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14 min 40 sec
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Doesn’t Hurt to Ask: Using the Power of Questions to Communicate, Connect, and Persuade

Shows how to persuade at work and at home by asking questions instead of making speeches. Drawing on his years as a prosecutor and congressman, Gowdy covers everything from setting realistic goals to rescuing an argument that is slipping.

Table of Content

If your usual way of winning someone over is to pile on facts and opinions, you have probably watched people dig in instead of coming around. In Doesn’t Hurt to Ask, former federal prosecutor and congressman Trey Gowdy argues for a better tool: the question. A good question keeps the focus on the other person and lets them reach your conclusion themselves, so there is nothing to defend against. Gowdy sharpened the skill in courtrooms and congressional hearings, but he insists it works just as well in a meeting, a classroom or at a family holiday dinner.

His case is that persuasion means gently guiding people, and that prepared, well-chosen questions guide them better than any speech. Along the way come a realistic target for any argument, a question for each moment, and ways to stay credible, expose a weak case and recover when yours slips.

A young man headed for construction work after high school came out of a talk with a friend’s mother planning a career in law, and she never once told him what to do. The method behind that conversation works on almost anyone.

A prosecutor needs near certainty to win. Everyone else is playing a different game, and setting the bar too high is one of the surest ways to lose an argument you could have won.

Some questions invite a long, open answer and others leave room for only one reply. One small word sits in a category of its own, and it can turn a whole story upside down.

A trial lawyer was once told that the trick of the job is faking sincerity. Gowdy thinks that advice is half wrong, and the half that is right works even for squabbles about dinner time.

An argument can look solid and still rest on hearsay, a leap in reasoning or a source nobody should trust. Gowdy illustrates two of these routes with his own questioning, including of a former head of the FBI.

A casual question on a golf course fell apart under three follow-ups, and a murder trial turned on a phrase the jury heard again and again. Precision and repetition matter more than most people expect.

Even skilled persuaders get backed into a corner. Gowdy keeps four exits ready, from a well-timed interruption to a move he admits is undignified but still works, as one famous exchange showed.

When Gowdy was a district attorney hiring young trial lawyers, he gave every candidate the same test: five minutes to convince him to see their favorite movie. Many of these trained professionals did badly. With practice on real cases, they got better, and that is the hopeful heart of the book. Persuasion is a skill, and it grows with use.

Gowdy also asks for honest expectations. Few people change their minds in one conversation, least of all on divisive issues like gun control or abortion. You can lead a horse to water, the saying goes, but it decides whether to drink. Your work is to bring people close enough to reach their own conclusions, remembering that everyone in a crowd hears you through their own life. It also means staying persuadable yourself, open to new facts and willing to adjust when the evidence turns, since you cannot ask of others what you refuse to do.

One habit is worth trying this week. Weave your best fact into one of your first questions, follow with your third-best, and save the second-best for the very end. Then ask, and let the other person finish the thought. The woman who sent Gowdy into law never made a single argument.

About this book

What is this book about?

Most people try to win arguments by stating their facts and opinions as forcefully as they can, and most of the time the other side digs in. Trey Gowdy spent years persuading juries as a prosecutor and questioning witnesses as a congressman. He argues that the stronger tool is the question. A good question keeps attention on the other person and lets them reach your conclusion for themselves, so they have nothing to push back against. Gowdy builds a practical method around that idea. He suggests aiming to move someone 30 to 50 percent of the way, which is realistic, instead of hoping for total agreement. He explains when to use open softball questions, when to use leading hardball ones and why the question why stands apart. He also lists the habits that destroy credibility and the three ways to take apart a weak argument. The examples come from murder trials, congressional hearings, a golf course and the family dinner table. Readers get a toolkit for meetings, negotiations and family disagreements. It includes ways to sharpen and repeat a question and to recover when an argument fails, along with a reminder to stay open to persuasion themselves.

Book Information

Rating:

Genre:

Communication & Social Skills

Topics:

Communication, Conflict Resolution, Persuasion

Publisher:

Penguin Random House

Language:

English

Narrator:

Ethan

First published:

August 18, 2020

Pages:

288

Length:

14 min 40 sec

Get the book:

Amazon

Who it's for

  • Winning debates, not minds

    Professionals who win the debate in meetings but rarely change anyone's mind.

  • Bringing others around calmly

    Managers, salespeople and founders who need colleagues, clients or investors to come around without a fight.

