Hi Lori, these are my comments:
For Direct Manager is best if you use "Jefe Directo". The word "Jefe" suits better because "Direct Manager" means "your immediate authority" and we use "Jefe" to express authorithy at any level.
For Hotel Manager: "Administrador del Hotel", the word "Administrador" suits better than "Gerente" because it is an stablisment, you usually translate "Chief Excecutive" as "Gerente"
I would translate each question as:
¿Quién es tu jefe directo?
¿Quién es el Administrador del Hotel?
¿Quién es la Asistente del Administrador del Hotel?
¿Quién es tu supervisor? o ¿Quién es el supervisor?
In the case of "Direct manager" I think it can only be a direct question and that's why "tu" is mandatory.