Holloway Editione1.1.1Updated September 14, 2022
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.
The most-watched interviews in mainstream press have always been news-based. In 1993, when Michael Jackson was accused of child sexual abuse, he sat for an interview with Oprah Winfrey. It became the most-watched interview in American history, with 90M people tuning in. The Top 10 list of most-watched interviews is full of politicians, royalty, and accused criminals who made headlines around the world.
But you don’t need to land worldwide headliners to take advantage of breaking news. All you need are people making headlines in your audience’s world. My world is the tech startup community. One day, two well-known people in my world became newsmakers.
I read somewhere that Matt Mullenweg was upset. As the founder of WordPress, the world’s most popular web-publishing platform, startup founders paid attention to what he said. Matt was frustrated that Chris Pearson, a popular designer and software engineer, had the audacity to sell a WordPress template instead of making it free like the WordPress platform itself.
Bloggers in the WordPress community were writing about the fight. So were large tech news sites. Meanwhile, people on both sides of the argument were tweeting their opinions. It was big news in the startup world. So I asked both Chris and Matt if they’d let me interview them together via Skype to understand each of their points of view. They agreed.
After I published it, hundreds of sites linked to the interview. For years afterward, people in the WordPress community made sure to tell me what they thought of the debate and whose side they were on. That’s the power of news-based interviews.
The way to land newsmaker guests is to pay attention to the news in your world and quickly send invitations to the people at the center of the stories. At first, it seems hard to get people who are in the news to agree to an interview. The world is talking about them. They must be too busy. But what I’ve found is that these busy news cycles are just another motivated moment. The people in the news are often as eager to clarify their stories as listeners are to hear them.
The key is to jump on the news as fast as possible. If the person you’re after says they’re busy and asks to do it a few days later, tell them that in two days they won’t reach as many people. Let them know that people make up their minds fast and change them reluctantly. If they don’t give their side of the story, the world will have solidified their opinion of them without their input. They need to capitalize on the story while it’s hot if they want to reach as many people as possible.
caution A word of caution: don’t destroy relationships by being desperate for a story. You want to maintain good, long-term relationships with your guests, so don’t pressure people to do interviews that aren’t in their best interest.
When I first asked Gagan Biyani for an interview, he turned me down. He was the founder of Sprig, a food delivery startup that raised over $50M in funding before shutting down. I kept checking in with him, and he kept insisting he wasn’t ready to talk about it. Three years after the shutdown, he agreed to let me be the first person to publish an interview about the story. Be patient.
But if there’s a chance to land a newsmaker, don’t waste time. And don’t assume that if your reach is too small, newsmakers won’t want to be interviewed by you. I used to think that way, then I turned my disadvantage into an asset. I started telling people at the center of controversies that my smaller audience would mitigate their risk. If they flubbed their story on CNN, the world would know. If they did it on my podcast back when it was unknown, the impact would be much smaller. This is one case where a smaller audience can help you.
Another thing to help you land newsmakers is your mission—your higher purpose. In a world full of “gotcha journalism,” practice “I get you journalism” instead.
People in the public eye are surrounded by “gotcha journalists” who try to make a name for themselves by extracting scandalous revelations. That’s not my goal or the aim of this book. We want to say to our guests, “I get you. I understand who you are and want to learn more.” Most high-profile guests appreciate that. It can be disconcerting to have their lives dissected and evaluated by people who’ve never met them. They want an honest chance to give their perspective.
The trickier part of landing these guests is getting through to them, although it’s easier than it used to be. Social media platforms like Twitter and Instagram make it simple to send private, direct messages. Whois domain searches help me find phone numbers of website owners. Sales prospecting tools like Hunter.io* and RocketReach* allow me to find practically anyone’s email address.
If you’re tech-savvy, you’ll find new opportunities for connections constantly. For example, I discovered that if the person I want to reach has an iPhone, I can easily reach them by text. All I need is their email address, which is easy to find. If I pop that into Apple’s Messages app and send a text, it’ll show up on the recipient’s screen instantly. Using FaceTime, I can use their email to make an audio-only call that comes across like any other phone call.
As clever as all those methods are, my favorite way to reach guests is to ask for a referral. Everyone I interview becomes another helpful connection in my personal network. The interview booking software I use, Acuity Scheduling,* automatically adds all their contact information to my phone’s address, so I have multiple ways to reach them. If I need to reach a newsmaker or anyone else in a hurry, I can text or call past guests and ask for introductions.
🎤 With Gagan Biyani: “How Sprig lost over $50 million.”
🎤 With Bari Baumgardner: “How this live events company pivoted in a time of COVID.”
It can be hard to persuade guests to do interviews. So I call on stories of their heroes to help me like I did the time I wanted to interview a writer who was at the center of a scandal.
I used to check TechCrunch the first thing after waking up. I wanted to see what was new in the startup world that I loved. One Friday morning, I woke up and read that a TechCrunch writer, Daniel Brusilovsky, “allegedly asked for a Macbook Air in exchange for a post about a startup.”