
Doesn't Hurt to Ask
Using the Power of Questions to Communicate, Connect, and Persuade
Categories
Business, Nonfiction, Self Help, Psychology, Communication, Leadership, Politics, Audiobook, Personal Development, Law
Content Type
Book
Binding
Kindle Edition
Year
2020
Publisher
Forum Books
Language
English
ASIN
B084GBT41F
ISBN
0593138929
ISBN13
9780593138922
File Download
PDF | EPUB
Doesn't Hurt to Ask Plot Summary
Synopsis
Introduction
Have you ever found yourself in a situation where you desperately needed to convince someone of something important, yet felt completely powerless to do so? Perhaps it was a crucial business negotiation, a heated family discussion, or even a simple conversation with a friend that somehow turned contentious. In these moments, we often resort to stating our position louder or more forcefully, believing that if we just explain ourselves one more time, others will finally see our point of view. The truth is that persuasion isn't about overpowering others with arguments or facts. It's about movement—subtle, incremental shifts that bring people closer to understanding your perspective. At its core, persuasion is an art form that relies not on declarations but on questions—asking the right questions, at the right time, in the right way. This approach transforms confrontation into conversation and creates pathways for genuine connection and influence. Throughout these pages, you'll discover how mastering this subtle art can revolutionize your ability to communicate effectively in every area of your life.
Chapter 1: Know Your Objective and Audience
Persuasion begins long before you open your mouth. The most effective communicators understand that preparation is the foundation of influence. Before attempting to persuade anyone of anything, you must first clarify exactly what you're trying to accomplish. Are you seeking to change someone's mind completely, or merely open them to considering a different perspective? Are you trying to motivate action, build consensus, or simply plant seeds for future consideration? Consider Dana Satterfield's murder case. As a prosecutor preparing for this high-profile trial, I spent nearly a year immersed in every detail of the investigation. Dana was a beautiful young mother and wife who operated a hair salon from her mobile home. She was found murdered—partially disrobed and staged to be hanging from a water heater. The case had gone unsolved for a decade until DNA evidence linked a suspect named Jonathan Vick to the crime scene. But numerous challenges remained: explaining why Vick's DNA was present but his fingerprints weren't, accounting for unmatched hairs found on the victim, and overcoming a note in the lead detective's file stating "Jonathan Vick did not commit this murder." During preparation, I sacrificed family time, even taking case files to the beach during vacation. While my children played in the sand with their mother, I pored over crime scene photos, searching for answers. I examined every potential defense strategy and prepared responses. I anticipated every question jurors might have and developed answers. This wasn't just professional thoroughness—it was personal. I worked tirelessly because I believed Dana deserved someone who would fight for justice on her behalf with every tool available. When the trial finally came, the jury returned a guilty verdict in less than thirty minutes. Some might suggest this quick decision meant my year of preparation was unnecessary. I believe the opposite—the jury needed so little time precisely because I had spent a year anticipating every question, addressing every potential doubt, and creating a narrative that made the truth unmistakably clear. This principle applies far beyond courtrooms. Whether you're making a business presentation, having a difficult conversation with a teenager, or discussing politics with friends, knowing your objective with crystal clarity is essential. Ask yourself: What exactly am I trying to accomplish? What would success look like in this interaction? How will I know if I've achieved my goal? Without these answers, you're simply talking without purpose. Remember that chance favors the prepared mind. Rarely does persuasion "just happen." Life rewards preparation, and while it doesn't guarantee success, it's the single best way to hedge your bets against failure. Know your objective, know your audience, and know exactly what you're asking for—this foundation makes everything else possible.