  • Tired of family arguments

    Anyone tired of family arguments that end with everyone more dug in than before.

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About the Author

Trey Gowdy

Trey Gowdy was a federal prosecutor in South Carolina and later district attorney for Spartanburg and Cherokee counties. He represented South Carolina's 4th district in Congress from 2011 to 2019, chairing the House Select Committee on Benghazi and the House Oversight Committee. After Congress he rejoined a law firm, became a Fox News contributor, hosted Sunday Night in America with Trey Gowdy and also hosts The Trey Gowdy Podcast. His other books include Start, Stay, or Leave, and he co-wrote Unified with Senator Tim Scott.

Ratings & Reviews

Ratings at a glance

4.3

Overall score based on 758 ratings.

What people think

Listeners find this book captivating and straightforward, praising the educational insights into the craft of asking questions to influence others. The presentation is approachable; one listener highlights the conversational delivery, while others enjoy the lighthearted, humorous moments. Listeners admire the personable feel of the content—one review specifically mentions the author’s moral compass—and find the overall message quite stimulating.

Top reviews

Hom

This book provides a masterclass in the subtle art of the query, written with the sharp precision you’d expect from a former prosecutor. Gowdy manages to strip away the complex jargon of the courtroom and present a blueprint for everyday communication that feels remarkably accessible to everyone. I appreciated his focus on the 'moral compass' of persuasion; it’s not about manipulation but about seeking truth through better questioning. While the heavy focus on legal anecdotes might slow down some readers, I found his storytelling both humorous and incredibly grounded. It’s rare to find a book that balances professional tactics with such a personable, conversational tone. Whether you are arguing a case or just trying to navigate a family dinner, the strategies here are genuinely thought-provoking and immediately applicable to real-life situations.

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Titiluck

Finally got around to finishing this, and I’m struck by how much heart Gowdy poured into these pages. It’s far more than just a list of tactics; it’s a reflection on integrity and how we treat one another through our words. Look, the guy knows how to tell a story, and his humor shines through even when he's discussing heavy topics from his prosecution days. I found the section on 'knowing your audience' to be a game-changer for my own professional presentations. It feels like you’re sitting across from a mentor having a long, meaningful conversation over coffee. It’s rare to find an instructional book that is this engaging without being dry or overly academic. Highly recommend this to anyone who wants to communicate with more purpose and a stronger moral footing.

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Palm

Ever wonder why some people always seem to get the answers they want while others struggle to be heard? This book breaks down that mystery with a mix of Southern charm and legal brilliance. Gowdy’s approach is refreshing because he doesn't just tell you to be loud; he tells you how to be strategic and thoughtful. The chapter on listening was particularly eye-opening for me. His writing style is so easy to understand that I flew through it in a single weekend. While he does get into the weeds of legal procedures, those stories serve as the perfect laboratory for his theories on persuasion. It’s an instructive, funny, and deeply personable guide that I’ve already started recommending to my colleagues who struggle with public speaking and confidence.

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Pornthip

Wow, Trey Gowdy really delivered a punchy and surprisingly funny look at how we talk to each other. I loved how he used his high-stakes career to illustrate simple points that anyone can use in their personal life. The book is incredibly easy to read and doesn't get bogged down in technicalities, despite the author's extensive legal background. His focus on using questions to uncover the truth is a much-needed perspective in today's polarized climate. It’s a thought-provoking read that leaves you feeling more equipped to handle difficult conversations with family or bosses. If you want a book that is both instructive and genuinely entertaining, this is definitely the one for you. Five stars for the humor alone!

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Pornpimon

After hearing Gowdy speak on several podcasts, I was eager to see if his writing style matched his verbal wit. To be fair, the book definitely leans more toward a memoir than a standard self-help guide on communication. He spends a lot of time recounting specific cases from his time in Congress and as a prosecutor, which is fascinating if you like law. However, I can see how some might feel he drifts too far away from the core 'how-to' advice at times. The practical takeaways regarding burden of proof and audience expectations are absolute gold, though. Even if you aren't a law nerd, his insights on how to frame a question to get to the heart of a matter are worth the price of admission. It just requires sifting through a bit of political scenery.

