For one, Skype and Outlook works only for Skype for Business users. However, there are a few things you need to keep in mind before you proceed. You will see the reminder pop-up when the meeting draws near just like with most Skype meetings. The good thing about Skype meetings is that Outlook users will view the option to join the Skype meeting at the top of the invite, whereas non-outlook users, such as Gmail users, will see the option to open the Skype web app in their invite. Then you can add the remaining details like Agenda and that's about it. After that, Outlook will generate the corresponding Skype meeting link. Hence, you must pick the start time and end time beforehand. Now, whenever you click on it, a link for the meeting will be auto-generated and pasted on the meeting body. Step 2: Select New Meeting and you will see the Skype Meeting icon on the ribbon. Once done, head over to the main window of Outlook and click on Home > New Items. You should notice the said Add-in in the list under Active.
To do so, click on File > Options, and select Add-ins from the menu. Step 1: Before you add a Skype meeting to Outlook, you must check if your Outlook already has the said add-in. How to Add Skype Meeting to Outlook Meeting