Avoid Interviewers’ Worst Questions

4 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.

Many folks that offer interview advice to new podcasters include lists of questions to ask guests. These lists are often packed with what I call “most” questions:

  • What book had the most influence on you?

  • What’s the worst thing that happened to you?

  • Who was the most helpful person in your life?

I see what the writers are going for. They know that interviewers have a limited time with guests, and they want to maximize that time by focusing on the biggest, best, and most significant aspects of guests’ lives.

The problem with this approach is that it freezes people. It forces them to do too much mental work for too little payoff.

Take that last question, “Who was the most influential person in your life?” Your guest has to first define what “influential” means to her. Then she has to make a mental list of people who influenced her. Then she has to identify the person who was most influential. Then, after she comes up with an answer, she might wonder if she might insult someone she didn’t pick. Would Mom feel bad, for example, if she picked Dad?

Meanwhile, as an interviewer, you probably don’t need the person at the top of their list. You’re just trying to understand one of their influences. So why not simply ask, “Could you tell me about someone who had a big influence on your life?”

Not only will your guest be able to answer the question more quickly, but there’s a good chance this softer approach will lead to the most influential person anyway. Without the pressure on your guest to name the single most important person in their life, they will feel freer to talk to you.

Well-meaning people make this mistake in daily life all the time. When I finished backpacking around Europe, I got off the plane and went straight to my friend’s home for dinner. Their first question was one that I was asked by others for weeks after I returned: what was your favorite city?

I wasn’t sure. Was it Pamplona, where I ran with the bulls? Paris, where I sat in outdoor cafes and quietly journaled for days? Or one of the dozens of other cities? So I said, “It was all amazing.”

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Was I overthinking it? Of course.

I eventually realized they just wanted to hear about my trip, so I’d say, “I’m not sure which is my favorite, but one of them was …” and tell a story from my trip.

As an interviewer, I don’t want to count on people making that leap. So I usually rephrase all “most” questions in a way that gives guests options. Instead of asking “Who’s the most important person you hired?” I go with “Who’s an important person you hired?”

There are exceptions to this rule. For example, when I ask a founder what their top source for customers is, I don’t want to hear about the third most effective channel. I’m trying to understand what’s working best. It’s a factual piece of information that founders should know the answer to, so that’s what I ask for.

We’re taught to seek out click-baity answers to complex questions. In reality, the lives of our guests are much more nuanced. Don’t put them on the spot by asking “most” questions. Give them the opportunity to explore your question and answer it with the depth it deserves.

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