Reassign all objects when deactivating a user

Once again, I am manually reassigning over 500 tasks from someone who is suddenly no longer with the company to their backfill. When I deactivate a user, a message should pop up "This person is assigned to XX work, would you like to reassign these to a different user?"" If yes, then a reassignment button pops up and I enter a name. If no, then all open objects will be closed or canceled. If not sure, then tasks will remain assigned to the person and I have the option to go back to this account at some point and reassign.

This single activity is a huge time suck that should take less than a minute.