Asking Tough Questions

You’re reading an excerpt of Stop Asking Questions, by Andrew Warner, a veteran podcast host of 2000+ episodes. The book explains how to lead high-impact interviews and learn anything from anyone. Master the craft of interviewing with this complete digital package. Purchase now for lifetime access to the book and extensive audio and video resources.

I grew up in New York City, so I prefer to be blunt and ask for what I want. But as an interviewer, if I don’t take some of the sting out of my questions, my guest could become defensive, stop paying attention, and maybe even walk off.

A good example of this comes from a BBC interview with conservative commentator Ben Shapiro. The video went viral because he stormed out before it was over. I had the interview transcribed so I could study it and understand what the interviewer said to elicit that response.

Right from the start, the interviewer asked tough questions. “Haven’t the conservatives run out of ideas in America?” he asked. Then he hit Shapiro with an observation that new ideas were really coming from the Left, instead of Shapiro’s conservatives. Then he got under his skin by asking, “Why is it that a bill banning abortions after a woman has been pregnant for six weeks, is not a return to the Dark Ages?”

These are all legitimate questions for a conservative thinker, but reading how question after question unfolded, I understood why the barrage might make Shapiro feel personally attacked.

In response, Shapiro accused the interviewer of bias. “Why can’t you just say you’re on the left?” And he argued against almost every question he was asked. “Would you ask the same question to a pro-choice advocate?” And eventually, he walked off.

In reality, the interviewer, Andrew Neil, chaired an organization that owned The Spectator, a right-wing magazine. So their politics weren’t in opposition, but the tone of the questions felt combative.

If dramatic frustration like this is what you want from your guest, by all means, be blunt. Don’t take a moment to soften your questions. But that’s not what this book is about. My goal is to find ways to understand my guests and learn from them, not create an explosive media moment.

A more productive way to ask tough questions is to put the words in someone else’s mouth. I learned this technique from watching Mike Wallace, who was considered one of the toughest interviewers of the twentieth century. The most cited example of his chutzpah is when he asked Iran’s leader, Ayatollah Khomeini, if he was crazy.

I hunted that interview down to see how he did it so I could have a model for asking challenging questions.* Here’s what Wallace said:

“Imam, President Sadat of Egypt, a devoutly religious man, a Muslim, says that what you are doing now is—quote—‘a disgrace to Islam.’ And he calls you, Imam—forgive me, his words, not mine—‘a lunatic.’”

Turns out Wallace didn’t call Khomeini a lunatic. He cited someone else calling him that. There was a moment of friction until the translator explained that Wallace was quoting Sadat. Once that was cleared up, the conversation continued. A few minutes later, Khomeini agreed to release some of the American hostages he was holding at the time.

If I have a series of tough questions to ask my guest, I look online for examples of other people asking them. For example, I wanted to ask Ryan Hoover of the maker community Product Hunt why he didn’t have enough women in his community. I did some research and found members of his own community bringing up the issue. Instead of taking a combative response, it allowed him to tell me about the partnerships he was working on to recruit a more diverse membership.

What if I can’t find someone else taking the position I want to bring up? That’s when I create a theoretical person. For example, when I talked with James Altucher about his self-help book, Choose Yourself, where he said we should be happy with who we are, something occurred to me. He’s probably happy now because he’s rich, not because of the techniques in his book.

I asked, “What do you say to someone listening to us thinking, ‘James is only happy now because he has money in the bank. If he didn’t have it, he would be right back to wrestling with his own inner demons like everyone else?’”

James acknowledged that he’s happier because he’s wealthy, but he talked about how he still has inner demons to deal with and uses what he wrote about to deal with them. And he said he used what’s in his book when he was at rock-bottom financially and needed to climb out.

Here are a few other examples of how I phrase criticism through other people’s words:

• What do you say to someone who’s listening to us and thinking …?

• What would you say to someone who thought …?

• I imagine someone listening to us thinking … What would you say to that?

By putting the words in someone else’s mouth, you eliminate the “me versus you” feeling that comes with asking tough questions. It turns the interviewer into a partner who’s working with the guest to understand. And that’s where you always want to be.

But some questions are so shocking they require their own strategy. That’s next.