Chapter 2: Master the Facts Before Speaking
Facts are the building blocks of persuasion. They provide the foundation upon which all effective communication is built. A fact is something that actually exists and has an objective reality. Sometimes facts can be proven; sometimes they cannot be (which is frustrating but nonetheless true). A fact that cannot be proven impacts your ability to persuade but does not diminish the existence of that fact. I learned this lesson vividly during my prosecution of the Dana Satterfield murder case. For hours, I studied crime scene photos, looking for something—anything—that would explain the presence of unidentified hairs on Dana's body that didn't match our suspect. This detail threatened to undermine our entire case. Then I saw it: photographs from the bathroom floor showed single strands of hair near the door. Not hair clippings you'd expect in a salon, but pubic hairs you might find in a public restroom. The realization hit me—Dana had been dragged across that bathroom floor to the water heater, and those hairs had stuck to her body during the process. They weren't from the killer; they were environmental contamination. This factual insight was crucial to overcoming a potentially devastating defense argument. Command of facts doesn't mean simply memorizing information. It means understanding the relationships between facts, recognizing their significance, and anticipating how they might be interpreted or challenged. It means separating fact from belief, fact from opinion, fact from theory, and fact from feeling. All of these elements are essential components of life, but facts are the single most important foundational element for constructing a winning argument. Our generation has few excuses not to gather facts. Information is available instantly on our phones. Gone are the days of periodically updating encyclopedia collections or waiting for monthly trips to the library. We have immediate access to firsthand accounts from subject matter experts. Facts have never been easier to find. The challenge lies in discerning what is truly factual from what is not, but investing time to separate truth from fiction is not a steep price to pay if your goal is to communicate effectively. Often in life, two people can look at precisely the same set of facts and draw completely different conclusions. That's precisely why we need to cultivate the art of persuasion. If we all looked at the same reservoir of facts and drew the same conclusions, we would likely not be a divided family, community, or country. There is a difference between gathering information and effectively communicating that information. We all know people who are experts on specific subjects but couldn't persuade us to come indoors during a thunderstorm. Before you engage in any persuasive conversation, ask yourself: What do I know? How do I know it? What are the limits of my knowledge? This process will help you identify gaps in your understanding and prepare you to address challenges to your position. The most persuasive people aren't necessarily those with the most facts, but those who understand their facts most thoroughly and can present them most effectively.
Chapter 3: Calibrate Your Burden of Proof
Imagine walking into a grocery store on a Saturday afternoon when someone approaches you and asks, "Do you have a second?" What does "second" make you think? Easy question, easy answer, right? But what if after you say "sure," they launch into a complex philosophical question about the origin of evil? Or perhaps they ask if you would mind attending their family reunion—in Nebraska? These requests aren't synchronized with reality. The burden of convincing someone to stop for "a second" in the grocery store and discuss the origin of evil or attend a family reunion a thousand miles away is incredibly high. This illustrates a fundamental principle of persuasion: the calibration between what you're asking for and the amount of evidence needed to convince someone to agree. As a general rule, the smaller the ask, the smaller the amount of facts and persuasion necessary; but the greater the ask—the greater the attempt to persuade or move someone from one position to another—the greater the quantum of proof and convincing required. Sheria Akins Clarke, an attorney I worked with in Congress, mastered this principle in an unusual way. She would intentionally misalign her requests with my expectations. "Trey, I have a really huge favor to ask. I'll understand if you cannot do it. I wish I did not even have to ask. I don't have anywhere else to turn," she would begin dramatically. This introduction would lead me to expect something monumental—perhaps babysitting her three children for a month while she vacationed. But then she would simply ask, "Can I borrow a pen? Mine stopped working." The predicate she laid was so out of sync with the request that I was relieved at how small it was and granted it immediately. This approach created a broader effect. I became conditioned to say "yes" when she asked for something. Being a good steward of smaller requests made her, at least in my mind, someone who could be trusted on larger asks. It's similar to what my father did when I was young. If he borrowed something, he returned it in better shape than he found it. If he borrowed someone's truck, he left it cleaner and with more gasoline than when he received it. People who demonstrate genuine appreciation for what they're asking for are more likely to get the answer they want. To understand this principle more clearly, consider the sliding scale of burden of proof used in our justice system. What does it take for an officer to stop someone on the street and ask a question? Not much—officers are free to approach citizens. What about asking a motorist for permission to search their car? Again, very little evidence is required to ask, because the driver can say "no." What about arresting someone or obtaining a search warrant? That requires "probable cause"—more than a hunch but less than 50 percent certainty. In civil cases, the standard is "preponderance of evidence"—essentially 50.1 percent certainty. For criminal convictions, it's "beyond a reasonable doubt"—about 95 percent certainty. In your persuasive conversations, be mindful of this calibration. If you're trying to convince a co-worker to eat Italian rather than Mexican for lunch, a preponderance of evidence will suffice. If you're asking someone to switch jobs or move across the country, you'll need clear and convincing evidence. If you're discussing matters of deep conviction or life-altering decisions, you'll need something approaching beyond a reasonable doubt. Remember that the burden of proof can change during a conversation. Something that seems trivial to you may be supremely important to the person with whom you're communicating. By listening and watching, you can sense when you need more evidence and adjust accordingly. The key is to match your level of proof to the significance of what you're asking for.