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Tanyaporn

As someone who works in a high-stakes corporate environment, the advice on 'asking your way to a conclusion' was surprisingly effective. Gowdy translates his trial experience into a manual for anyone who needs to move people toward a specific goal. Truth is, I expected it to be a bit more partisan given his background, but he stays focused on the mechanics of communication throughout most of the text. The prose is conversational and moves quickly, though I’ll admit some of the legal stories ran a little long for my taste. Still, the core lessons on building a case and understanding the 'bar of proof' are incredibly useful for business. It’s a solid addition to the shelf for anyone looking to sharpen their rhetorical teeth without feeling like they’re reading a textbook.

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Ten

Gotta say, the transition from the courtroom to the living room in this book is handled with a surprising amount of grace. Gowdy focuses on the 'art' of the question, which is something most of us take for granted in our daily interactions. Frankly, there were moments where the political context felt a bit heavy for a book ostensibly about communication, but he usually manages to bring it back to the central theme. The advice is practical and grounded in real-world experience rather than abstract psychology. I particularly appreciated the distinction between persuading someone and merely winning an argument. It’s a nuanced take that encourages the reader to consider their long-term relationships over short-term victories. A few sections felt slightly repetitive, but the overall message about effective inquiry is quite powerful.

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Pichaya

Picked this up after a recommendation from a friend in the legal field and I wasn't disappointed by the content. Gowdy’s conversational tone makes even the more complex ideas regarding 'the burden of proof' feel manageable and relatable for a non-lawyer. I did feel that the book was a bit heavily weighted toward his own career anecdotes, which might be a turn-off if you aren't a fan of memoirs. However, the underlying lessons on how to frame your objectives before you ever open your mouth are vital. He emphasizes the importance of a moral compass in all our interactions, which is a refreshing take in a genre often filled with manipulative tactics. It's a solid 4-star read that offers great insights into the psychology of questioning and persuasion.

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Sureerat

Not what I expected when I picked this up looking for a general guide on better conversation. The title suggests a broad look at persuasion, but in reality, it’s mostly a collection of war stories from a prosecutor’s career. Personally, I found the constant legal framing a bit exhausting because I wanted more niche secrets for everyday life rather than 'how to cross-examine your spouse.' The writing is certainly clear and Gowdy is a charismatic narrator, but the connection between his courtroom tactics and office politics felt stretched thin in several chapters. It’s a decent read for fans of the author or those interested in the legal field, but for the average person seeking communication skills, it might feel a bit too niche. A bit more editing to make it shorter would have been better.

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Krisada

In my experience, the effectiveness of a communication book relies on its ability to translate theory into practice, and this one mostly succeeds but with caveats. I’ve read a lot of books on communication, and while Gowdy is a gifted storyteller, I often felt like I was reading his autobiography rather than a guide to persuasion. If you aren't interested in the inner workings of a prosecutor's mind or the halls of Congress, you might find yourself skimming through several chapters. To be fair, his 'persuasive tools' are logically sound and very easy to follow, but they aren't necessarily revolutionary. It’s a good book, just not a great one if you’re looking for high-level rhetorical theory. It feels very much like 'How to Argue 101' for the general public, which is fine, but it didn't quite hit the mark for me.

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Questions about this book

Trey Gowdy argues that questions persuade better than statements. Questions keep the focus on the other person and let them reach your conclusion themselves, so they feel no need to defend. Drawing on his work as a prosecutor and congressman, he shows how to set a realistic goal, gather facts, read your audience, pick the right type of question, stay credible and take apart weak arguments.

Not completely. Courtrooms demand near certainty, but everyday disputes about politics, business or family values rest on opinions. Gowdy suggests that moving someone 30 to 50 percent toward your view is a reasonable goal. At that point they have started to see your side and question their own beliefs, for example by admitting you do more chores or investing a small sum in your start-up.

Softball questions are open and non-leading, built on words like who, what and when, such as asking a governor what inspired the run for office. They map the ground and show interest. Hardball questions are leading and imply their answer, such as asking whether you didn’t already say to take the trash out this morning. Gowdy puts the question why in a category of its own.

Gowdy’s first advice is to prepare your weakest points in advance. If you are still cornered, stop repeating the same approach and try one of four moves: divert by interrupting with a question, deconstruct each assumption by asking how they know, double down on your strongest fact, or, as a last resort, play the victim, as Paul Ryan did when President Obama attacked him.

It suits anyone who argues often but persuades rarely: managers, salespeople, founders pitching investors, students and people tired of family disputes. The tools are concrete, from asking whether someone is open to hearing your view, to dropping words like always and never, to ordering your facts with the strongest first and the second-strongest last.

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Doesn’t Hurt to Ask

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