How to Test Negative for Stupid: And Why Washington Never Will

Gather initial thoughts and broad opinions about the book.

1. How did you react to John Kennedy’s distinctive voice and plain-spoken style? Did you find his use of humor, analogies, and sharp-edged commentary to be effective and engaging, or did it sometimes feel distracting?

2. Kennedy frames his story as that of a populist outsider, even with his elite education and long career in government. To what extent did you find this “insider-as-outsider” persona convincing?

3. What was your main takeaway from the book? Do you feel it succeeded more as a personal memoir, a critique of Washington, or a political manifesto for a specific kind of governance?

Encourage readers to connect the book’s themes and characters with their personal experiences.

1. Kennedy’s political brand is built on candor, which he argues is a necessary tool for accountability. Thinking about your own professional or personal life, when have you found direct, blunt communication to be most effective? Are there times when a different approach might work better?

2. Have you ever found yourself in a new environment, like Kennedy in Washington, where the culture felt completely different from your own? How did you navigate the unwritten rules and expectations?

3. Kennedy recounts a formative high school experience confronting a bully, from which he learned that “weakness invites the wolves.” How do you feel about this philosophy? Is projecting strength always the best way to handle conflict in your own life?

4. One of the book’s key moral tests occurs when Kennedy refuses Edwin Edwards’s offer to be placed on a “sample ballot” for cash, a decision he believes cost him an election. Think about a time you faced a choice between an easier path that compromised your values and a more difficult one that felt right. What guided your decision?

5. The book details Kennedy’s decision to volunteer as a substitute teacher to understand the challenges of public education firsthand. What is the value of leaders seeking out this kind of ground-level experience instead of relying on reports and experts?

6. During his response to Hurricane Katrina, Kennedy defied FEMA rules to ensure evacuees were not separated from their pets. Can you think of a time when you felt it was necessary to bend a rule or challenge a bureaucratic process to do the right thing?

Examine the book’s relevance to societal issues, historical events, or cultural themes.

1. The theme of a Populist Revolt Against Elites is central to the memoir. In what ways do you see this tension between “the establishment” and “ordinary people” playing out in society today, whether in politics, media, or culture?

2. Kennedy argues that the mainstream media has become a partisan subsidiary of the DC establishment, abandoning objectivity to pursue a political agenda. How does this portrayal align with or challenge your own view of the media’s role in shaping public discourse today?

3. In Chapter 9, Kennedy presents himself as an advocate for restoring legitimacy to the Department of Justice. What do you see as the broader societal risks when major institutions like the justice system are widely perceived as being politicized?

Dive into the book’s structure, characters, themes, and symbolism.

1. Throughout the book, Kennedy presents a central paradox: He’s an Oxford-educated intellectual who speaks with the folksy wisdom of a small-town Louisianan. How does he manage this tension in his writing? Did you find this combination of personas to be authentic?

2. The memoir’s structure shifts from a chronological narrative to a policy “Speed Round.” What impact did this shift away from narrative and toward declarative writing have on your reading experience? Why do you think Kennedy chose to end the book this way?

3. The memoir uses figures like Donald Trump and Joe Biden as narrative foils. In what ways do Kennedy’s portrayals of these two presidents help to define his own political identity and philosophy?

4. The guide suggests that many of Kennedy’s stories are structured as parables with clear moral lessons. Discuss one of these stories, such as his confrontation with David Duke or his battle over the C-band spectrum auction. What specific lesson about politics or leadership do you think the story is designed to teach?

5. Kennedy explains his 2007 switch from the Democratic to the Republican party by arguing that the parties had shifted, not him. How does this explanation compare to similar justifications made by other political figures who have switched parties, such as Ronald Reagan’s famous statement, “I didn’t leave the Democratic Party. The party left me”?

Encourage imaginative and creative connections to the book.

1. So much of Kennedy’s political identity is tied to his memorable one-liners. If you were tasked with writing a few Kennedy-style zingers for a current political debate, what issue would you choose, and what analogy or sharp-witted phrase would you create?

2. Imagine you had to create a “Field Guide to Washington DC” based on Kennedy’s descriptions in the book. What would you name the “five families” of the establishment, and what would be your top survival tip for a newcomer?

3. The title, How to Test Negative for Stupid, implies a common-sense test for politics. If you were to design a similar three-question “common sense” test for another field you know well, like your job or a hobby, what questions would you ask?