Chapter 4: Use Questions to Corroborate or Contradict
In September 2019, I unexpectedly found myself in the Oval Office during a conversation between President Trump and media representatives about fairness, completeness, and objectivity in reporting. When suddenly asked to weigh in, I didn't state my opinion. Instead, I asked questions: "Why is our justice system more respected than our political system? Why is there something called a rule of completeness in our justice system? If it's enough for that system we respect, why not try it with other institutions?" These weren't information-gathering questions. They were designed to frame the issues in a specific way and make points without directly stating them. When it comes to persuasion, questions serve only two objectives: they either corroborate (build up your position) or contradict (tear down opposing positions). Consider how this works in a courtroom. When a prosecutor questions a witness who previously lied to police, they might ask, "Why did you lie to the police when they interviewed you the first time?" This question acknowledges the negative fact but allows the witness to explain, potentially making them more credible. When the defense attorney asks the same witness, "Why did you lie when you talked with the police the second time?" they're trying to impeach the witness and make their testimony less believable. It's the same question—"Why did you lie?"—but with two different expectations and objectives. In the Oval Office scenario, my questions about the "rule of completeness" in our justice system were designed to make a point: that the justice system is more respected than politics or media because completeness, and therefore fairness, is embedded in the system. I used the example of saying "Mick pulled a gun on me" without mentioning "I pulled a gun on him first" to illustrate how factual statements can still be unfair when they lack context. This approach works in everyday conversations too. When discussing controversial topics like immigration or gun control, questions can help you make points without triggering defensive reactions. Instead of declaring "We need stricter gun laws," you might ask, "Are you arguing there is not a single law that could be passed to lower the risk of future mass killings?" This shifts the burden to the other person while making your point implicitly. Questions also allow you to control the conversation's direction. In a courtroom, attorneys use "softball" questions to help friendly witnesses make important points and "hardball" questions to challenge opposing witnesses. The same approach works in daily life. With allies, ask questions that give them opportunities to expound on points that support your position. With opponents, ask questions that expose weaknesses in their reasoning. Remember that questions can be more powerful than statements because they engage the other person in the persuasion process. When someone answers your question, they're actively participating in reaching the conclusion you want them to reach. They're persuading themselves, which is far more effective than you trying to persuade them directly. As you practice this approach, listen carefully to responses and let your next question flow naturally from what you hear. The most effective persuaders are often the best listeners.
Chapter 5: Build Credibility Through Authenticity
"The secret to being a good communicator, Trey, is sincerity. Once you learn to fake that, there is nothing you cannot do." This advice from David Stephens, one of the best litigators I've ever seen, contains both wisdom and irony. You cannot "fake" sincerity, of course, but the message is clear: if you don't believe what you're saying, no one else will either. Authenticity is the foundation of credibility. David Stephens was effective in the courtroom because juries believed him, judges trusted him, and defense counsel respected him. He wasn't trying to be someone he wasn't—he was simply himself, fully invested in what he was communicating. I witnessed the power of authenticity firsthand in what might seem like an insignificant case. An elementary school principal came to my office about a disturbing school case involving an assistant principal who had been accused of striking a child. The case had been tried once before with a hung jury, and objectively, it wasn't worth retrying—it was a minor offense that wouldn't result in jail time even with a conviction. But when I met the assistant principal, her authenticity changed my mind. You could not listen to this woman for any length of time without concluding she was exactly the kind of person you would want teaching your own child. Kind, gentle, nurturing, and unable to process how someone could accuse her of striking a child. Her sincerity moved me to take the case personally and retry it. During the trial, the assistant principal cried while testifying. So did I. She cried because she had been accused of the most insidious, destructive thing an educator could be accused of—hurting a child. I cried because I had encountered a type of purity of spirit not often seen. The defendant was convicted, not because of clever legal tactics, but because the jury recognized authenticity when they saw it. Authenticity can motivate people to do things they never would have considered otherwise. I went from refusing to take a minor case to handling it personally—all because someone's genuine character persuaded me that something more important than my time was at stake. When emotion is real, it is powerful. When emotion is contrived, it is destructive. We've all witnessed "crocodile tears"—fake displays of emotion that repel rather than persuade. The key is to find something you can genuinely be passionate about, even if it's not the specific topic at hand. If you're discussing a seemingly mundane issue, connect it to a larger principle or value that truly matters to you. Beyond authenticity, engagement is crucial. Make eye contact. Use welcoming body language. Listen actively and ask thoughtful follow-up questions. Even when you're not feeling particularly passionate about a topic, you can still demonstrate respect for the other person through your attentiveness. Remember that credibility killers abound: lying (intentionally deceiving), making false statements (even unintentionally), insulting others, and displaying hypocrisy. Avoid these at all costs. Instead, focus on building trust through consistency, honesty, and genuine interest in others' perspectives. As Luis Gutiérrez, a progressive former congressman from Illinois, wisely observed: "People will vote for you if they do not like you; they will never vote for you if they think you do not like them."
