Holloway Editione1.1.1
Updated September 14, 2022You’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.
I don’t like to focus on the news because its relevance expires fast. When Jon Stewart hosted The Daily Show, he was the comic that millions of people turned to when they wanted to understand world events. After he was off the air, his episodes were removed from The Daily Show’s website.
Meanwhile, video platforms are outbidding each other for the rights to play reruns of timeless shows like Seinfeld.
I prefer to record interviews that will be as useful decades from now as they are the day I publish them. Still, news-based interviews have their place. When controversy strikes, interviews with the person at the center of the storm will draw a large audience. For me, it’s also a chance to better understand how entrepreneurs think.
Unlike the Hero’s Journey and how-to structures, news-based interviews don’t follow a clear structure, but they do have common elements. Most interviewers will launch right into the issue that made the news. That’s why everyone’s there, right? To hold off would be like forcing a thirsty man to listen to a sales pitch before handing him a glass of water.
You can see an ideal example in Oprah Winfrey’s interview (transcript) with cyclist Lance Armstrong after news broke about his doping scandal. By then, Armstrong had been stripped of his seven Tour de France titles, lost several sponsors—including Nike and Oakley—and stepped down from his Livestrong Foundation.
When he sat down with Oprah, she spent a few seconds explaining there were no ground rules, then got right to the news:
Oprah Winfrey: Did you ever take banned substances to enhance your cycling performance?
Lance Armstrong: Yes.
Winfrey: Was one of those banned substances EPO?
Armstrong: Yes.
Winfrey: Did you ever blood dope or use blood transfusions to enhance your cycling performance?
Armstrong: Yes.
Winfrey: Did you ever use any other banned substances such as testosterone, cortisone, or Human Growth Hormone?
Armstrong: Yes.
Winfrey: In all seven of your Tour de France victories, did you ever take banned substances or blood dope?
Armstrong: Yes.
The longer you take to get to the news, the more people wonder if you ever will. The interviewee is also anxious to get to the news and will have a hard time focusing on anything else. So get to it.
When news broke that Stack Exchange, the question and answer platform, was ceasing to allow sites to use its software, I got its founder to do an interview with me. My first question for him: “Joel, you have a bit of news. What’s going on?” Many in my audience were going to have parts of their sites shut down because of this decision. They didn’t have the patience for me to go through friendly banter.
Once the big news topic is introduced, there are two ways to proceed. The first is to keep pounding away at the news. A classic example of this approach is the 2010 All Things D interview that journalists Kara Swisher and Walt Mossberg did with Facebook founder, Mark Zuckerberg. News had recently come out that Facebook was sharing more personal data than people realized by using a feature called Instant Personalization. In his very first sentence, Mossberg says, “We do have some controversy we have to get through,” and starts hitting Zuckerberg with questions about why Facebook makes it so hard for people to protect their privacy.
After 14 minutes of repeated questioning on privacy, Zuckerberg was sweating so much that Swisher suggested he take off his hoodie. They proceeded with another seven minutes of questions on privacy. Then Mossberg announced, “This is my last question on this, seriously.” The live audience, exhausted from the barrage of tough questions, clapped when they heard that. Mossberg then addressed the crowd, saying, “I’m sorry if you don’t think this is important, but I do.” When he finished the privacy questions, he didn’t lighten up. Instead, he and Swisher switched to other heavy topics, including questions on whether the company had too much power and whether Zuckerberg would continue to lead the company he founded.
Interviews that focus on challenging news from beginning to end are tough to sustain. Guests get uncomfortable and even pugnacious. Audiences feel drained from what feels like non-stop combat. And the interviewer has to endure a verbal battle with someone who’s better armed. As Richard Nixon said about his career to David Frost in the most-watched interview of all time, “I know this better than you do. And I should know better because I was there.”
The alternative to endless combat is to start with the hard news, then ease off a bit. Give the guest and audience a chance to breathe. A great example of this is the Axios interview with Brian Chesky, the founder of Airbnb. After questioning the company’s big decision to go public during the COVID-19 pandemic, Dan Primack asked where Chesky looked forward to vacationing when the pandemic’s threat was over. It de-stressed the conversation and gave listeners a chance to get to know Chesky. His answer? He wanted to go to a national park so he could reconnect with the outdoors after the 2020 lockdowns.
I prefer to use the news as a springboard for more evergreen topics that will outlast the news cycle. You can see this approach in my 2009 interview with Alexis Ohanian, co-founder of Reddit. At the time, many experts in the startup community thought Reddit was a copycat of Digg, a more established news aggregator.
My first question: “True or false? You guys saw that Digg was doing well and said, ‘Let’s jump on that bandwagon.’” I could have spent the hour hitting Alexis with every accusation I read. The live audience watching us online would have been gripped, but that interview would be irrelevant today. Just two years after that conversation, Digg shut down and pivoted, having failed to keep up with Reddit.
Instead of arguing about whether Alexis copied another site, I tried to understand his thought process behind building Reddit in the first place. New entrepreneurs who discover the interview today will still benefit from learning how Alexis decided which business ideas to ditch in favor of focusing on Reddit. One of my favorite parts of the interview was how he talked about Subreddits. Back then, these communities were seen as a failed feature. Even Alexis didn’t seem enthusiastic about them. But when he explained how he wanted Reddit to be led and grown by community leaders, he displayed timeless business logic.
So here’s my advice to you: conduct news-based interviews because they’ll deliver an audience. The top ten most-watched interviews in American history have all been with newsmakers at the center of controversies. But if you want those interviews to have lasting relevance, transition them to topics that endure.
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🎬 With Joel Spolsky: “Breaking News: Why Didn’t Stack Exchange Work?.”
🎬 With Alexis Ohanian: “No, Reddit Didn’t Copy Digg. Here’s How It Was Built.”
This interview format was popularized by Joe Rogan, the comedian-turned-podcaster who signed a $100M deal to make his show exclusive to Spotify listeners. Rogan can talk to his guests for more than three hours per interview, often with a whiskey in his hand. His conversations bounce between topics like discipline, nutrition, drugs, and exercise, without much more connecting them than Rogan’s interest.
These types of interviews seem to lack structure, but when I studied Rogan’s transcripts, I saw a clear methodology. I call these interviews “serendipitous” because the host moves quickly through topics, looking for surprise gems. They’re like a pub crawler who goes from bar to bar, spending more time in the ones that are fun and moving on the moment things get stale.
A good example is Rogan’s interview with Elon Musk, the billionaire behind SpaceX and Tesla. Listen to how fast they zip through topics. They take just seven seconds to greet each other. Then Rogan asks about flamethrowers. Musk gives answers I’ve heard him give before, so three minutes and 45 seconds later, Rogan ditches the topic.