Hey @Lou 

It’s possible to set up a two step approval rule, whereby the request first goes to the Supervisor and after their approval moves onto the People/HR Team. This scenario is highlighted in our helpcenter article on Two Step Special Approval. However, it won’t be possible to set it up for the Supervisor or the People Team/HR Team to approve this absence. The reason being is you would need to create an employee role to put not only the Supervisor in, but also the People/HR Team as members. You could technically set it up that this role then approves the absence, however it would mean setting up a new employee role for each Supervisor and the People/HR Team meaning a lot of work. So my advice here is to create a two step rule, as outlined above. 

You cannot request a certificate without setting this up within the absence settings. For example, usually for Sick Leave you can set it up that if the absence is over 2 days, a sick certificate is required. The system then recognises the period and requests this from the employee. So for your case, you would need to decide the duration for which a certificate is required and implement this in the absence settings.

For more information on this topic, here is our helpcenter guide on Set up an approval workflow with a certificate request. 

If you have any follow up questions, please let me know.

Best regards, 

Conor