Doesn’t Hurt To Ask Summary

1-Sentence-Summary: Doesn’t Hurt To Ask teaches persuasion via asking the right questions, explaining that intentional questions are the key to sharing your ideas, connecting with your audience, and convincing people both in the office and at home.

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Doesn't Hurt To Ask Summary

Trey Gowdy is a former Congressman and Prosecutor, and he knows firsthand how difficult it can be to persuade people to see things the way you do. 

In Doesn’t Hurt to Ask: Using the Power of Questions to Communicate, Connect, and Persuade, Gowdy uses his experience to teach the subtle art of persuasion through asking questions. Good questions can win people over. 

No matter what setting you find yourself in, whether you’re in the boardroom or at family dinner, you can nudge people in the right direction by asking the right questions.

These are 3 of the best lessons the book teaches:

  1. Asking questions is the key to the subtle art of persuasion. 
  2. You can strengthen your argument by measuring your words, repeating yourself, and repackaging your opponent’s claims. 
  3. If you need to cut your losses in an argument, divert, deconstruct, double-down, and play the victim. 

Ready to discover the art of persuasion? Let’s get right into it!

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Lesson 1: One of your most valuable tools for persuading someone else is learning how to ask good questions.

Effective persuasion isn’t just about being good at debating with your opponent. It is about listening, communicating, and sharing your beliefs in a way that is compelling.

Questions are a great way to persuade others because they place the focus on the conversation with the other person and are good at avoiding defensive responses. The author himself only got into law after his friend’s mother asked him a series of good questions.

Gowdy wanted to get into construction, but one day his friend’s mom asked what he was going to do. Then, she asked a follow-up question. And another one. And more after that. By the time he was done talking to her, he decided he actually wanted to be a lawyer. 

The funny thing is, his friend’s mom didn’t even want to persuade him. She let him persuade himself. That, Gowdy says, is the power of asking questions. 

The author does clarify, however, that there is such a thing as a stupid question. For example, once during a robbery trial, Gowdy’s witness described a suspect with a blue bag in his hand. Immediately after, the author asked, “Okay, what color was the blue bag?” The laughter that followed that day can back up the notion that there is such a thing as a dumb question. 

Still, the author believes that a stupid question is better than a stupid assertion. Typically, someone would trust a person who is uninformed before a person who is misinformed.

Lesson 2: You can improve your persuasion skills when you measure, repeat, and repackage.

“Do you agree America is more respected worldwide now than under President Obama?” someone asked Gowdy. Gowdy asked for more explanation: What does “more respected” mean? How do you define “worldwide?” His friend had no answers.

Far too often, people use vague or imprecise terms they can’t really define when it comes down to it. This is why asking an opponent to clarify can tear holes in their argument. However, they can also do the same to you. 

Questions you ask should be both simple and precise. First, avoid generalizing words like “everyone,” “never,” or “always.” These lead the way to rebuttals like, “Right, so you think I never pick up after myself?” 

Next, use repetition to drive your point home. The more you repeat something, the more your audience will begin to understand its importance. 

When questioning a man accused of murdering his wife, Gowdy asked the same question in different ways over and over. He asked, “What did she say after you stabbed her the first time? What did she say when you stabbed her the second time?” By the time he finished, the jury had heard “when you stabbed your wife” so many times, they were convinced the man was guilty.

Lastly, if you find yourself struggling to defeat your opponent’s argument, try repackaging it. This is when you make an argument suddenly sound absurd by putting it in different words. 

The author would use this strategy when he worked with domestic violence victims. If someone on the defense suggested that the woman should have known not to return to an abusive situation, he would twist this by asking, “So you’re saying it’s her fault she was abused?”

Lesson 3: If you are losing your argument, try to divert, deconstruct, double-down, or play the victim in response.

The author knows that even masters of persuasion can’t always nail an argument. Sometimes the best thing to do is walk away. But he does have a few last-second strategies to mitigate the damage from a failed argument. 

The first thing the author says you can do is to try to make a diversion. People dislike being interrupted, but if you can interrupt them with questions, you may be able to hinder their momentum and turn the conversation in another direction, all while staying focused on them.

Next, you can try to deconstruct. When your opponent is nailing their argument, you can challenge even the smallest of their assumptions to slow them down. Ask things like, “How can you know that?” or “How can you really be sure that’s true?” 

The third strategy is doubling down. If one part of your argument is working particularly well, double down on that point until you can find a way to get out of the argument. 

If all of this fails, your last strategy to save yourself is to play the victim card. Sure, this doesn’t seem very dignified. But it works for a simple reason— people are naturally more empathetic to victims. 

For example, when former House Speaker Paul Ryan was attacked during a debate over the Affordable Care Act, Obama claimed Ryan didn’t care about children. Ryan capitalized on this by playing the victim and highlighting the unfairness of Obama’s attack.

Doesn’t Hurt To Ask Review

I always love reading books about communication because they remind me of all the awesome people I know who are mind-bendingly good at it. Doesn’t Hurt To Ask has to be one of my favorite books on this subject because of how detailed it is. I think everybody is going to benefit from this, whether they work in a career that requires persuasion or not!

Who would I recommend the Doesn’t Hurt To Ask Summary to?

The 54-year-old with strong political beliefs that wants to be able to share them without feeling icky, the 35-year-old parents who are at a loss for how to persuade their kids to do the right things, and anyone that wants to be a better communicator in all walks of life.

Last Updated on June 14, 2023

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Luke Rowley

With over 450 summaries that he contributed to Four Minute Books, first as a part-time writer, then as our full-time Managing Editor until late 2021, Luke is our second-most prolific writer. He's also a professional, licensed engineer, working in the solar industry. Next to his day job, he also runs Goal Engineering, a website dedicated to achieving your goals with a unique, 4-4-4 system. Luke is also a husband, father, 75 Hard finisher, and lover of the outdoors. He lives in Utah with his wife and 3 kids.