When You Must Wing It

4 minutes, 1 link

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.

Everyone has a plan until you get punched in the mouth.

Mike Tyson’s famous insight applies to interviews as much as it does to boxing.

You should go into every interview with an outline. That’s why I gave you five different interview structures to work from. But if you aren’t willing to ditch your plan, you’ll miss opportunities and cause unnecessary friction with your guests.

I’ve learned this lesson the hard way—on multiple occasions. The first time was when I interviewed Fred Wilson, an investor and Twitter board member. The week of our interview, Fred found himself at the center of a controversy between Twitter and startups building apps for its platform. Business Insider reported: “Holy Cow Did Twitter’s Top Investor Drop a Bombshell on Twitter App-Makers Today.” Fred seemed to say that Twitter was going to put those small companies out of business by stealing their best features.

But instead of bringing up this news during our interview, I rigidly stuck with my original outline. I focused on how he built his venture capital firms and made early investments in fast-growing startups like Etsy, Twitter, and Kickstarter. In hindsight, I missed a massive opportunity to report on something newsworthy and educational for my audience.

Another time I stuck with my plan too tightly was at my first live event in front of three hundred fans. I interviewed three entrepreneurial giants on stage: Gary Vaynerchuk, Tim Ferriss, and Hosea Jan “Ze” Frank. By the end of the event, all three of them were frustrated with me.

My goal was to understand how they built their businesses by creating passionate fans. When Gary handed out sweatbands featuring his wine show’s logo, I grilled him on how he came up with that cool-looking swag. He kept telling me he didn’t know how his creative process worked. He definitely didn’t use the step-by-step approach I was pushing him to articulate. Regardless, I questioned him relentlessly because we had agreed that I would dissect how he built his business. I was obtuse.

The mistakes kept piling up. Since my interviews usually lasted an hour, I kept firing off questions, even though people at a live event don’t sit still for long. Attendees started talking to the bartenders and each other, but I didn’t let up. The panel went way longer than it should have, all because I had an outline, and I refused to accept the need to set it aside.

After my live event mistake, I accepted that I had to toss my preparation aside when I sensed a better approach. That became harder when I started working with producers who pre-interviewed guests. I hated ignoring the notes my producer worked so hard on, especially since I knew my interviewee also dedicated time to the pre-interview call. But both my guests and producers were grateful when I set aside my outline because I felt there was a better conversation to be had without it.

My on-stage interview with Gary, Tim, and Ze needed a major detour from the outline, but most instances are less dramatic. The more common experience is when a guest insists on telling a story in a way that’s less interesting than an experienced storyteller would tell it. I have to accept that. It’s their story, not mine. As an interviewer, you can’t bully your guest into telling their story your way. If you must reshape their story’s structure, do it in editing (but be faithful to their intent), not in the conversation.

The outline—and every other interview tool—is in service of a good interview. If you think there’s a better conversation to be had without those tools, set them aside.

Listen: Ditch the Outline

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