This is a preview of the Shortform book summary of Doesn't Hurt to Ask by Trey Gowdy.
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In Doesn’t Hurt to Ask, former prosecutor and South Carolina politician Trey Gowdy draws on his professional experience to provide strategies for persuasion and argumentation. He advises focusing on facts and hard evidence, listening to and showing respect for your conversation partner, and above all, asking questions. While having persuasive skills can help you advance your goals, Gowdy also believes that it can make you better at connecting and collaborating with other people. He argues that this skill is sorely needed in the US right now: He left politics in part over his frustration with a deeply partisan Congress in which most people were already entrenched in their position and not open to debate.

(Shortform note: Gowdy served in Congress during an extremely partisan time in American politics, with many voters viewing collaboration between the two parties post-2016 as unlikely to impossible. While not a moderate himself, Gowdy repeatedly came under fire from fellow Republicans for his criticisms of then-President Donald Trump. Beyond Doesn’t Hurt to Ask, he’s had to defend his relationships with moderates like Tim Scott and even some Democrats in interviews, arguing that cross-party activity is necessary for political change.)

Gowdy mainly **draws on his experiences as a...

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Doesn't Hurt to Ask Summary The Goal of Persuasion

Gowdy argues that the goal of persuasion shouldn’t simply be to advance your own point of view, but to better understand others and reach a higher truth through debate. He repeatedly emphasizes that persuasion is not about winning for its own sake, but about convincingly presenting what you believe to be the truth to others. The truth is more important than the benefits of winning, and to that end, Gowdy believes that you should always enter a debate with an open mind and the willingness to be convinced of your opponent’s point of view.

(Shortform note: Gowdy’s high-minded approach to persuasion stands in contrast to many other guides, which are more Machiavellian in their suggestions of how to use persuasion to succeed personally, professionally, or financially. For example, books like All Marketers Are Liars by Seth Godin and Negotiation Genius by Deepak Malhotra and Max H. Bazerman encourage the use of persuasive techniques to more effectively sell a product or promote a business. On the...

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Doesn't Hurt to Ask Summary Know Your Material

Moving from the goals of persuasion to tactics, Gowdy believes that you should enter a debate armed with as much knowledge as possible about both your topic and your opponent. Preparedness matters more to success in rhetoric than charisma or luck and can be more reliably honed through practice. While you should strive to appear confident and likable to your opponent and (if applicable) your audience, Gowdy argues that it’s more important to appear credible—if your knowledge can be trusted, then your interpretation of that knowledge and the conclusions you draw from it naturally appear more legitimate.

(Shortform note: In contrast to Gowdy’s focus on knowledge over charisma, Scott Adams argues in Win Bigly that charisma is all that matters. Examining Donald Trump’s rise to power in 2016, Adams notes that Trump’s lack of political experience and frequent factual errors didn’t diminish his popularity, but actually increased it. Trump voters valued the way he made them feel—[angry but...

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Doesn't Hurt to Ask Summary Ask Questions

According to Gowdy, the most effective tool of persuasion isn’t any particular way of making an argument, but asking questions. Asking questions serves three main functions: It endears you to your opponent or audience by showing that you’re an active and engaged listener; it allows you to learn about your opponent’s beliefs, evidence, and reasoning; and it allows you to guide the flow of the conversation without appearing to do so—by asking leading questions rather than making declarative statements. Gowdy claims that as a prosecutor and chair of Congressional committees, he spent more time asking questions than constructing a narrative from those answers.

(Shortform note: Gowdy’s emphasis on asking questions makes sense given his background—while lawyers are given the opportunity to make speeches in US courtrooms, namely during their opening and closing arguments, much of their time is spent questioning witnesses and posing rhetorical questions to the jury. Similarly, [Congressional investigative...

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Shortform Exercise: Use Questions in Persuasion

Gowdy believes that an important part of persuasion is listening to the other person and asking questions about their position. This not only makes you a better persuader, but also makes agreement and future collaboration more likely.


Consider an argument or debate you’ve had with someone recently. What was your position? What was your opponent’s position?

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