Interview Structure 1: Hero’s Journey

10 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.

Throughout human history, knowledge has been passed down from generation to generation. Not with charts and spreadsheets, but with stories.

Stories have a way of embedding lessons into our minds. They help us remember hard-earned wisdom we’d otherwise forget. That’s why, as an interviewer, my goal is to get guests to tell me stories from their lives—not just share what they’ve learned.

The quintessential human story is what Joseph Campbell dubbed the Hero’s Journey. But before we get into that, let me tell you a story of my own.

Shortly after starting my first company—an online greeting card business—I was struggling to make sales. Banner ads were an important part of my business model, but I didn’t have the chops to convince sponsors to take a chance on my site. That’s when I learned about Rosalind Resnick, a seasoned entrepreneur whose company sold ads for online businesses. I thought, if I could just get Rosalind to help me, my business might survive.

So I called her office. Then I called again. And again. But every time I called, I was turned down because my company was too small. I offered to split my revenue with them 50/50. No dice. I tried everything to persuade them to work with me. Finally, one of the sales reps politely asked me to stop calling.

But I was desperate. My company was on the verge of folding, and I needed ad revenue yesterday. So I tried something different. Instead of calling, I showed up to Rosalind’s office unannounced. I found Rosalind and handed her a check for $2,000, which was all the money I had left in my bank account. I said, “I know you think we’re too small, but I guarantee that if we work together, we’ll both make money.”

Rosalind was surprised, to say the least. But I continued. “Take this check, and if you ever doubt I’m worth working with, you can cash it and make an easy $2,000.”

At that point, Rosalind told her team to start working with my company immediately. We went on to make millions of dollars together, and she gave me back that check, uncashed.

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Where did I learn to make such a bold move? I struggled to recall. It certainly didn’t come from any business class. But then I remembered a biography I read as a kid. It was about Ted Turner, the legendary TV mogul. Before Ted was “Ted,” he had to make bold gestures to get his channels on cable television. In one instance, he barged into the office of cable giant, Telecommunications Inc., and offered to kiss the feet of its CEO.

I didn’t take notes while reading Ted’s story, but it got stuck in my brain and became part of how I thought. Without realizing it, I emulated Ted Turner to help my startup survive. These are the types of life-changing stories I want my interview guests to share with my audience.

Great interviewers are great storytellers. They lead their guests—along with the audience—on a journey of adventure, struggle, rebirth, and triumph. In other words, the best interviewers follow the Hero’s Journey.

The Hero’s Journey looks like this:

  1. A person we care about—our hero.

  2. The hero faces a problem or opportunity worth pursuing.

  3. They start their journey.

  4. Inevitably, the hero hits an obstacle.

  5. They find help from an aid or mentor.

  6. The hero improves and starts to succeed.

  7. But then a major battle emerges. The hero falls into an abyss.

  8. The only way to survive is to transform, so our hero becomes someone new.

  9. The transformation leads our hero to victory and self-actualization.

The Hero’s Journey is my go-to interviewing framework. Here’s how I map questions to each stage of the journey, along with hypothetical answers I might receive:

  1. A person we care about—our hero.

    • Question: What were you doing before you started your company?

    • Answer: I worked at a bank. I hated it. I used to listen to entrepreneurship podcasts, wishing I could do something like that, but I couldn’t do it. My family always had financial problems when I was growing up, and I wanted safety.

  2. The hero faces a problem or opportunity worth pursuing.

    • Question: What led you to start your business?

    • Answer: Then the 2008 financial crisis hit. My boss said to me, “You do a good job, but we can’t afford to keep you.”

  3. They start their journey.

    • Question: How did you deal with losing your job?

    • Answer: I tried to find a job, but no one was hiring. So I decided to try starting my own online business. I was always into journaling, so I created my own journal and sold it online.

  4. Inevitably, the hero hits an obstacle.

    • Question: Did you sell a lot of journals at first?

    • Answer: No, I didn’t sell any. I couldn’t get anyone to come to my site.

  5. They find help from an aid or mentor.

    • Question: How did you learn to sell?

    • Answer: I met an entrepreneur who figured out search engine optimization, SEO. He wrote blog posts using keywords that Google searchers were looking for. I didn’t have enough money to buy ads, but I had plenty of time, so I started doing what he showed me.

  6. The hero improves and starts to succeed.

    • Question: How did you finally get sales?

    • Answer: SEO took a few months, but eventually, I got customers. People searching for phrases like “journal ideas” and “how to start a journal” would see my site in the search results, click over to read my blog posts, and often buy one of my journals. The writing was pretty bad, but it worked on Google’s algorithms.

  7. But then a major battle emerges. The hero falls into an abyss.

    • Question: So after that it was easy?

    • Answer: No. I was too dependent on Google. They changed their search algorithm, and almost all my traffic disappeared, instantly. By then, the economy had improved, and I considered going back to look for a job, even though I knew it would make me feel dead inside to live that way again.

  8. The only way to survive is to transform, so our hero becomes someone new.

    • Question: Why didn’t you give up on your idea?

    • Answer: Actually, I almost did. I got a job offer for a bit more money than I made before I got laid off. But when it was time to accept the job, I started asking myself, “Do you want to be scared your whole life?” I decided that if I figured out SEO before, I could relearn the new way. And if I could learn SEO, I could figure out how to do social media, buy ads, and do other marketing things. So I stopped thinking about a job and started obsessing over self-improvement. It took me a year to get my site’s traffic back to where it was before Google’s algorithm change, but I did it.

  9. The transformation leads our hero to victory and self-actualization.

    • Question: How’s your business today?

    • Answer: Today, I get my customers from a mix of five different places. If Google changes its algorithm again or something else shuts down, it wouldn’t be the end for me. I have a real and sustainable business. I now know that everything in life is learnable. Now, when I feel I can’t do something, I know that I could learn it. It’s like a superpower.

No interview will follow the Hero’s Journey outline perfectly, and that’s OK. We’re not trying to script the conversation, just guide it. For a real-life example of the Hero’s Journey interview structure, listen to Mixergy Episode #2,122 with Andrew Gazdecki, founder of MicroAcquire.

Andrew is a startup hero in many people’s eyes: humble, hardworking, and fighting for the little guys. His journey closely maps with the Hero’s Journey, from a less-than-ideal upbringing to meeting a mentor, to selling his company for life-changing money. Now Andrew’s on a new journey—to change the way startups are bought and sold. His story is fascinating on its own, but it’s even more compelling because it follows that ancient Hero’s Journey framework.

You can use the Hero’s Journey framework for just about any interview, but it’s not the only structure you can follow. If your goal is to help your audience learn a new skill, use the next interview structure: the how-to.

Listen: Hero’s Journey Interview Structure

Interview Structure 2: How-To13 minutes, 6 links

Most interviewers guide their how-to interviews based on the questions they think up when they’re trying to learn the topic. That approach works fine, but it’s not the optimal way to teach something.

My how-to interview structure is so effective that I call those interviews “Master Classes,” and I charge for them. That’s because by the end of the interview, my audience will have acquired a useful new skill, like growing their website’s sales. But how-to interviews also take more work to put together. I can’t do these interviews well without an extensive pre-interview or doing heavy research.

In this section, I’ll show you how to prepare a how-to interview that’s so good, your audience will pay you to teach them. At the very least, you’ll know how to structure conversations to learn more effectively from experts you admire.

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