Isn't there always a clash of contexts between the expert and the apprentice wanting different things?
Contexts are usually shared. There's an implicit agreement between the adversaries to make it mutual. When Donald Trump abuses the people on The Apprentice, they are agreeing to getting pressured, put down and positioned against each other. They all buy into a context of battling each other, gaining power over others, taking positions and defending their stances.
When the context of the user gets understood, isn't that compromising to the authority figure's different context?
If there is a show of making a big sacrifice, condescending to relate to the low-lifes or losing ground to handle others' concerns, there is still a shared context. There is agreement to abuse and get abused. It takes two to create suffering, who each thing it only takes the one they blame.
What's the shared context when everyone appears disheartened, bored and forced to be there?
That can be called a pity party with a punch bowl of woe and cocktail conversations about victim stories. Those with the expertise don't want to know what effects they're having, what impressions they're making or what signals they're sending to their audiences. Those who feel the effects, get the impressions and see the signals -- don't want to say anything, act like they care or proceed with self-respect. Both agree to make each other miserable, complain about it later and dread the next encounter. They share a context of "don't wanna, don't make me".
What's the point of context development if the context is already held in common and maintaining itself ad-infinitum?
There's always a default context like the default settings in word processing software for margins, fonts and displayed menus. It's possible to change the settings before beginning to deliver content. Seeing context as an opportunity to be more effective takes advantage of how the context is usually shared. Everybody wins or everybody loses. There's no escaping the agreement to be equally miserable, ambitious, considerate or collaborative. There's simply a change to something better held in common.