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.
Billionaires turned to finance legend Alan “Ace” Greenberg for advice. He ran the Wall Street firm Bear Stearns at its prime. I was an unpaid college intern and wanted to learn from his experience. So I asked for a meeting and hoped he’d agree to the type of connection that could change my life. He said he wanted to help ambitious employees like me, so he set aside time for us to talk.
I walked in to see him, holding a notebook full of research I did based on obscure articles and conversations with people who followed his career. He sat at the end of a giant table he shared with dozens of his employees, most of whom seemed to be talking on two phones at once. It was loud, but his eyes and attention were only on me, eager to help. That’s when it hit me. I didn’t know how to access any of his wisdom.
I asked him about his start. He told me how he sat next to the firm’s chairman and slowly took on more of the man’s work until he was the firm’s leader. I had already read that in an old Forbes article. So I asked what makes someone successful. He told me that instead of an MBA, he likes people with a PSD, which stood for “poor, smart, and a desire to be rich.” I had read that in an old BusinessWeek article.
He was warm and attentive, but I couldn’t figure out how to go deeper and learn anything new. Finally, he stood up and ended our mutual discomfort. Shaking my hand to indicate it was time for me to leave, he said, “A fella once told me, ‘If you’re doing what you enjoy, you never have to work a day in your life.’ I hope that quote helps you.”
I knew I’d missed a golden opportunity, but I wasn’t sure what I’d done wrong. It was my one shot to tap into Ace Greenberg’s wisdom, and all I got were facts I’d read before and some canned advice I could have found on my college bulletin board.
Today, we all have a world of opportunities to have conversations with people who could change our lives. Anyone with a computer or phone can record an interview, learn from people they admire, and share it with the world. Interview podcasts democratized access to these conversations. YouTube allows anyone with a camera to distribute their video interviews instantly. Blogging offers a place for text-based interviews. I’ve even seen one-minute interviews on TikTok gain hundreds of thousands of views. New online platforms are popping up constantly.
Offline opportunities are growing too. Conferences, meetups, and other events use interviews as an alternative to the traditional presentation.
Let’s be real, though. Most of these interviews are simply insipid content thrown together by people who don’t know how to tap into someone’s greatness. I don’t blame the interviewers. Nobody taught any of us this new craft.
Until the 1900s, publishing interviews was virtually unheard of. It was an ingredient in good journalism but hardly ever the finished product. Late-night TV talk show hosts were the ones who popularized the interview format. They needed an easy way for celebrities to shine without roping them into skits or other elaborate performances. From there, interview-based news shows became the work of serious journalists, who made their reputations by getting politicians and other newsmakers to reveal shocking information.
It was never my goal to create “gotcha” moments in interviews. I wanted to learn from people I admired—my heroes. I was desperate to improve.
Even though I graduated with a degree in finance, I didn’t end up working in a bank or investment firm. I fell in love with entrepreneurship and started an online greeting card site that did over $30M in revenue. After selling it and taking a few years off, I came back to the startup life with an online invitation site. It completely bombed. It was so bad that even my wife refused to use it when she threw me a birthday party. I blew $300K on the business, but what really hurt was that I didn’t know why I’d failed. I couldn’t move forward with my business life until I knew how I could do better next time.
I became obsessed with interviewing after that second company failed. I sought out conversations with successful founders I admired to understand how to build a better business. I wasn’t just hanging out with my guests. I was determined to use my interviews to become a better entrepreneur—a better me.
Unexpectedly, interviewing became my business. I started a podcast interviewing proven tech startup entrepreneurs like the founders of Airbnb, Dropbox, and Y Combinator. In each interview, I learned a bit more about how to run a company, including growing an audience, systemizing operations, and hiring. That grew into Mixergy, a site for ambitious entrepreneurs.
Other entrepreneurs were equally eager to learn how to build a better company. As they showed up to listen to my episodes, advertisers bought ads to reach them. My interviews got so good that fans paid to listen to them and take my master classes.
Over the course of ten years, I interviewed more than two thousand people I admired. No one ever taught me how to interview, but I seized the opportunity behind every conversation by studying the hell out of the questions I asked and the responses I got.
In the years that followed, I spent $38,188 to have my interviews transcribed. Then I hired producers and coaches to go over my conversations to help find patterns in the responses. If a technique worked, I added it to a doc so I could keep reusing it. When something didn’t work, I deconstructed it to understand how I should have done it better. The improved version went into the doc.
I realize now what was missing when I talked with Ace. I wanted to learn, and he wanted to teach, but that desire is not enough. Interviewing is more than just asking questions. It takes skill to help someone teach what we want to understand—skills I’ve spent thousands of hours learning to master. The doc I created organized the skills I’d accumulated through interviewing. I’m sharing them with you so you can improve your podcast or in-person interviews, or simply have better conversations with people you care about.
This book is organized into four parts, following the order I’ve used when teaching new interviewers over the years. I noticed people first want quick, actionable techniques. So Part I is full of conversation tips you can master quickly and use for the rest of your life, in both interviews and daily conversations.
Once I give you the quick wins, you’ll probably want to do the deeper, harder work of learning how to prepare for and structure an interview. So that’s Part II. Then, when you have your skills nailed, you’ll be eager to land your ideal interviewees. Part III focuses on how to identify good guests and convince them to sit for an interview. Finally, Part IV will give you the fundamental aspects of the business side of interviewing. If you can’t make interviewing profitable, it’ll be harder to make it sustainable.
As I mentioned, this format is based on how others I worked with preferred to learn. If you have different preferences, feel free to jump around. Just avoid limiting yourself to what you think you need. Conversations are unpredictable.
caution One final piece of advice: Don’t be rigid. You can’t force each of these techniques into a conversation. Use them as guides, but don’t be obsessed with using them perfectly. I don’t. You’re about to get to know and learn from your heroes. Enjoy it.
This Holloway Edition includes additional exclusive digital content. You will get more out of this book by hearing actual conversations with the author.
When reading online, throughout this book you will find audio clips selected to illustrate different conversational techniques.
Also included is a three-part podcasting tutorial, presented in conversation with the author, plus additional resources for that course.
Details are at the end of the book.