
Doesn't Hurt to Ask
10 minUsing the Power of Questions to Communicate, Connect, Persuade, and Lead
Introduction
Narrator: A ten-year-old girl named Meah Weidner, who had cerebral palsy and was confined to a wheelchair, was dead. Her mother’s boyfriend, a firefighter and EMT, claimed it was a tragic accident. He said she had a seizure, fell from her wheelchair, and that he may have inadvertently harmed her while performing CPR. The case landed on the desk of prosecutor Trey Gowdy just weeks before he was set to leave for Congress. He could have passed it on, but he felt a profound duty. For the little girl who could no longer speak, he would talk. For the girl who couldn’t defend herself, he would defend her. In the courtroom, Gowdy didn’t rely on shouting or theatrics. Instead, he used logic, facts, and a series of relentless questions to dismantle the defendant’s story, guiding the jury to see the truth for themselves. The jury found the man guilty, and he was sentenced to life in prison.
This high-stakes world of the courtroom, where persuasion determines justice, forms the foundation of Trey Gowdy’s book, Doesn't Hurt to Ask. He argues that the skills used to advocate for the most vulnerable are not confined to legal battles. They are universal tools that can be used to communicate, connect, and lead in every aspect of life, from the boardroom to the dinner table. The book is a masterclass in the art of persuasion, built not on making statements, but on asking the right questions.
Persuasion Begins with Purposeful Preparation
Key Insight 1
Narrator: Before one can ever hope to persuade another person, Gowdy argues that the most critical work is internal. Persuasion is not an impromptu performance; it is a deliberate act that requires rigorous preparation. This involves asking a series of self-directed questions: What is my ultimate objective? What facts must I master to make my case? Who is my audience, or "jury," and what do they believe? And finally, how difficult will it be to prove my point?
Gowdy illustrates the transformative power of this principle not with a courtroom drama, but with a quiet, life-altering conversation from his own past. In the summer after college, a young Gowdy was aimless, considering a job in construction. His best friend's mother, Mrs. Cox, saw a different potential in him. One morning, she asked him to stay behind while the others went to the beach. She didn't lecture him or tell him what to do. Instead, she asked a series of gentle, guiding questions about his future, his dreams, and what he thought others expected of him. She had a clear objective: to help him see a higher path for himself. She understood her audience—a young man full of pride and potential. By asking questions, she allowed Gowdy to arrive at his own conclusion. She ended by telling him, "Surprise the skeptics, Trey, and do something amazing in life." That single, well-prepared conversation set him on the path to law school. It demonstrates that effective persuasion is rarely about winning an argument; it's about understanding your goal and your audience so thoroughly that you can help them find their own way to the truth.
The Art of Advocacy is Wielding Questions, Not Just Arguments
Key Insight 2
Narrator: The central thesis of Gowdy’s book is a fundamental shift in how we view influence. True persuasion is not about overwhelming someone with the force of your argument. It is the subtle art of guiding them to a conclusion through strategic inquiry. Gowdy contrasts his experience in the courtroom with his time in Congress to make this point. In a courtroom, the jury is expected to be a blank slate, open to being persuaded by the evidence presented. In politics, however, he found that most people arrive with their minds already made up, making genuine persuasion nearly impossible. You cannot move someone who is unwilling to be moved.
The key, therefore, is to use questions to open a mind that might otherwise be closed. A declarative statement invites a defensive response or a counter-argument. A question, on the other hand, invites reflection and participation. It forces the other person to engage with the facts and logic on their own terms. As Gowdy demonstrates in the Meah Weidner case, his role was not to tell the jury the defendant was a liar. His role was to ask questions that exposed the inconsistencies in the defendant's story, allowing the jurors to conclude for themselves that he was lying. This method is more powerful because the conclusion feels like a personal discovery to the person being persuaded, rather than a belief being forced upon them.
