Doesn't Hurt to Ask - Book Summary

Dive into the art of question-based persuasion

Have you ever found yourself in a situation where you wanted to persuade someone to see your perspective, but despite presenting an arsenal of facts, arguments, and personal views, you failed to budge them? Maybe you were speaking with a potential employer, discussing an investment opportunity, or advocating for a cause at the Thanksgiving dinner. And it left you wondering, is there a more effective way to convince others? Turns out, there is.

Author Trey Gowdy harnessed this powerful persuasion tool as a prosecutor, and later as a congressman. This tool is none other than the art of asking questions. His expertise in using questions as a persuasive device transcended the courtroom and Congress, proving that this technique could work wonders in various scenarios — professional, academic, social, and even familial settings.

Through this narrative, you will discover the untapped potential of questions. They can be your most potent persuasive ally, helping you steer discussions in your favor. Whether your goal is landing your dream job, securing a crucial loan, or persuading your sceptical aunt about climate change — the right questions can be game-changing.

In this journey, you'll explore —

- why it's better to ask a silly question than to blurt out an ignorant response,

- how you can transform a mundane argument into a compelling conversation about freedom and justice,

- and why revisiting previously settled discussions, akin to "flogging a dead horse," might occasionally be necessary.

Master the delicate craft of persuasion using queries as your prime resource

Are you eager to emerge victorious in every debate you partake in? Do you aspire to overwhelm your opponents with your discourse skills?

If your answer is 'yes', then this narrative might not align with your expectations.

Winning an argument isn't about utterly vanquishing your opposition — it's about establishing a dialogue, understanding their perspective, and communicating your beliefs in a way that resonates with them. Reflect on this: when was the last time you were coerced into changing your viewpoint simply because someone was relentlessly imposing their opinions on you?

The secret weapon in persuasion is questions. They switch the spotlight onto your conversation partner and gently guide them towards your viewpoint without triggering a defensive stance. The author's personal experience speaks volumes here. He was inspired to pursue a law career after being bombarded with thought-provoking questions by a friend's mother.

In essence — persuasion is a delicate craft, and questions are its prime resources.

During his high-school days, the author had planned to work construction jobs post-graduation. However, during a casual conversation, his friend's mother began inquiring about his future plans. Each answer he provided led to another question. By the end of this 'interview,' he found himself wanting to be a lawyer.

The mother had not issued a single judgmental statement to steer his decision. Instead, she allowed him to arrive at the conclusion himself — a testament to the persuasive power of well-placed questions.

Before we dive deeper, let's debunk one myth: there is indeed such a thing as a stupid question. Once, during a robbery trial, the author — in response to a witness stating that the suspect had a blue bag — instinctively asked, "Okay, what color was the blue bag?" The courtroom's ensuing laughter made it evident that foolish questions do exist.

However, a stupid question still trumps a foolish assertion. Consider the disparity between someone asking you, "Who wrote Hamlet?" and someone confidently claiming, "George Washington wrote Hamlet." While the former demonstrates a lack of knowledge, the latter shows misinformation the person is oblivious to. In the realm of sincere debates, it's crucial to question — who would you trust more? An uninformed person or a misinformed one?

Understand your purpose, validate your facts, and know your audience

In a legal trial, a prosecutor must convince the jury beyond reasonable doubt, aiming for a near 100 percent conviction. Even a speck of uncertainty about the defendant's guilt could sway the verdict.

Real-life conversations are not the courtroom, though. It's often implausible to persuade someone completely, especially when dealing with subjective matters such as politics, business strategies, or personal values. These conversations are inevitably intertwined with personal opinions and ethical evaluations.

In reality, persuasion is more about gently nudging your conversation partner toward your viewpoint. To succeed in this, you must be clear about your destination, map out the route to get there, and figure out how to bring your partner along.

Therefore, keep in mind — know your objective, validate your facts, and recognize your audience.

Before you delve into an argument, understand the purpose of your discourse. While convincing someone 100 percent is rarely realistic, a 30 to 50 percent persuasion is a pragmatic target. At this point, your opposition starts acknowledging your viewpoint and begins questioning their beliefs. For instance, your spouse might admit that you shoulder more household chores, or someone might agree to a small investment in your startup.

