Home Run 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.

End on a High Note

One day, as I was leaving my office, I got a call from a prominent Silicon Valley founder I interviewed earlier that morning.

“I’m upset with you,” she came right out and said.

I was stunned. I racked my brain trying to figure out why she’d be mad. Her interview went off without a hitch. If anything, I felt like I was more accommodating than usual. She was in a relationship with someone famous. To preserve her privacy, I didn’t bring it up, even though it could have given my show a traffic boost. We focused strictly on her business, and I even let her promote more than I normally would.

My only tough question came at the end. We had scheduled the interview multiple times, and she didn’t show up. She seemed to have done that to another interviewer, who mentioned it on his podcast. So I asked why she didn’t show up when she said she would.

She apologized and explained how overbooked she was lately—totally understandable for a founder of her stature. I thanked her, closed out the interview, and thought nothing of it.

Apparently, she thought of nothing but that last question.

I asked one tough question. Just one. And I waited until we had built enough rapport for me to bring it up. Why did that make her upset? She was both a listener of mine and a paying customer. She knew I liked to have deeper, more meaningful conversations than most interviewers were willing to risk. This question was a softball by my standards.

Why?

My interview coach read the transcript from our interview and quickly identified the problem: I violated the peak-end rule.

The peak-end rule is a cognitive bias that affects the way we recall events. Humans tend to remember two aspects of an experience more than anything else: the peak (i.e., most intense) and the end.

By saving my toughest question for last, I unwittingly stacked the peak and the end into one dramatic moment. It was the only thing my guest remembered from our talk. No wonder she was upset.

Up until that moment, I always saved my toughest questions for the end. I wanted to close out the interview with something memorable for my audience. I thought my interviewee would trust me enough to know my intentions were good. After receiving that call from my upset guest, I realized she probably wasn’t the only one. Other guests might have been hurt by my actions too—they just didn’t tell me.

But it wasn’t just the peak-end rule that was working against me. Saving the hardest questions for last invoked an even more primal emotion: vulnerability.

I once listened to Oprah Winfrey being interviewed at Stanford University, where she shared some behind-the-scenes details of her famous talk show. She said that throughout her storied career, each of her guests would ask the same question after the interview: “Was that OK?”

Barack Obama and George Bush both asked the question. Beyoncé, who taught Winfrey how to twerk on live TV, also asked. Even the most seasoned public figures feel vulnerable after a performance. Asking a tough question at the end was like a punch to their confidence before saying goodbye.

I decided to stop saving my gutsiest questions for last. I would ask those somewhere in the middle and then end the conversation with something easy.

My goal was to give my guests a home run question they could knock out of the park and leave the interview feeling confident about their performance.

But I didn’t stop there. I started anticipating my guests’ need for validation. When an interview ended, I thanked them, told them they did well, and mentioned one specific thing I liked from our conversation.

Before I made this adjustment, guests would routinely ask me to give them another chance to record their interviews. “I think I could have done better,” they’d say. “How about we record again next week?”

I saw a drastic reduction in these requests by ending interviews on a home run question. Guests started feeling happy and confident after our interviews instead of vulnerable and regretful.

As an interviewer, it takes nothing to end your conversations on a high note. But for your guests, it means everything.