Chapter 6: Repackage Arguments Strategically
My father routinely received golf balls as gifts from his patients but wouldn't play them because they were "too nice to play." That made no sense to me. How can a golf ball be too nice to play? That's what it was created for! Nevertheless, he would stash his Titleist golf balls in his home office, which was off-limits to my sisters and me. Each year, Titleist would release balls with slightly different packaging—designed to be more eye-catching or highlight some technological advance. But the ball inside was essentially the same. This illustrates a powerful persuasion technique: repackaging. It makes something feel new and fresh, and it's also a devastating way to reframe your opponent's words and switch the burden of persuasion. Many of us do this reflexively in everyday conversations: "Honey, dinner is ready!" "Okay, I'll be right there." "I guess you didn't realize I have been working on it for hours?" "Umm...I said I'll be right there!" "Well, if it's too much trouble to come now, I'll just put it in the refrigerator!" It's instinctive, snarky, and persuasive—taking an "I'll be right there" and turning it into an "I'm not valuing what you've worked hard on all evening." Repackaging is especially effective when coupled with hyperbole, absurdity, and illogical extremes. It involves taking some small part of what was said and reframing it in the most extreme way. During a congressional hearing on immigration, advocates were highlighting the achievements of DACA recipients as an argument for a path to citizenship. A strategic repackaging might be: "But surely you are not arguing all fourteen million were valedictorians?" This forces the other side to acknowledge nuance in their position. This technique is common in courtrooms. In domestic violence or sexual assault cases, defense attorneys often subtly blame victims for their circumstances. A prosecutor can repackage this implication: "Are you suggesting it was her fault she was victimized? Are you saying she is not entitled to access the home without being attacked?" This exposes the underlying assumption and forces the defense to backtrack. Repackaging works because it forces the other person to defend against an extreme version of their position. Sentences that begin with "Is what I hear you saying..." or "Surely you are not arguing..." are usually repackaging something the other person said but perhaps did not mean. This technique is particularly effective in parental conversations with teenagers. When asked to clean their room, a teen might respond: "You're right, I don't ever do anything the way you want me to! I am a total failure. You probably wish you had never had me." The temptation is to retreat and begin listing all their wonderful qualities. Resist this! Instead, calmly note: "I have set aside all day tomorrow to discuss all of your wonderful qualities. I am simply hoping I can add cleaning up your room on time to that list." This keeps the focus small—please clean your room—rather than expanding into a decades-long analysis of your relationship. Remember that specificity is your friend. The more specific your original comment, the harder it is for others to repackage it into something you didn't mean. Conversely, when others make broad statements, you can use repackaging to highlight inconsistencies or absurdities in their position. Just be careful not to be too extreme in your reframing, or you risk appearing unreasonable yourself.
