Doesn’t Hurt to Ask Book Summary By Trey Gowdy

*This post contains affiliate links, and we may earn an affiliate commission without it ever affecting the price you pay.

Doesn't Hurt to Ask (2020) is a must-read for anyone looking to honed their persuasion skills and learn the subtle art of asking questions – whether that be in a courtroom, business meeting, or at home.

This book by former congressman Trey Gowdy will show you how you can use questions to effectively reach your audience, communicate your message, and win people over.

You'll gain valuable insight into the power of well-crafted questions and learn how to use them to create more meaningful conversations and lasting impressions.

So whether you plan to use these newfound skills professionally or in your personal life, Doesn't Hurt to Ask has got you covered!

Doesn't Hurt to Ask Book

Book Name: Doesn't Hurt to Ask (Using the Power of Questions to Communicate, Connect, and Persuade)

Author(s): Trey Gowdy

Rating: 4.3/5

Reading Time: 22 Minutes

Categories: Communication Skills

Author Bio

Trey Gowdy is an esteemed figure in the world of law and politics, making an impressive name for himself thanks to his roles as federal prosecutor, district attorney, and congressman.

He chaired the House Committee on Oversight and Government Reform and was part of the Select Committee on Benghazi after being elected to Congress in 2010.

Trey also recently collaborated with his friend Tim Scott to produce a New York Times best seller titled ‘Unified: How Our Unlikely Friendship Gives Us Hope For A Divided Country’.

This renowned author is sure to bring readers thoughtful insight in his new book, 'Doesn't Hurt To Ask', as he has had extensive experience in investigations and governmental oversight roles throughout his career.

The Power Of Asking Questions: How To Convince Anyone Of Anything With The Right Questions

Right Questions

If you want to be successful in any endeavor, it pays to be able to advocate for your beliefs.

The author of Doesn’t Hurt to Ask has the perfect method for doing that – asking questions.

Asking the right kinds of questions can be extremely powerful and effective when trying to convince someone of something.

The book teaches readers how they can use their questioning skills in all aspects of their lives, from business meetings and courtrooms, to family dinners and school assemblies.

With this book’s guidance, you’ll learn how even a silly argument can turn into a passionate speech; why a seemingly stupid question is better than a stupid answer; and when it’s okay to “flog a dead horse”!

So if you’re looking for better ways of advocating for your beliefs, this book will teach you exactly what you need to know.

Learn how to become an expert persuader with the power of questions!

The Power Of Questions: How Asking Rather Than Telling Can Win Arguments

When it comes to persuasion, subtlety is key.

Far too often, people think that if they just keep repeating their point of view, the other person will eventually be swayed.

But in reality, this is counter-productive and rarely works.

The best way to win an argument is by listening to your conversation partner and asking them the right questions.

Through powerful questioning techniques, you can effectively nudge your partner in the direction of understanding your point of view without making them feel like they’re being attacked or overwhelmed.

Natures Nutrition‘s author knows this all too well.

He only got into law school after a friend’s mom asked him a series of thoughtful questions that made him reflect on his life goals and educational path.

That’s why he advocates for subtle questioning as one of the greatest tools of persuasion – it gives us much more control over how we communicate our ideas without making someone feel defensive or misinformed.

At the same time though, it’s important to avoid asking stupid questions like “What color was the blue bag?” during a robbery trial (the answer obviously should have been blue!).

Such questions don’t contribute anything meaningful to the discussion anyway.

In summary: Once you master utilizing effective questioning techniques for persuasion, you’ll find that getting people to understand and agree with your point of view becomes much easier!

Know Your Objectives, Facts, And Jury To Master The Art Of Real-Life Persuasion

If you want to succeed in any kind of debate or conversation, it is essential to be aware of your objective, know your facts, and understand who makes up your “jury”.

In a court case, for example, the prosecutor needs to convince the jury beyond reasonable doubt.

But in every day conversations, such as when discussing politics or business strategies with family members or colleagues, absolute conviction isn’t always possible.

Instead of outright trying to convince someone to change their beliefs completely, you can try to gently sway them more towards yours.

To do this effectively requires having an aim in mind beforehand and arming yourself with facts that can be used to support it.

The extent of evidence required will vary depending on what exactly you are trying to achieve.

Finally, it is important to have a good understanding of who you are talking to – the “jury” – as this will influence how you should present your argument in order for it to resonate most effectively with that particular group or individual.

Questioning them also helps you better assess whether they are even open being persuaded at all before wasting time on lengthy arguments that could fall flat.

The Right Question Can Change The Course Of A Conversation


We all use questions in different situations and contexts, but it’s important to know that different types of questions are more effective in certain scenarios.

The author of the book “Doesn’t Hurt To Ask” illustrates this by using an example from his own TV interview with President Trump: instead of simply stating his opinion on the issue at hand, the author asked “Why is our justice system more respected than our political system?”.

This question, set up the president to discuss why that is, even though the author had his own opinion on that, too.

This example just goes to show that there are two key types of questions – softball questions and hardball questions.

Softball questions are non-leading inquiries such as “Who inspired you to run for office?” which allow the questioned person plenty of room to answer as they please.

On the other hand, hardball questions typically contain a leading statement such as “Didn’t I tell you to take out the trash this morning?”, implying a yes answer before hearing one back.

But then there’s also another type of inquiry – why? The word can be used regardless if it’s a soft or hard question and it has its own effect when it comes to conversation starters and getting answers.

When asking “why?” make sure you really do want to hear an answer because once spoken, you can’t take it back!

How To Fake Sincerity In Litigation: Learning The Do’S And Don’Ts

If you want to make an impact and be truly convincing, the key is sincerity.

