Draw Out Interesting Stories

7 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.

A lot of advice can sound cliché. But when you share advice through stories, it becomes memorable and actionable.

When I interviewed Brad Feld, an entrepreneur turned investor, he told me that business is a series of successes and failures. That’s a fact, but it seems so obvious that it doesn’t have much impact on an audience.

I needed a story. So I followed up with, “Can you give an example of that?”

Brad said he invested in the startup BeMANY. After a strong effort to grow it, the founder, George Jankovic, “got to the point where the business simply wasn’t working.”

As the biggest investor in the business, Brad said to him, “Is it worth a year of your life to keep working on this business just to get back to a place where, maybe, if you reinvent yourself, it’ll be successful? Or is that opportunity cost—a year of your life—worthwhile?”

Brad then told Jankovic to turn off his phone, take his new wife to dinner, and just give himself time to think. When he got back to Brad, he decided to close the business.

After that, Jankovic raised money to buy NutriSystem, the diet company that hit on hard times. By improving its marketing and operations, he turned the company into a $2.5B business. If he hadn’t accepted failure at BeMANY, he might not have reached that level of success.

I’d bet that long after you finish reading this book, that story will stay with you.

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I recorded Brad’s interview with a live audience watching me online. As soon as we finished, Christoph, the founder of an outsourcing company I worked with, called me. He said, “Andrew, I’ve been struggling with this company for a long time, and it’s not working. I think it’s time for me to leave Central America, go home to Europe, and start over.”

We lost touch after that call, but a few years later, he found himself in San Francisco. I invited him to my house for Scotch. As we sat down, he told me his new company was doing well financially, and now he’s leading a chapter of EO, a group of entrepreneurs whose businesses do over $1M per year.

Christoph told me that people said he should close down his last company, but hearing my interview with Brad convinced him.

That’s the power of a good story.

So how do we get people to share their stories? I used to try asking, “Could you tell me a story?” Smart people often dismissed that request. Stories sound like what you tell two-year-olds, not how you talk to a smart audience. Those that didn’t dismiss the need for stories often froze because coming up with a story is too much pressure.

I learned to rephrase my request. Instead of “could you tell me a story about that?” I used phrases like the following:

  • “Tell me about a time when you did that.”

  • “Do you have an example of that?”

  • “Tell me about the day you signed the agreement to sell your company.”

  • “Take me to the moment you quit. What did you say?”

Notice that I don’t ask, “Tell me about the most important time …” Asking people “most” questions like this distracts them from the conversation, as you’ll see in the next section.

Take the pressure off your guest by asking for one story. Any story. It doesn’t have to be the pinnacle of their life, but more often than not, the story they remember and share with you is one of their best. If your guest can’t think of an example, share one of your own. It allows you to model what you want them to do.

That’s what I did with Allie Magyar, founder of the events platform HUBB. I wanted to understand how one of her childhood difficulties shaped her. She knew she had some but couldn’t think of any. So I told her about the time when my brother fell when we were kids. With onlookers watching, my father whispered to my brother, “We don’t have health insurance.” My dad said that since we couldn’t go to a doctor, he’d need to recover on his own. I told Allie that seeing how finances could compromise health pushed me to earn enough money as an adult to never let it be an impediment in my life.

That triggered something in Allie. She told me about the time in her childhood when her dynamic, successful dad had a drug and alcohol problem. The family finances suffered. Still, she wanted a popsicle, so her mom gave her the last dollar they had. It was a windy day when she accidentally dropped the dollar, and it got swept away. Her mom was reduced to tears. Money was scarce. So they chased the dollar down till Allie got it back.

She went on to explain that that’s how she runs her company now. She said, “I still manage a budget like my dollar is flying down the hallway.”

Compare that poignant popsicle story with the answers most business people want to give. They’ll share flat statements like “I like to manage my company’s money well.” It isn’t nearly as memorable or impactful as a good story.

Seek out specific and interesting stories in your interviews. Pay attention when your interviewees make general statements about their lives, and follow them up with a request for specific examples.

If they say, “I like to celebrate my wins and failures,” you can say, “Tell me about a time you celebrated a failure.”

If they say, “Remembering my past successes helps me get past my current challenges,” you can ask, “What’s a past success that you think about often?”

If they tell you, “I still turn to my mom for help,” you can ask, “What’s a problem you turned to your mom for help with as an adult?”

Key insights do nothing for your audience if no one remembers them. Use stories to make them stick.

Listen: “A Time When You …”

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