I suppose, but you never actually have to tutor Derek.
It is merely an invisible barrier to advancement and one that makes limited sense for a player intent on engaging Derek: "I want Derek in the club! Let's go tutor Tamara a lot!" is not a sentiment that flows naturally. Being allowed to ask and getting told that he can't get the position unless his grades improve (and then tying it to a few effective tutoring sessions w/Derek) would remove the barrier and improve consistency in the fiction.
From a game mechanics PoV I 100% agree, it is unintuitive as hell. Baal doesn't mind seeing players flail about a bit.
From a roleplaying/in-world perspective it kinda makes sense. You're asking for a favor from someone in a position of power..... like, if you work in a McDonalds and you are asking the manager to cut some slack to your friend who keeps showing up for work late, you are more likely to be listened to if you're an outstanding employee.
Anyway, I'm not trying to defend it-- I agree, it is an unintuitive game mechanic, and ought to have some kind of in-game breadcrumb ("At least I am making progress with Tamara, maybe once I get her grades up some more I will talk to Larson"). Just saying there _is_ a rationale, however odd.