Learn how to advocate for your beliefs by asking questions.

When you’re trying to convince someone of something, you likely often take the route of stating the facts, arguments, and opinions that corroborate your belief. But there is a better way. A much more powerful tool of persuasion: asking questions. 

Asking the right questions doesn’t just work in court or Congress. It’s a skill that can serve all of us, whether it be in the boardroom, at school, or during a family Thanksgiving dinner. By learning how to nudge others in your direction, you can increase your argumentative power in almost every area of your private and professional life.

Whether you’re trying to convince someone to give you a job, a loan, or a second chance, these content will teach you how to harness the power of questions.

We’ll learn

why a stupid question is better than a stupid answer;

how you can turn any silly argument into a passionate speech on freedom and justice; and

why you should occasionally “flog a dead horse.”

Persuasion is a subtle art, and questions are its greatest tools.

Are you ready to start winning every argument you ever have? Are you ready to grind your opponents into the ground with your debating skills?

Then this is not for you.

Persuasion isn’t about annihilating your opponents. It’s about listening to them, communicating with them, and advocating for your own beliefs in a compelling way. Think about it: how many times have you changed your mind because someone kept bombarding you with their opinions?

Questions work so well because they put the focus on your conversation partner, and nudge them in the right direction without making them react defensively.

A person had always planned to work construction jobs with a friend when he’d finished high school. One day though, his friend’s mom picked up on the topic. She asked him, “What are you going to do next, honey?” After he answered, she asked a follow-up question. And then another one. And another one. By the end of the interview, he had decided that he wanted to become a lawyer.

His friend’s mother didn’t make a single evaluative statement to persuade him – she simply let him persuade himself. That’s the power of asking questions.

Now, let’s make one thing clear before you get started: there is such a thing as a stupid question. One time during a robbery trial, a witness reported that the suspect “had a blue bag in his hand.” The lawyer immediately fired off a follow-up question: “Okay, what color was the blue bag?” The laughter that ensued in the courtroom should be proof enough that stupid questions do exist.

Still, any stupid question is better than a stupid assertion. Imagine someone asking you, “Who wrote Hamlet?” That question reveals a pretty big knowledge gap. But now imagine someone telling you, “George Washington wrote Hamlet.” That’s not just a knowledge gap; that’s a knowledge gap the person isn’t even aware of. Who would you trust more in an honest debate – a person who is uninformed, or a person who is misinformed?

Know your objective, your facts, and your jury.

In a court case, the prosecutor needs to convince the jury to almost 100 percent. If there’s even a little bit of doubt about the defendant’s guilt, there likely won’t be a conviction.

In real life, though, it’s nearly impossible to convince someone beyond a doubt – and that’s especially true when it comes to topics like politics, business strategy, or family values, which almost always involve opinions and value judgments.

Real-life persuasion is more about gently moving your conversation partner closer toward your own beliefs. For that to happen, you need to know where you’re going, how to get there, and how to take them with you.

Before you start arguing with people, you need to know what it is you’re trying to achieve with your argument. Convincing someone 100 percent, as we’ve seen, isn’t usually a realistic objective.

But convincing people 30 to 50 percent is a reasonable goalpost. At 30 to 50 percent, your opponent has begun to see your point and is already challenging some of his own beliefs. At this point, for example, your spouse might have acknowledged that you do more chores than him. Or someone might have agreed to invest a small sum in your start-up. 

The more clearly measurable you make your objective, the easier it’ll be to plan out your argument. So make sure you know exactly what you’re trying to achieve.

If you want to use questions to make a point, they need to be based on facts, just like any other argument. This means you'll have to gather evidence that supports your point. With the internet and a critical mind at your disposal, this shouldn’t be too much of a problem.

Your burden of proof will depend on how lofty your objective is. Getting someone to invest $10,000 in your business, for example, requires more fact-based arguments than getting them to invest $100.

As for how you present your argument, that will depend on your jury – whether that’s 12 people on a courtroom bench, a bunch of coworkers, or a family member. Questions can help you understand what they believe and why they believe it – and how you can best talk about it. They can also help you gauge whether your jury is open to being persuaded at all. A simple “Are you open to hearing about this?” can save you a lot of wasted breath!

Different types of questions work in different situations.

He once found himself in a live TV interview with President Trump on the topic of fairness in politics. He could have started by simply stating his opinion on the issue at hand. But instead he asked, “Why is our justice system more respected than our political system?”

Without stating his opinion outright, he still made a comparison between the two systems. And he set up the president on a path to discussing why that is – even though he had his own opinion on that, too. He had chosen the right question, at the right time.

Generally speaking, there are two big categories of questions. First, we have softball questions. Softball questions are easy questions that give your counterpart lots of room to answer and typically don’t aim at making a point. They are non-leading, meaning they include words like who, what, and when, allowing the questioned person to guide the direction of their answer. A good example of a non-leading, softball question is: “So, governor, what inspired you to run for office?”

Softball questions can help you map out the ground for the debate. They show your conversation partners that you’re interested in what they have to say, and can lead into your argument in a neutral way. For example, “Honey, when did you last take the trash out?” is a pretty inoffensive way to start a broader conversation on household duties.

