A few things. I filled a late summer gap for a school year when I was there, as I had a very specialized background Hockaday needed to teach a particular class.
First--all schools have their internal dramas and soap operas, but this place has significantly more intense "whispering around the copy machine" than most. Cultural.
Second--as gleaned from self-same whispering around the copy machine--the school is well-known for telling potential hires what they want to hear during the hiring process in terms of teaching assignments and such, but feels no particular compunction to fulfill what they had previously represented. I experienced it myself. Be warned. If you think you will have an AP section or something like that because Hockaday brass told you such was their intent, don't bank on it.
Third is something particular to my area, history and social studies, but may exemplify a more general problem. There is a unresolved cultural clash between teachers who (1) approach the pedagogy of young woman not much different than Hockaday did in, say, 1970; and (2) teachers who want to help young women fully engage in the modern world.
Case in point. Hockaday offers NO advanced AP or Honors level classes in Government or Politics, despite considerable student hunger for the same. None. To the contrary, the history department discourages teachers from delving into contemporary political issues in classes for fear of stoking controversies. But sure, girls can take electives about the Romanovs; the "History of Film"; or "Breaking the Glass Ceiling: Entrepreneurship." (Why the last two are "history" classes is anyone's guess.] There is a tame-by-design middle school level "Government" class for sophomores that includes a required "social impact project," most of which elide difficult issues. Candidly, the thrust seems more to be to prepare young women to fund-raise for "worthy causes" someday as Highland Park wives than to maybe run for office or become political leaders themselves.
Nor is there a single course at Hockaday with a focus on women's history. Weird.
I write this as a male teacher. The Hockaday School does not seem to be a place to teach if you want to help women learn to be true leaders. Indeed, some of the most reactionary faculty members in this regard are women. I could not tell where admin stands on any of this.