Doesn't Hurt to Ask summary

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.

The author 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, the author still made a comparison between the two systems. And he set up the president on a path to discussing why that is – even though the author had his own opinion on that, too. The author had chosen the right question, at the right time.

The author 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.

You’ve just learned about the 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.

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

Instead of answering the question, the author asked his friend 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? His friend didn’t have an answer.

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.

As a district attorney, the author 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.