Sooner or later though, you’ll want to ask harder questions that help you either confirm your point, or slow down and contradict your opponent's point. This is where hardball questions come in. These are leading questions that put the focus on the question itself rather than the answer. Consider the question: “Didn’t I tell you to take out the trash this morning?” The question itself already implies the answer is yes.

Most questions are either hard- or softball. But there’s another question that’s in a category all of its own. That’s the question “why?” Why can change everything. Just consider if you asked someone why they killed their husband. How would you react if they said, “because he was abusing our children”? What if instead they said, “because he was snoring”? The difference is monumental.

To be convincing, be sincere.

He was once told that the secret to being a successful litigator is learning to fake sincerity.

Now, that’s a bit of a paradox. You can’t really fake being sincere. But you can draw on real emotions that will make you seem more genuine, credible, and likable to your audience.

Showing sincerity is easier said than done. Luckily, there are some simple dos, and a few crucial don'ts that will guide you along the way.

The first no-go when it comes to sincerity is insults. Think about it: How often have you come around to someone’s side after they insulted you? All insults achieve is making the other side defensive and aggressive, and making you come across as petty and insecure.

The second sincerity killer is hypocrisy. Holding your opponent to a different standard than your own will call the moral basis of your argument into question.

But the third sincerity killer is by far the worst – lying. Most people are willing to forgive an honest mistake. But they won’t forgive someone who intentionally twists the facts to mislead them. And once you’ve lost the trust of your audience, you’ve lost your argument.

What about the dos of sincerity? To win your audience’s trust, you need to show that you’re genuinely passionate about your beliefs. Genuine emotions are so important because they show your audience that you really care. So try and get emotional about the point you’re trying to get across. Sometimes, this will be easy. If you’re trying to convict a man who murdered a child, for example, you’ll probably be full of deep emotions.

But how does it work for more mundane issues, like getting your kids to show up for dinner on time?

What you’ll need to do is find a bigger principle to get passionate about. In the case of dinner time, you could make your kids understand that the issue isn’t really about them missing a meal or two; it’s about them not respecting your time, and your shared time as a family. If you can latch onto a higher ideal, like family values, fairness, or justice, you can get sincerely passionate about the smallest of issues.

Impeach an argument by questioning someone’s facts, logic, or character.

There are three main killers of sincerity and credibility: insults, hypocrisy, and lying. If you’re not careful, they can easily destroy your argument. But if you know how to use credibility killers against your opponent, they can work wonders for you.

Credibility killers, in a word, can help you impeach. Now, you might only have heard the term impeachment when referring to a president. But here the word has a different meaning.

In persuasion, impeachment means killing the credibility of someone’s argument via one of three routes. Let’s learn how.

The first way to impeach someone’s argument is by disputing the facts they’re basing their argument on. Impeachment via facts can be as simple as asking your opponent how he’s come to know what he’s claiming. If you can show that his so-called “facts” are really just hearsay, his argument suffers a huge blow.

If your opponent’s facts are correct, but she still reaches a completely different conclusion than you, you may have to use the second method of impeachment: disputing her logic. The same was once used against Julián Castro, Obama’s secretary of Housing and Urban Development. Castro was arguing the case for granting millions of undocumented immigrants citizenship on the basis of the achievements of some of them. But Castro was undercut by pointing out that his conclusion didn’t logically follow from his argument. Why, he was asked, should a few exceptional cases determine the policy for the whole group?

The third form of impeachment is the most effective but also the hardest. This is impeachment of character. Ideally, you’re trying to prove to an audience that your opponent is habitually lying, unfavorably biased, or morally corrupt.

Sometimes, you can even impeach someone by impeaching a person they’re connected with. This is called hitchhiking, and it’s a strategy used when questioning former FBI director James Comey during the investigation into the Hillary Clinton email scandal.

Clinton’s credibility was called into question via Comey. So several questions were asked knowing Comey had to answer with a definite no. For example, he was asked if it was true that Secretary Clinton had never emailed classified material to anyone from her government account, as she had claimed. Comey had to admit that this wasn’t true.

Hillary Clinton wasn't accused of lying, but by making Comey answer question after question like this, he succeeded in calling her credibility into doubt.

Fine-tune your persuasion skills by measuring, repeating, and repackaging.

“Do you agree America is more respected worldwide now than under President Obama?” A friend once asked  this during a round of political gossip.

Instead of answering the question, my friend was asked  to define his terms. He asked, What does “worldwide” mean in this case? What does “more respected” mean? And where is the cut-off for either? My friend didn’t have an answer.

Too often, people use imprecise terms that they aren’t prepared to define. That’s why asking your opponent to clarify her terms can sometimes be enough to tear holes in her argument. But remember, your opponent can also do the same to you.

To seal your questions against attack, you need to measure your words. Your questions should be worded simply and precisely. For starters, it’s rarely a good idea to use big, generalizing words like everybody, always, or never. They invite rebuttals like “So you’re claiming I never do any chores?” In this case, a more precise and effective question would be “Why didn’t you unload the dishwasher?”