The more quantifiable your objective, the simpler it would be to strategize your argument. So, clarity about your end-goal is paramount.

When formulating your questions to drive home a point, ensure they are grounded in facts. They should mirror the characteristic of any other argument, supported by evidence. The digital era simplifies this task, requiring nothing more than internet access and a discerning mind.

Your burden of proof corresponds directly to the magnitude of your objective. Persuading someone to invest $10,000 in your venture requires a more robust, fact-based argument compared to securing a $100 investment.

The presentation of your argument depends on your audience — be it a jury panel of twelve, a group of colleagues, or a family member. Questions assist you in understanding their beliefs, the rationale behind them, and the best way to address them. They also help you gauge your audience's openness to persuasion. A simple "Are you open to discussing this?" could potentially save you considerable time and energy!

The context determines the type of question to employ

There was an instance when the author engaged in a live TV interview with President Trump, focusing on the fairness of politics. He could have initiated the conversation with his perspective, but he chose to pose a question: "Why is our justice system more respected than our political system?"

Even without expressing his viewpoint, the author drew a comparison between the two systems and steered the President toward discussing the reasons — although he had his convictions on that matter too. The author had selected the right question for the occasion.

The essential point to remember — the type of question to employ depends on the situation.

Broadly, questions can be categorized into two types. First are the 'softball' questions. These are simple questions allowing your counterpart ample latitude to answer, without necessarily driving home a point. They are non-leading — composed of words like 'who,' 'what,' and 'when,' giving the person being questioned the freedom to steer their response. For instance, "So, governor, what inspired you to run for office?" is an apt example of a non-leading, softball question.

Softball questions facilitate defining the boundaries for the debate, communicating to your conversation partners that you value their input. They subtly guide into your argument. For instance, "Honey, when did you last take the trash out?" is a relatively harmless way to delve into a more comprehensive discussion about household chores.

Eventually, though, you'd want to pose more challenging questions that either affirm your standpoint or contradict and stall your opposition's point. This is when 'hardball' questions come into play. These are leading questions that place the emphasis on the question itself rather than the response. Think about: "Didn't I tell you to take out the trash this morning?" The question subtly implies a 'yes' response.

Questions usually fall into the hardball or softball categories. However, there's a unique category reserved for the question "why?" The power of 'why' can shift dynamics entirely. Imagine asking someone why they killed their spouse. If the response is, "because he was abusing our children," it would elicit a drastically different reaction compared to the answer, "because he was snoring." The implications are vast.

Authenticity is key in persuasion

The author once received an intriguing piece of advice on successful litigation — learn to feign sincerity. However, that statement presents a paradox. It's impossible to authentically fake sincerity, but it's possible to tap into genuine emotions, enhancing your credibility, appeal, and sincerity to your audience.

While the concept of sincerity seems easy, it's more challenging to demonstrate. However, a couple of clear dos and don'ts can navigate this course.

The vital insight to remember — sincerity is essential in persuasion.

When it comes to sincerity, several taboos exist. The first is insults. Reflect upon this — how often have you been swayed to another's viewpoint following an insult? The only outcomes of insult are heightened defensiveness and aggression, and it portrays you as petty and insecure.

The second deterrent to sincerity is hypocrisy. Subjecting your opposition to a different standard compared to yours will invite skepticism about your argument's ethical foundation.

The most detrimental factor to sincerity, however, is dishonesty. Most people are inclined to pardon a genuine mistake, but intentional manipulation of facts to deceive them is unacceptable. Once trust is shattered, your argument crumbles.

As for the dos of sincerity, winning your audience's trust involves demonstrating genuine passion for your beliefs. Authentic emotions matter because they signal your genuine care for the subject. Hence, ignite your emotions to bolster your argument. At times, this comes naturally. For instance, while pursuing a guilty verdict for a child murderer, you would undoubtedly feel a surge of strong emotions.

But what about more routine matters like ensuring your children arrive promptly for dinner?

Here, you need to identify a broader principle that you can be passionate about. Regarding punctuality for dinner, you could communicate to your children that the matter isn't merely about missing a meal or two. Instead, it pertains to them respecting your time and the shared family time. By aligning with a higher ideal — such as family values, fairness, or justice, you can demonstrate genuine passion, regardless of the issue's scale.

