Time Off / HR Request Board

I have created a form + board, accessible only to managers, for employees to submit Time Off requests.

Current workflow:
-Employee completes a form that creates an item in a Manager-Only baord
-Manager then has to review the request and approve/deny
-Once approved, automation to create a new item in a separate board, accessible to the entire company, to track employee time off on a shared calendar

I am looking for a way to flag an incoming request (alerting Manager - “People” column) - in the initial Manager-Only Board, if there is another employee that has already been approved for those days. Essentially, need to flag for the manager to review the impact of the incoming requested PTO in terms of how many other team members will also be out on those same days.

I have the days currently structured as a Timeline column.

Any insight or suggestions would be super helpful!

Hello @Michaela_Schwartz,

Currently, I’m not aware of any native monday.com feature that can do that. The closest solution will be to use the Date Check app to send a notification if the new date or timeline can be found in an existing timeline.
Here is a demo of similar use case.