I have 2 Macs (Mac mini, MacBook Pro). On my Mac mini I have no problems scheduling Skype for Business meetings from within Outlook for Mac.
However, I can't schedule any Skype for Business meetings on my MacBook Pro. I've noticed in Settings --> Security & Privacy --> Privacy tab --> Automation that Mac mini does show Microsoft Outlook selected under Skype for Business as an option.
MacBook Pro does not show Microsoft Outlook listed under Skype for Business. I've uninstalled/reinstalled Skype for Business and did the same as well for Outlook but no dice.
Assuming this is the reason why I cannot book a Skype meeting within Outlook on MacBook Pro (see screenshots).