I think that you want the workflow to continually check those values. To do that would require WF to be in an endless loop and it will not allow that.
Supposing the current hiring manager changes, then their workflows will sit in the task list until a controller re-assigns them. If you use a Role for the hiring manager instead of an explicit user combined with the task overdue re-assignment function then the task will go to the new hiring manager when it becomes overdue.
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