Once you’ve finely crafted your question, use repetition to drive it home. Repeating ourselves isn’t a rhetorical skill we usually strive for – but we should. Because the more you repeat something, the more your audience will understand how important it is.

A man was questioned who was accused of stabbing his own wife to death. The  strategy was to ask him a different version of the same question over and over: “What did your wife say after you stabbed her the first time? What did she say when you stabbed her the second time?” By the end, the jury had heard the phrase “when you stabbed your wife” so many times that it didn’t take much more to convince them of his guilt.

If you’re struggling to take down an opponent’s argument, you can try repackaging it. Repackaging is when you reduce an argument to absurdity by putting it in different words. Strategy is often used when advocating for victims of domestic violence. If a defense attorney suggested a woman should have known better than to go back to her abusive partner, the statement would have been twisted  to the extreme: “So you’re saying it’s her fault she was abused?”

If your argument is failing, divert, deconstruct, double-down, or play the victim.

Even if you’re a master of persuasion, you can’t always nail it. Sometimes, you’ll just have to cut your losses and walk away. But there are a few strategies that can help you mitigate the damage of a failed argument.

The best cure, as always, is prevention. You can avoid backing yourself into a corner by having a good sense of your weaknesses. When preparing your argument, you might be tempted to linger on the bits and pieces that work particularly well. But you should spend just as much time preparing and padding your weakest points – instead of simply hoping that they won’t come up.

If preparation fails, and your argument is tanking, there are still some last-minute rescue strategies you can use.

There’s a popular saying that goes, “When you’re in a hole, stop digging.” And this definitely applies to persuasion. If you find yourself backed into an argumentative corner, don’t keep arguing as you did before. You need to cover your losses.

The first thing you can do is create a diversion. People usually don’t like to be interrupted. But if you interrupt them with questions, you can stop their momentum and steer the conversation in a different direction, while keeping the focus on them.

Strategy number two is deconstruction. When someone is trying to lay the founding blocks for a devastating argument, try to challenge each tiny assumption they make. Questions like “How do you know that?” and “How can you be sure of this?” will slow down your opponent tremendously.

Our third strategy stems from another old saying: “There’s no point in flogging a dead horse – but then it can’t hurt either.” If you have a fact or argument on your side that works particularly well, just double down. Actually, you can keep on doubling and doubling down until you figure out how to get out of the argument.

If all else fails, you can always play strategy number four: the victim card. That’s not particularly dignified, but there’s a reason why it works – people are naturally empathetic to victims. Former speaker of the house Paul Ryan played the victim card when President Obama attacked him during the debate around the Affordable Care Act. Obama claimed Ryan cared less about children than he did. Ryan responded with a series of questions that highlighted the unfairness of Obama’s attack. One of these was, “How do you think it makes me feel when you misrepresent my faith and my spiritual beliefs?”

To master the art of persuasion, set the right expectations and stay open.

As a district attorney, he recruited many young litigators. But before he hired anyone, he would make them prove their persuasion skills with a simple task: they had five minutes to convince him to go see their favorite movie.

Sounds easy enough, right? Still, even these young law professionals often did very poorly. The good news, though, is that they got better at persuasion over time as they practiced on real-life cases in court.

You may have all the skills you need to advocate for your beliefs with thoughtful questions. With time and practice, you can truly hone them. But there are a few things you’ll need to remember along the way.

Persuasion isn’t about winning – it’s about successful communication. And in order to succeed, you need to set the right expectations.

How many times have you seen someone’s view changed by a single conversation? Probably not very many, especially when it comes to deeper, contentious issues like gun control and abortion. That’s why it’s inadvisable to get over ambitious with your aims. If you do, you’re just setting yourself up for failure.

As the old adage goes, “You can lead a horse to water but you can’t make it drink.” Your aim when persuading shouldn’t be to force your listeners to agree with everything you say. It should be to guide them to draw their own conclusions based on the merits of your argument.

That’s what the art of persuasion is all about. Questions are a great way to gently nudge your audience in the right direction, but you’ll have to let them take the final steps of persuading themselves on their own. And you’ll need to remember that everyone listens in their own unique way – even if you’re talking in front of a big group. Always think about how you can appeal to and touch each and every member of your audience in their real lives.

There’s one final thing you need to remember as you practice: when you’re trying to persuade others, you need to be persuadable yourself. This means staying receptive to new facts and perspectives, and adjusting your beliefs when you’re confronted with contradictory evidence. After all, you can’t expect others to change their minds based on a good argument if you’re not willing to do the same.

When it comes to persuasion, it’s all about asking questions. If you know exactly what you’re trying to achieve, which facts are relevant to your argument, and who you’re talking to, the right questions can help you bypass people’s defenses and win them over. Questions give you the power to repeat key points, show a fault in an opponent’s argument, and lead people to draw conclusions of their own that confirm your beliefs.

Actionable advice:

Start with your best.

Questions are a great way to present facts without actually stating them outright. But which fact should you start with? It is recommended to start strong: weave your best fact into one of the first questions you use. Then, continue with your third-best fact, and save the second-best fact for your very last argumentative blow.