It's really interesting to look at the difference between Kurt's mentor Isabelle Wright and Blaine's mentor June Dolloway; Isabelle immediately finds personal Ohio connections with Kurt and confesses her insecurities, she's looking for someone to reignite her artistic side and feels a little crushed by the restrictions of management -- she sees herself in Kurt except he does have better organizational/assertive skills than she does, so there's kind of an aunt-and-nephew vibe to them, the lightly scattered fairy godmother to his clearly-defined goals and style. She throws open the door to a world of high fashion and kikis and access to things that Kurt's been dreaming of and sewing up in solitude since he was a wee little thing, and she ushers him through gently and as a friend-boss. Which is great because Kurt's due a kind-hearted person who understands his interests and talents to encourage him, who can help him chart his New York course.
June establishes herself off the bat as someone to be appealed to and wooed for the power that she holds -- which is also social and career capital, so long as Blaine toes the line and understands that he's her protege and he represents her in everything he does. Which is his bailiwick to begin with! Blaine's input into his work with June is probably nowhere near Kurt's with Isabelle and (especially at that point) that's what he needs, anyhow, is a firm hand and clear, direct guidance. June's leeway where Blaine's concerned is about his performance charisma and his ability to charm people, because she doesn't have to worry much about him succeeding at those things, and in turn she provides him a safety net, a foundation, and lbr a figure of ultimate authority -- though one he can push back against if it's important enough to him, which June can appreciate (within reason) because Blaine's biddable otherwise.
There's definitely overlap, they're probably both getting taken to those lunches at Indochine and wherever, but while Kurt and Isabelle's would be breezy and chatty like intergenerational workplace pals where career and socializing intermingle freely because they love both things equally, June and Blaine's would be more like Aunt March and Amy from Little Women lol -- the powerful dowager with her attentive and eager-to-learn companion who'll be rewarded with a trip to Europe to hobnob with important people. I just really love that they both had these relationships with these older women, in ways that were specific to what each of them needed for their personality styles. (There's something a touch darker about June's mentorship vs Isabelle's, which I think is also fitting for them, but that's something for fic rather than meta heh)