Discredit an argument by challenging the facts, logic, or character

We have just discussed the three primary threats to sincerity and credibility — insults, hypocrisy, and lies. These can erode your argument if wielded carelessly. However, if you can skillfully deploy these credibility killers against your adversary, they can be your greatest allies.

In a word, credibility killers can facilitate impeachment. While the term 'impeachment' might seem applicable only to a president, its interpretation here is somewhat different.

In the context of persuasion, impeachment signifies dismantling the credibility of an argument via one of three avenues. Let's explore how to achieve this.

The takeaway here — facts, logic, or character are levers for discrediting an argument.

The first method of impeaching an argument involves challenging the facts that serve as its foundation. To impeach based on facts, it could be as straightforward as questioning your opponent about the source of their information. If you can expose their 'facts' as mere conjecture, their argument suffers a massive setback.

If your adversary's facts hold water, but their conclusion radically deviates from yours, you might need to resort to the second impeachment tactic — challenging their logic. The author once utilized this strategy against Julián Castro, Obama’s secretary of Housing and Urban Development. Castro advocated for the citizenship of millions of undocumented immigrants, justifying it with the achievements of a few individuals. The author undermined Castro by highlighting that his conclusion didn't logically flow from his argument. He questioned why a few extraordinary cases should define the policy for the entire group?

The third impeachment method — character impeachment — is the most potent yet challenging. The goal here is to convince the audience that the opposition is prone to lying, holds unfavorable biases, or is morally corrupt.

At times, you can impeach someone by discrediting an associated person. This technique, known as 'hitchhiking,' is a strategy the author employed while questioning former FBI director James Comey during the investigation into the Hillary Clinton email scandal.

The author aimed to cast doubt on Clinton's credibility through Comey. Thus, he posed several questions to Comey, to which he knew the answer would be a resounding 'no.' For instance, he asked Comey if Secretary Clinton had ever emailed classified material to anyone from her government account, as she had claimed. Comey conceded that this was not accurate.

The author refrained from accusing Hillary Clinton of deceit directly, but by making Comey respond to a series of questions, he successfully cast a shadow of doubt over her credibility.

Hone your persuasive abilities through precise language, repetition, and rephrasing

During a casual golf round, the author's friend asked, "Would you agree that under the current administration, America holds more global respect than during President Obama's tenure?" The author, instead of responding directly, questioned his friend's usage of terms. What exactly did his friend mean by 'worldwide'? How did he define 'more respected'? What were the criteria for both? The friend couldn't provide a precise answer.

Quite often, we employ vague terms without considering their exact meaning. Therefore, prompting your adversary to elucidate their terms can sometimes be sufficient to expose the flaws in their argument. But bear in mind, the opponent can subject you to the same scrutiny.

The key insight here — precision in language, repetition, and rephrasing can enhance your persuasion prowess.

To defend your argument against opposition, you need to weigh your words carefully. Your questions should be straightforward and accurately worded. As a rule of thumb, it's better to avoid wide-ranging words such as 'everybody', 'always', or 'never'. They open the door for counter-questions such as "So, you're implying that I never contribute to household chores?" In such cases, a more exact and powerful question would be "Why didn't you help with emptying the dishwasher?"

Once you have meticulously crafted your question, repeat it to reinforce its importance. While repetition isn't a typically sought-after rhetorical skill, it indeed should be. The more frequently you iterate something, the more your audience will understand its significance.

During a case involving a man accused of murdering his wife, the author repeated a variant of the same question — "What did your wife say when you stabbed her the first time? What was her reaction when you stabbed her again?" By the end of the questioning, the jury had heard the phrase "when you stabbed your wife" so many times that it didn't require much more to convince them of his guilt.

If you find it challenging to undermine an opponent's argument, consider rephrasing it. Rephrasing involves reducing an argument to absurdity by presenting it in alternate words. The author often applied this strategy when advocating for victims of domestic violence. When the defense attorney insinuated that the woman should have been prudent enough not to return to her abusive partner, the author would distort this statement to its extreme — "Are you implying that she deserved the abuse?"

