Don’t Sound Needy

6 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.

Most people think an interviewer’s job is to ask questions. I can tell you from experience that it’s not.

I learned this at a hilltop house in Los Angeles overlooking the ocean. While my friend Steve and I had a beer by his pool, I asked him what he did to earn such a gorgeous place.

“We’ve known each other a long time because our wives are friends,” I said. “But I never asked you about your business. What do you do, Steve?”

He said he made apps. I saw a quick smile come across his face, so I followed up with, “How’d you get started?”

That made him beam. He told me how he started creating apps for BlackBerry. He did it before Apple announced the iPhone, before the word “app” was known by the average person, and before the hottest hotshots in Silicon Valley had apps on their product roadmaps.

I was fascinated, so I asked him more questions. How did he know apps would be big? How did he make the transition to iPhone apps? How did he get his first customers?

As we chatted more about his company, his enthusiasm and pride grew. But when I got up to get another beer, he asked me to grab him one. Then he asked me if I needed help getting started in business. That’s when I noticed the tone of our conversation was changing. We had started out as peers, but my incessant line of questioning made me sound like a student. Or worse, a needy intern. And he was treating me that way.

The same problem started creeping into my interviews. After a few questions in a row, I started to sound clueless.

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“How did you get started?”

“How did you grow your company?”

“How could I do that?”

All curious people will encounter this problem. Asking questions makes you seem needy. And if you’re needy, people don’t respect you, which reduces the quality of their answers.

A couple of years into my interviewing career, I started to get a chip on my shoulder about being minimized by guests. I’m ashamed of some of the ways I reacted to it. My worst moment was waiting for Rod Drury, the founder of accounting software Xero. He was late, and I had a live audience watching me wait. I was embarrassed and aggrieved. So I started mocking him on camera for not caring. When he did show up a few minutes late and was incredibly nice, I felt like a jerk. I still feel guilty every time I see a Xero ad or hear a friend talk about how amazing his software is.

One of the ways I responded to that period of frustration was by taking charge of the conversation from the start. If the guest was in a loud room, I told them to move. I didn’t ask. I said, “You need to find a quiet place to record, or the audience won’t be able to hear your story.” If they didn’t have a strong internet connection, I told them to find a way to fix it, or we’d need to reschedule for a day when it would be better.

Guests appreciated that kind of leadership, so I brought the attitude into my interview. I rephrased my questions as directives. Instead of asking, “How did you get your first customer?” I said, “Tell me how you got your first customer.”

At times it felt rude. Was I being bossy instead of kind? Did they think I was too demanding? Too pushy?

Not at all. In fact, switching about half my questions to statements changed how people saw me. They stopped treating me like a needy kid and saw me as a leader who would guide them through their interview. I no longer felt ashamed or resentful of perceived slights. It felt good to guide them toward telling the best possible stories.

Interviewees appreciated this direct approach. Being interviewed requires a lot of trust. Guests want a host who will keep them sounding interesting, helpful, and bring out stories they’d never think of on their own. That kind of guidance doesn’t come from a needy intern. It comes from a leader. Real leaders use clear statements and make thoughtful requests.

If you were going hiking with a guide, you wouldn’t want her to keep asking, “Do you want to go left or right?” She’s the one with experience. It’s her job to know what’s down each path and to understand your interests well enough to pick for you. That’s what your interviewees need from you. Guide them.

So stop asking questions. Start leading your guests through better conversations.

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