likely there is an Outlook/Skype version mismatch (Both Skype and Outlook need to be on either 32 or 64 bit
Checking Outlook/Skype Versions
To check Outlook version please refer to article How to check Outlook version where you will be able to see if 32 Bit or 64 Bit is installed.
To check Skype for Business version please refer to article How to check Skype for Business version where you will be able to see if 32 Bit or 64 Bit is installed.
If there is a version mismatch, please ensure re-installation is performed so Skype for Business and Outlook are both on the same version to resolve your issue (If you require 64 Bit Skype for Business 2015 please raise a ticket via the Support site).