Is it possible to create a notification if 2 or more items in board 1 have dates in the same timeline and the name in the mirrored employee column (from board 2) match?
The only solution I have right now is to color code items in a Calendar view by that mirrored employee column.
Once these items are connected, you could set up a recipe to notify someone based on when an item is connected in the connect board column using when column changes recipe: