Asking questions is both a central theme and a rhetorical tool throughout William Deresiewicz’s speech. The difference between answering questions and formulating them is key to the author’s definition of leadership. Likewise, grappling with tough questions is identified as essential to learning to think independently. Deresiewicz’s personal use of interrogative sentences both illustrates and stimulates this process. 

Deresiewicz challenges conventional ideas of leadership, such as those that equate it with bureaucratic success. The “hoop jumping” required for entry into an elite university or advancement in a bureaucracy involves giving correct answers to questions. While the author acknowledges this practice as key to hierarchical maneuvering, he differentiates it from both leadership and real thinking. He contrasts managers, who can sustain routines but not question them, with leaders, who can formulate questions and have the courage to answer them. Deresiewicz explains that reassessing and challenging old ways of doing things lead to original ideas and new paths. General David Petraeus’s story of reevaluating his superiors’ strategies and creating a new field manual exemplifies this relationship between asking questions and leadership.

Deresiewicz argues that asking questions is not merely the mark of a true leader but also an essential step in becoming one, and he acknowledges that it can be difficult.