When your argument falters, use tactics like diversion, dismantling, reinforcing, or playing the injured party

Persuasion is an art form, and even its most proficient practitioners occasionally falter. There will be instances where you might need to accept defeat and withdraw gracefully. However, several approaches can help minimize the repercussions of a failed argument.

Prevention, as they say, is the best cure. Avoid painting yourself into a corner by familiarizing yourself with your weaknesses. As you build your argument, you might be drawn towards its stronger aspects. Nevertheless, it's equally important to fortify your argument's weakest segments, rather than hoping they won't be challenged.

If your argument still unravels despite your preparations, a few last-ditch strategies might come to your rescue.

The core idea here is — when your argument is floundering, diversion, deconstruction, doubling-down, or playing the victim can be effective strategies.

An old adage says, "When you find yourself in a hole, stop digging." This wisdom is as relevant to the art of persuasion as it is to any other endeavor. If you're cornered during an argument, don't persist with your previous line of argumentation. Instead, you need to mitigate your losses.

The first strategy you can employ is diversion. Typically, people don't appreciate being interrupted. However, if you interrupt with purposeful questions, you could halt their momentum and redirect the conversation while ensuring they remain the focus.

The second strategy is deconstruction. If your opponent is attempting to construct a robust argument, try challenging each minor assumption they put forth. Queries such as "How do you know that?" and "Are you certain about this?" can effectively slow down your adversary.

The third tactic is inspired by another popular saying: "There's no point in beating a dead horse. But then, it certainly won't hurt either." If there's a fact or argument that particularly strengthens your case, don't hesitate to reinforce it. Actually, you can keep emphasizing this point until you figure out a way to escape the argument.

If all else fails, you could resort to the fourth strategy: playing the victim card. Though it might not be the most dignified move, it's effective because people are innately sympathetic towards victims. During the debate surrounding the Affordable Care Act, former Speaker of the House, Paul Ryan, employed this tactic when President Obama accused him of being less concerned about children's welfare. Ryan countered with a series of questions emphasizing the unfairness of Obama's attack, one being, "How do you think your misrepresentation of my faith and spiritual beliefs affects me?"

Becoming a persuasive communicator involves setting reasonable expectations and maintaining an open mind

While serving as a district attorney, the author had the opportunity to guide numerous young lawyers. But before they were hired, they had to prove their persuasive abilities with a straightforward task: within five minutes, convince the author to watch their favorite movie.

Surprisingly, many budding legal professionals struggled with this seemingly simple task. However, the silver lining was that they improved their persuasion skills over time by practicing in actual court cases.

You already possess the skills needed to defend your beliefs with purposeful questioning. With dedication and practice, these skills can be refined. But there are a few crucial reminders to consider as you progress.

The essential lesson here is — becoming a persuasive communicator involves setting reasonable expectations and maintaining an open mind.

Persuasion is not about victory, but effective communication. To succeed, you must set realistic expectations.

Think about this — how often have you seen someone's opinion change as a result of a single conversation? Likely not often, especially when it concerns contentious issues such as gun control or abortion. Therefore, it's unwise to overstretch your goals. Otherwise, you're just paving the way for disappointment.

As the old saying goes, "You can lead a horse to water, but you can't make it drink." Your goal in persuasion should not be to coerce your listeners to concur with everything you articulate. Instead, it should be to guide them towards forming their own conclusions based on your argument's merits.

That is the essence of persuasion. Questions are an effective tool for subtly guiding your audience in the right direction, but ultimately, they must complete the final steps of convincing themselves. Always remember, every individual has a unique way of processing information — even when you're addressing a large group. So, always strive to appeal to each audience member by relating to their real-life experiences.

One last important note to remember during your journey: to persuade others, you must also be open to persuasion. This means being receptive to new facts and viewpoints and adjusting your beliefs when faced with contradicting evidence. After all, if you're unwilling to alter your mindset in response to a compelling argument, you can't expect others to do so either.

Concluding Thoughts

The central idea of this narrative is:

The art of persuasion is rooted in the strategic use of questions. By understanding your goals, identifying the facts pertinent to your argument, and knowing your audience, asking the right questions can help you sidestep resistance and secure their agreement. The power of questions allows you to reinforce essential points, highlight flaws in an opponent's argument, and guide people to arrive at their own conclusions that align with your stance.