Master the Tools of Inquiry: Corroborate, Contradict, and Impeach
Key Insight 3
Narrator: Once you accept that questions are your primary tool, the next step is to understand what kind of questions to use and why. Gowdy breaks this down into a prosecutor's toolkit, applicable to any persuasive scenario. Questions generally serve one of two purposes: to corroborate your position or to contradict the other person's. Corroborating questions build your case, adding layers of evidence and reinforcing your core message. Contradictory questions are designed to undermine the opposition's argument by highlighting flaws, inconsistencies, or a lack of evidence.
Beyond this, Gowdy introduces the legal concept of "impeachment." This isn't about political removal from office, but about discrediting a witness or their testimony. He outlines three ways to do this. You can impeach the facts, proving that the information someone is using is just plain wrong. You can impeach the conclusion, showing that even if their facts are right, the conclusion they draw from them is illogical. Or, you can impeach the person, demonstrating that they have a bias, a motive to lie, or a history of untrustworthiness that makes their entire testimony suspect. By understanding these different modes of questioning, a persuader can move from simply asking questions to strategically deploying them to build their own case while systematically dismantling the alternative.
Authenticity is the Unbeatable Closing Argument
Key Insight 4
Narrator: For all the techniques and strategies, Gowdy insists that the single most powerful tool of persuasion is authenticity. Sincerity cannot be effectively faked. People have an innate sense for what is genuine, and credibility is the currency of persuasion. If your audience doesn't believe you, they will never believe your argument, no matter how logical it is.
He shares a deeply personal story about this principle in the book's acknowledgments, directed at his wife, Terri. He describes her as having mastered the art of persuasion not through debate, but by leading an authentic life wholly dedicated to her beliefs. As a prosecutor trained in cross-examination, Gowdy admits, "I have never won an argument with or successfully cross-examined an authentically lived life." Her unwavering kindness, humility, and faith are more persuasive than any argument he could ever construct. This illustrates a profound truth: the foundation of all persuasion is trust. Before you can move someone to your position, they must first believe in your integrity. Techniques are useful, but they are hollow without a bedrock of genuine conviction.
Redefine Success: Aim for Movement, Not Total Victory
Key Insight 5
Narrator: In a world of polarized debates, it's easy to think of persuasion as an all-or-nothing battle. You either win the other person over completely, or you fail. Gowdy argues this is a flawed and counterproductive mindset. The goal of persuasion is often not total conversion, but incremental movement. Success might mean moving someone from being hostile to being neutral. It might mean getting them to acknowledge a single valid point in your argument. Or it might simply be finding a small patch of common ground where none existed before.
He stresses the importance of setting realistic expectations. If you are trying to persuade someone on a deeply held belief, the burden of proof is immense, and the likelihood of a complete reversal is low. Instead of aiming for an impossible victory, aim for progress. By seeking to understand the other person's perspective and looking for areas of potential agreement, you can build a bridge rather than a wall. This approach transforms persuasion from a confrontational act into a collaborative one. It's not about winning; it's about connecting and moving people—even if it's just one small step at a time—closer to understanding.
Conclusion
Narrator: Ultimately, Doesn't Hurt to Ask delivers a powerful and counterintuitive message: the path to effective persuasion is paved with humility, not hubris. The book’s single most important takeaway is that true influence comes from empowering others to find the truth for themselves. It is the art of asking questions that illuminate, rather than making statements that demand. Trey Gowdy dismantles the idea of the persuader as a charismatic orator and rebuilds it as a thoughtful, empathetic guide who uses inquiry to lead others toward a new perspective.
This reframes communication not as a battle to be won, but as a puzzle to be solved together. The challenge the book leaves us with is a simple one: in your next conversation, your next meeting, or your next disagreement, resist the urge to declare your truth. Instead, ask a question. Don't just advocate for your position; seek to understand theirs. You may not win every argument, but you will build understanding, and in doing so, you will have mastered the subtle, and far more powerful, art of persuasion.