Help Guests Go Deeper

5 minutes

Holloway Editione1.1.1

Updated September 14, 2022
Stop Asking 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.

Have you ever met someone who seems so perfect that they feel fake? I was starting to feel that way in my interview with Taro Fukuyama. So I wanted him to tell me about something that didn’t go well.

I asked if Fond, the employee reward company he launched (previously called AnyPerk), had hit its first million dollars.

“More than that,” he shot back.

Well, how about the customers? He started listing blue chip brands that signed up with him: Virgin America, Salesforce, Cushman & Wakefield. Then he explained that they were just the tip of the iceberg.

Isn’t competition heavy? “Actually, we don’t have that many competitors right now.”

I can’t blame him for talking up his company. As the founder, his job was to promote his company’s success on my podcast. Plus, he deserved to be proud. A few years before, he was sleeping outside a Taco Bell, listening to my interviews, planning to be as successful as the entrepreneurs I talked with.

Still, the reason people listen to my interviews is to learn from my guests. They want to see how successful founders get past the kinds of obstacles they’re likely to face.

How could I get him to talk about a failure? A setback that might have a valuable lesson for my listeners?

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I ended up using a technique that’s always worked for me: I told him what I wanted and why I wanted it. I call this “share your why.”

“Tell me about a time you were depressed,” I said. “Let me see that you’re human, not just a guy who’s a beaming Tony Robbins Jr.”

“Oh.” His attitude changed. “This is my first company. I didn’t know how to run a company. I didn’t know how to manage people.” The conversation went in a new direction.

He explained that when investors pressured him to grow faster, he started “managing people by anger.” He would say, “Hey, you’ve got to do this. You have to stay until X time because I’m staying until 11 p.m. every day.”

That’s not the type of attitude the founder of an employee engagement company would usually fess up to. But every leader can relate to his pressure. And it was valuable to learn how he went about solving his problem by talking to his employees one-on-one, taking responsibility for creating a happy and productive culture.

I didn’t realize how often I used this technique until I talked with Ashwin Vishwanathan, a banker and regular Mixergy listener from Singapore. I met up with Ashwin when I recorded a few interviews in his home country. Unprompted, he said he heard me use the “share your why” technique so often that he started using it at his work. Just like I do in my interviews, I asked him for specifics. He hit me with a story that proves this technique works even outside of interviews.

He told me that when he decided to quit banking, his boss’s boss called him in for a meeting. The executive, a dour man who was always stressed, ripped into Ashwin. “What are you doing? I heard you’re quitting.”

Ashwin gave a prepared answer and was met with a forceful stare. Then Ashwin looked at the executive and said, “What’s your motivation?” That crossed a line. Too personal for a Singaporean banker. So Ashwin looked into his eyes and slowly said, “I’m asking because I’ve always wanted to be an entrepreneur. If I don’t do it now, I’m worried I might never do it. I’m not sure how to find the motivation to give that dream up.”

His boss paused, looked at him, and then started speaking with more empathy. He explained that he, too, once wanted to start a company. When he was ready to take the risk and quit his job, the bank gave him a raise. He stayed. Then he landed a promotion. Then another raise. The upward path was good, but it also locked his family into a lifestyle he couldn’t give up. Now, with kids in expensive American schools, there was no way he could leave.

The executive spent 45 minutes reminiscing about his life and decisions with Ashwin. Then he ended by telling Ashwin that if he wanted to return to banking after entrepreneurship, there would be a home for him at his company.

Share your why. Give people a heartfelt reason to help you.

Listen: Share Your Why

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