That means no insults, hypocrisy or lying.

You’ll earn the respect of your audience by showing that you genuinely care about your beliefs and are passionate about what you’re saying.

The importance of real emotions can’t be understated.

If you don’t show that you’re invested in your argument, people won’t take it seriously.

So if you’re trying to get a message across, make sure to convey genuine convictions with every word and action.

Even for mundane issues like dinner time with the family, try to uncover the deeper meaning behind them – like respecting others’ time and shared family values.

When you tap into those big ideas, it’s easier to talk sincerely and passionately about even the smallest of details.

When it comes down to it – if you want to be persuasive, you have to be sincere!

How To Impeach An Argument And Undermine Someone’S Credibility

Impeaching an argument by questioning the facts, logic or character of the person presenting it is a powerful strategy to use in the art of persuasion.

It can be as simple as asking your opponent how they know what they are claiming, or disputing the logic behind their argument.

If you can demonstrate that the facts or logic used is flawed, you’re one step closer to successfully impeaching their argument.

The third and most effective form of impeachment is disputing character.

This involves proving to an audience that your opponent is habitually dishonest, biased or immoral.

Furthermore, if someone your opponent has a connection to has been discredited, this could also be used as a way of dealing a blow to your opponents’ argument – referred to as “impeachment through hitchhiking”.

By skillfully implementing one of these three forms of impeachment – questioning facts, logic or character – you can greatly weaken and even completely undermine someone’s argument.

The Power Of Precision And Repetition In Argumentation: Ask Your Opponent To Clarify Their Terms, Repeat Your Point For Emphasis, And Repackage Their Argument For Maximum Effect


Persuading someone requires both finesse and a thorough understanding of the language.

In his book, “Don’t Hurt to Ask,” author Michael Bloch provides great insight into how to fine-tune your persuasion skills.

He suggests measuring your words, repeating what has been said, and repackaging your arguments if need be.

Measuring your words is essential in an effective argument or question.

You want to frame it in a way that can not be challenged or misinterpreted.

Simple and precise wording is best when trying to convince somebody of something – using big, generalized terms like ‘always’ or ‘never’ are asking for a rebuttal from the other person.

Repetition also contends as an important factor in persuading someone.

Your audience will take more notice if you repeat yourself—not to mention, give them time to process the information properly.

In fact, with enough repetition, jurors may have already heard enough evidence against the guilty party even before all the facts are presented!

And finally, it doesn’t hurt to consider repackaging if your argument isn’t making headway.

Reduce it down to absurdity by expressing it differently – often times this will really highlight the invalidity of the initial statement.

With these tactics in mind, you’ll be well on your way to mastering persuasive conversations!

Four Strategies To Save Yourself When Your Argument Is Failing: Prevention, Divert, Deconstruct, Double-Down, And Play The Victim

If your argument isn’t going the way you’d like it to, don’t panic.

With a few savvy strategies, you can still save yourself from backing yourself into an argumentative corner.

The trick is to diversify and break down your opponent’s arguments, double down on the facts that work in your favor, and play the victim card if all else fails.

The best strategy of all is prevention – have a good sense of your weaknesses before jumping into the fray so you don’t end up in an awkward situation.

Spend just as much time preparing and padding your weakest points as you spend defending your strongest.

If something isn’t going as planned, redirect the conversation with questions that steer the focus onto your opponent, challenge their assumptions with statements such as “how do you know that?”, or lean hard on facts that are working for you.

And if all else fails, there’s always sympathy for a victim – present yourself as unfairly attacked by putting your feeling into words.

All these strategies should help you get out of most tricky arguments and hopefully even win them!

The Art Of Persuasion: How To Convince Others By Setting The Right Expectations And Staying Open

Right Expectations

Learning the art of persuasion is an invaluable skill that can help you in many aspects of life.

To become a master of persuasion, it is important to understand the importance of setting realistic expectations and staying open to different perspectives.

In his book Doesn’t Hurt to Ask, author Patrick Leigh explains how he tested the persuasive abilities of young lawyers that he was recruiting for positions by giving them five minutes to convince him to go see their favorite movie.

Although these young law professionals initially had great difficulty with this task, they got better over time as they practiced on actual cases in court.

In order to be successful when engaging in persuasive conversations, it is important to take a step back and remember not to pressure your opponents into adopting your point of view.

Instead, gently guide them towards coming up with their own conclusion by making thoughtful inquiries and giving them space until they reach a logical decision on their own.

It’s like leading a person to water—you can never make them drink.

Finally, if you wish to successfully persuade somebody else, you need stay open-minded yourself.

You must remain receptive to alternative facts and views and be willing re-evaluate your beliefs when presented with contradictory evidence.

This way, you’ll build a trustworthy reputation for yourself which will help you carry out effective conversations in the future as well.

Wrap Up

The Doesn’t Hurt to Ask book by Amanda Lannert is packed full of actionable advice on how to use questions to persuade people and win arguments.

By carefully choosing the facts you include and the questions you ask, you can bypass people’s defenses and get them on your side.

The author’s final summary point is this: start with your best fact when you’re asking questions.

That way, you can make a powerful impression right away and back it up with other relevant information throughout your argument.

Additionally, save your second-best fact for your last question as a climactic capstone to reinforce all of your points.

With these tips in mind, go forth and ask questions confidently!

Arturo Miller

Hi, I am Arturo Miller, the Chief Editor of this blog. I'm a passionate reader, learner and blogger. Motivated by the desire to help others reach their fullest potential, I draw from my own experiences and insights to curate blogs.

Leave a Comment

This site uses Akismet to reduce spam. Learn how your comment data is processed.