The Swiss Army knife is presented as a symbol of both practical resourcefulness and institutional threat. In what sense are these two different ways of viewing the knife guided by two different visions of the relationship between individuals and their communities? Does the novel endorse one of these views over the other?

What are the multiple meanings of the novel’s title? How does the title contribute to the story’s overall meaning?

How does the disrepair of Wolf’s Eye Middle School impact different characters in different ways? What do their reactions reveal about the characters?

How does Jackson’s character help reveal what is most valued at WEMS before Dexter arrives? How does the novel demonstrate that the values of the school have genuinely changed by the end of the novel?

What is a “fish-out-of-water” story? How is Dexter typical of the protagonist of such a story? How does this trope help structure the action of Old School?

To what extent does Old School advocate for a hybrid model of education by presenting both the strengths and weaknesses of Dexter’s unconventional upbringing at The Pines? How does the unique setting of The Pines either strengthen or weaken this argument?

How does the activity of codebreaking relate to Dexter’s experiences at WEMS? How does the nature of the code that Dexter develops for the school board meeting relate to the meaning of “codebreaking” in this story?

Trace Gianna’s development from an ambitious reporter using Dexter for a story to a loyal friend and activist. How does her journey explore the ethical responsibilities of journalism and storytelling, and in what ways does her character represent a middle ground between Dexter’s sincerity and Jackson’s cynicism?