Chapter 7: Recognize When You've Succeeded
How do you know when you've mastered the art of persuasion? When does that moment arrive? For me, it happened somewhere between my tenth and fifteenth trial as a prosecutor. During my first ten trials, I dreaded the moment when the judge would finish giving instructions to the jury and turn to me to begin. My heart would race, my breathing would quicken, and anxiety would take over. Then something changed. Suddenly, I couldn't wait for those instructions to end because the judge was the only thing standing between me and the jury. I was eager to begin. I experienced a similar transformation with television appearances. My first live interview with Megyn Kelly was so nerve-wracking that I stared at my shoes the entire time. Now, I hate introductions when I speak because whoever is introducing me is standing between me and my desire to communicate with the audience. I can't wait for the event to start. This shift from fear to eagerness is one clear sign that you're developing mastery. Successful communicators aren't born—they develop through a painful growth process that eventually gives way to confidence and peace. This peace comes from being prepared and knowing exactly what you want to accomplish. When I hired young litigators at the solicitor's office, I would have them practice persuasion in a low-stakes environment. I'd ask them to convince me to see their favorite movie. The jury was easy (just me), the objective was clear (get me to see a movie), and the burden of proof was low (not asking for a major commitment). Many struggled initially, but almost all improved with practice and understanding of persuasive principles. Beyond eagerness, another sign of success is the ability to get results without explicitly asking for them. When you've mastered persuasion, you can present facts, express authenticity, calibrate your burden of proof, and employ questions so effectively that your objective becomes clear to everyone listening without you having to state it directly. I rarely asked jurors to convict defendants in my opening statements—how could I? They hadn't heard any evidence yet. Instead, I laid out the facts and framework so clearly that the conclusion became inevitable. You'll also know you've succeeded when contrary positions no longer threaten or irritate you. They represent opportunities, not challenges—openings for dialogue rather than invitations to argue. As I often tell people who ask how I handle political disagreements: "Contrary positions, beliefs, or convictions do not offend me. They represent both an opportunity to learn and an opportunity to persuade." Perhaps the most meaningful measure of success is when you can take someone to the brink of change and then watch as they take the final step themselves. This happened in my last murder case as a prosecutor, involving a man named Marion Lindsey who killed his estranged wife, Nell, in the parking lot of a police station while she was on the phone with 911. During my closing argument in the sentencing phase, I never explicitly asked the jury to impose the death penalty. Instead, I walked them through the concepts of mercy and vengeance, positioning justice as the middle ground: "I stand in the middle of mercy and vengeance. On a rock called Justice. And from this rock you can see the full panoply of this crime... I stand on a rock called Justice and say that taking another's life does not always mean you forfeit your own, but sometimes it does. Sometimes it does. Sometimes it does." The jury understood. They reached their own conclusion without me having to state it explicitly. That's the essence of masterful persuasion—guiding others to a destination they reach of their own accord.
Summary
Throughout these pages, we've explored how persuasion is fundamentally about movement—subtle, incremental shifts that bring people closer to understanding your perspective. We've discovered that the most effective persuasion often comes not through declarative statements but through questions that allow others to reach conclusions themselves. As I often remind myself: "Persuading those who do not agree with you—even persuasion at the margins—is where the excitement and the challenge lie. And the most effective, longest-lasting form of persuasion is when you take the other person to the brink of change, incremental or otherwise, and watch as that person takes the final step." The tools are now in your hands. You understand the mechanics of persuasion—knowing your objective and audience, mastering facts, calibrating your burden of proof, using questions strategically, building credibility through authenticity, and recognizing when you've succeeded. Now, you need only the courage to apply them. Don't wait for someone else to communicate what matters to you. Equip yourself with facts and knowledge, allow yourself to be persuaded by better arguments, and then go be the change you wish to see. Persuasion is hard, but everything in life worth doing is hard. Your voice matters—use it wisely and effectively to move others toward understanding, connection, and positive change.
Best Quote
“Getting someone to do something they were not planning on doing. Convincing someone to buy into something they never knew they were looking for. That is persuasion.” ― Trey Gowdy, Doesn't Hurt to Ask: Using the Power of Questions to Communicate, Connect, and Persuade
Review Summary
Strengths: The reviewer appreciates the author's good-natured style and tone, noting that Gowdy can be an effective communicator. Weaknesses: The reviewer found the book frustrating, mentioning that the connection between persuasion and the cases discussed in the book was not always clear. They also found it challenging to see how the different parts of the book fit together. Overall: The reviewer seems to have mixed feelings about the book, leaning towards a neutral stance. They suggest that the book may not be the best recommendation for someone looking to improve their persuasion skills unless they have a specific interest in the author's background and experiences.
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Doesn't Hurt to Ask
By Trey Gowdy