Being A Boss

Say an employee says she wants to make me aware of something that might be coming down the pike. She has put her son on the waiting list for a daycare center (not ours) and if he gets in she won't be able to work until closing anymore. We have openers and closers; she is our closer.

Later while in my craft room this conversation rears its head. I'm thinking wait a minute - her scheduled hours are 9:30-5:30 and just because she her sone might be attending another daycare does that mean I have to change her hours?

Could I walk in to my bosses office tomorrow and say I have to pick Maisy (my cute canine kid) up from daycare at 4 so I won't be able to work until 5:00 anymore. Does life work like that? Or is this employee expecting something that hasn't been given?

Then I think a bunch of ways to work through this situation being nice - like see if other staff want to close so she can get her son, and then it dawns on me that I need to tell her I might not be able to accomodate her request. Which I wonder, makes me too hard as a boss and then the whole tug of war starts between my need to be nice and my need to run my program.
So which side needs to win - the nicey nice or bitchy boss? And is there room for both in the land of bosshood?