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.
Once you decide on the structure of an interview, it’s time to start researching.
I begin by thinking of all the questions I want to ask my guest. Then I research as many possible answers as I can to give me insight into how they might respond. During the interview, I use the information I gathered to guide my guest and fill in any missing pieces that I couldn’t find online.
Many interviewers skip doing research. In fact, some interviewers believe a lack of research is the best way to empathize with the audience. By not doing research, the argument goes, the interviewer can ask the questions the audience would ask if they could talk with the guest.
This isn’t just bad advice—it could ruin your reputation with your guest and audience.
I once listened to an interview with Derek Sivers. The interviewer asked Derek what he did with the money he made from the sale of CD Baby, the music sales site he created. By then, it was common knowledge in the startup world that Derek had given the money away. It was part of what made him so captivating. The interviewer had never heard about it.
Your audience doesn’t expect you to be like them. They deserve an interviewer who knows more than what they have time to learn. They need you to strive for a deeper understanding than they would reach on their own.
I also interviewed Derek two years before the aforementioned interview. I knew from my research that he sold his company for $22M and donated it, so I pushed him for an understanding of how he structured the donation. It turns out he used an estate planning tool called a charitable remainder unitrust, which gave him an income of $1M per year while the rest went into a charitable trust. Now that’s something most people don’t know about Derek. He found a way to support an organization he believed in while still collecting a million dollars per year for the rest of his life. I was able to help my listeners move past what was known into what was new with just basic preparation.
When I first started interviewing, I did all my own research. Today I have a team that helps me. They put together a research doc to get me started. I add to it myself, but that doc alone does a solid job of prepping me for the interview.
I had never been more thankful for that document than the morning my baby had a diaper explosion. The cleanup took longer than I expected, so I had to rush to the office after. I ended up at my desk seven minutes before my interview started. I didn’t have time to research my guest. I didn’t know a thing about him. I didn’t even know his name. But I wasn’t worried. All I had to do was open the research doc, and I was ready. At the end of the interview, my guest asked, “How do you know so much about me?”
Every research doc is broken up into five different sections:
Data: The top of the research doc has links to data—basic facts, not stories. We’re living in a world full of data aggregators, and every interviewer should know the tools that relate to their business. Here are some of my favorites:
Semrush tells me which websites send people to my guest’s website. It helps me understand a company’s marketing.
LinkedIn tells me how many people work at a company.
AngelList and Crunchbase tell me who invested in the companies I feature.
The Internet Archive shows me what a website looked like over the years.
Below the data is a timeline of the guest’s past experience. Since I’m covering the business side of a guest’s life, I like to know where they worked and for how long.
Basic Concepts: I also love having basic concepts condensed into a single sentence. If I’m interviewing a founder about her company, I want a sentence summing up the problem the company solves. If the interview is about a product, I want a sentence describing what it does. If it’s about a book, I need a sentence about its purpose. The brevity helps me explain my guest’s work to my audience.
The Hook: The research doc also includes a single sentence hook for the interview. Founders who built a $1M business are everywhere. “How a founder went from homelessness to creating a $1M business” is a story that will get the audience’s attention.
Pre-interview Notes: Then comes the most important part: the pre-interview notes. These include summaries of the pivotal stories in a guest’s life or the steps they will teach. We already covered the pre-interview notes earlier.
Additional Research: The final touch includes excerpts from articles about my guest. If a reporter, blogger, or social media influencer writes something about my guest that might help me, my team adds an excerpt of it to the doc.
You can use outsourcing companies to pull most of this information together. If you provide a clear list of questions, services like FancyHands* can put together a decent research doc for about $25. They won’t do a formal pre-interview, but they’ll do online research to find as many answers to your pre-interview questions as they can. Those services are useful in a pinch, but I prefer to do the research myself or have a team member do it.
Over time we’ve learned to look for nuances that someone new to interviewing might miss, like inconsistencies in a guest’s story. In 2012, I almost interviewed a founder who was building his reputation by implying he was a co-founder of Evite, the online invitation tool. Articles written about Evite in its early days didn’t include his name. By discovering that inconsistency, I avoided publishing a misleading interview.
Don’t stop researching when your doc is done. My favorite way to research guests is to make phone calls. I have a bad habit of waiting till the last minute to do that, but it’s still helpful. In the 30 to 60 minutes before an interview, I text and call people who know my guest—customers, competitors, friends, employees, past interviewees, anyone who comes to mind.
A few minutes before my interview with Rasty Turek, founder of Pex, the video and music database company, I texted a music industry entrepreneur I met in Los Angeles about a decade before.
I promised I wouldn’t reveal my source’s name, so he gave me as much inside information as he could. He told me that Pex is amazing, but not for the reason its founder was likely to say. He said the founder would probably highlight how the company helps music copyright owners understand how often their music is played online. Sure enough, that’s how the company described itself on its homepage.
But the remarkable thing, my source confided in me, was that it helps copyright owners claim their work on YouTube, Instagram, and other platforms. It’s controversial because some influencers become livid when their work is flagged or blocked for accidental copyright violations. Still, my source explained, the original creators need a way to claim copyright ownership of their work, and Pex helps them do that. In four minutes, I got more insight than in an hour of online research.
I also asked my source what questions he’d want answered by Rasty. This helped me make the interview useful for a target audience member. It also gave me questions I never would have thought to ask, like how did Pex get away with copying everything on YouTube into its database without getting shut down by YouTube’s lawyers?
It can feel uncomfortable calling on your guests’ contacts for help. For example, when I called venture capitalist Mark Suster to ask about a founder he knew well and whom I was about to interview, Mark was in the middle of checking into a hotel. It felt incredibly rude to interrupt him. But Mark knew my guest could be hard to get to know based on internet research, so he shared a few personal stories that revealed his personality.
What I realized is that most people want to help interviewers like me. Over the years, every person I’ve contacted has been impressed that I’d spend the time learning about my guest, even if they preferred not to tell me anything.
Guests respect that kind of research too. When Sam Parr, founder of the media company the Hustle, found out I talked to someone who worked for him, he was impressed and asked, “Do you do this to everyone you interview?” Truthfully, I don’t. Every guest is different. But I try to go above and beyond the standard research doc as often as I can.
You don’t need to have a producer or pre-interviewer to be prepared. Start by making a list of the questions you most want to ask. Answer as many of them as you can before the interview. If you come across an answer your audience should know, include the question in your research doc anyway. When you get stumped or want more depth, add the question to your outline.
The time you spend preparing will keep your interview unique and valuable. It’ll also help you feel more curious and excited about talking with your guest.
🎤 With Derek Sivers: “How A Musician Built A $22 Million Dollar Business From His Home.”
🎤 With Rasty Turek: “Investors hated Pex until this…”
🎬 With Sam Parr: “How to go from 0 to 75K subscribers in 6 months.”
Beyond the research that I do to find content for the interview, I also like to do a bit of homework to improve my relationship with the guest.
Attention to detail comes in handy in situations like the pre-interview I did with Gregory Galant, founder of the Shorty Awards (a coveted award for social media stars) and Muck Rack (a tool for helping companies in media.)