How to Conduct An Amazing Podcast Interview

As the buzz around podcasts has grown, everyone from the hobbyist to the biggest media companies in the world has hopped on the bandwagon. And there’s no shortage of advice, tactics, and hacks on how to launch, grow, and promote a new podcast. But, what is lacking is advice on how to conduct an amazing podcast interview. There are two fundamental skills at the heart of every successful podcast:

  1. Conducting interviews/asking great questions
  2. Telling a compelling story

Without these two skills, podcasters will drown in a sea of sameness noise. In a crowded media landscape, you have to focus on mastery instead of metrics. And you can’t hide shitty art behind great marketing.

The Critical Ingredient of Conduct an Amazing Podcast Interview

One of the most overlooked aspects of conducting an amazing podcast interview is choosing subjects. There’s a misconception that and fame and status is a good criteria. But it may actually be the worst criteria for choosing a guest.

Famous people are difficult to reach. They get asked the same question all the time and to top it off most people already know their stories. When you use fame and status as a filter for choosing interview subjects, you overlook the fact that everybody has a story worth telling.

Some of the worst guests in the history of our podcasts have been “famous.” They were so bad, we’d never have them back. On the flip side, some of our best guests were the people who nobody has ever heard of.

But it’s up to the interviewer to find the story inside their subject. Asking about someone’s accomplishments is a useless question. You don’t learn anything you couldn’t by reading their Linkedin Profile or bio. The lessons they learned will be far more interesting and valuable to you as an interviewer and to your listeners. The purpose of an interview isn’t to have someone recite their resume out loud.

Research and Preparation: The Double-Edged Sword

Conducting research on a guest is more of an art than a science. It varies from person to person. Too much research kills spontaneity. But if you don’t do enough research you won’t be able to have a good interview. People are always surprised to find that I do very little research on my podcast. I do this because it prevents me from using a scripted list, forces me to listen, and helps maintain spontaneity.

Read the About Page

When I go to someone’s about page, I’m far less concerned about their accomplishments. Who they are as a person is more interesting. I always look for something that’s unusual or interesting about them because that’s often where the seeds of a great story lie.

For example, Cal Fussman wrote a letter to Lyndon Johnson right after John F Kennedy was assassinated. That experience taught him that you could connect with the most influential people in the world by asking questions. His interview on Umistakable Creative was like a lesson in American history.

Read their book

I try to read the books of every person I interview. I can almost always pull off a great interview without reading the book. But reading their books leads to much more interesting questions. After reading each book, I take everything that I’ve highlighted and put it into Notion. That way I can ask about some of my favorite passages and quotes during our conversation.

Asking Interesting Questions

The ability to ask good questions is essential to a podcast. It doesn’t matter whether your format is interviews or narrative storytelling. Without goods questions, you don’t get good tape, and you can’t tell good stories.

Explore Your Own Curiosity

People joke that the guests on Unmistakable Creative are a reflection of the problems in Srini’s life. If that’s the case I’m a

All joking aside, I ask people about the things I’m curious about. I want to know what I’d never able to learn from reading a person’s book or bio. When your curiosity about another person is genuine, it’s much easier to ask interesting and provocative questions. But if you’re pretending to be curious about another person because of their perceived status, your questions will always come across stilted and canned. The person I’m trying to entertain most with my interviews is me. The result of that for us is a lineup of guests that ranged from bank robbers to billionaires.

Never Use a Scripted List of Questions

One of the biggest mistake new interviewers make is to plan ALL of their questions in advance. It’s good to have at least one question to kick things of. But if you have all of your questions in advance, it actually decreases the quality of the conversation. It sounds more like an interrogation than an interview.

If you’re just going through a list, you don’t even need the guest. You can have them record their answers and splice your questions in. And it’s mind-numbing to listen to a conversation with no spontaneity or room for exploration.

The biggest problem with a scripted list is that it prevents you from listening. Because I know I’m talkative to a fault, the only questions I know in advance are the first and last question. I come up with the rest of my questions on the fly.

If you watch surfers carefully while standing on the beach, you’ll see that they are always adjusting to whatever the wave is doing. Asking good questions is the same. The framework for this is simple it’s ridiculous.

  1. Ask a question
  2. Listen to the answer
  3. Ask a question about the answer you were given
  4. Rinse, wash, repeat

People are like onions. This framework helps you to explore them in-depth, one layer at a time.

Every Question Should Elicit a Story

Humans are hardwired for story. We can’t stop listening when someone is telling a story. Think about all those “driveway moments” you had when listening to NPR . You stay in the car just to finish hearing what they say. My old business partner Brian clued into this and had me make one simple change. He noticed that the best parts of the conversation were happening 20 minutes in. He realized we could get there faster just by changing our first question. He gave me the following list.

  • What birth order were you and how did impact you?
  • What social group were you a part of in high school and how did that shape your career choices?

With questions like this, you kill multiple birds with one stone: People can’t answer these questions without telling a story. And it’s a powerful pattern interrupt.

If you evoke an emotional response from a person telling a story, you’ll likely elicit an emotional reaction from the person listening.

Influential people get asked the same questions all the time. Because they are in the media so often, they usually repeat talking points. One of the first things I tell every podcast guest is to do the opposite of what media training teaches them.

20 minute answers are fine. I want stories, not soundbites and talking points.

If you can invoke emotions from your guest, your listeners will never “changed the channel.”

Shut up. Listen. Don’t Interrupt.

The cardinal rule of asking good questions is that silence is golden. But silence is also uncomfortable. Five seconds of silence can feel like an eternity. It’s tempting to fill in those spaces or interrupt. But if you resist this temptation, not only will your subject fill the silence. Some of the most poetic segments I’ve ever recorded happened right after what felt like an eternal silence.

There’s a difference between hearing someone and listening to them. You want to listen with the intention of learning, not to get to the next question on your list.

Entertain and Inform

Overlooking the fact that audio is an entertainment medium is the cardinal sin of online marketers who start a podcast. If you’re just rehashing what’s in a blog post, it defeats the purpose. If you want to ensure that people don’t change the channel, you have to entertain them

.This is part of the reason I never start our show asking about a guests book or area of expertise. By having them start with a story from their life, we’re able to entertain our audience. We shut off our guests logic, tap into their emotion. Then, they open up in a deeper way when we do get to their expertise.


One of the easiest and most valuable things you can do to improve your interviewing skills is to practice with family members. You’ll learn things you never knew about them and it might even change your relationship with them.

The week before my sister’s wedding, I decided to interview all of my family members using the StoryCorps app.

Not only did I get to preserve the stories of people who matter most to me. But I learned things about them I never knew. The conversations ranged from hilarious to heartwarming. My cousin Rama told me about the process of her engagement, which I turned into the animated short below.

Like most Indian mothers who have 41-year-old single sons, the bane of my mother’s existence is that I’m not married. But according to my friend, my dad is like the Indian Benjamin Button. He’s aging in reverse. So, I tell my mom ‘I’m going to age that well. Why are you worried?”Over the years we’ve had many fights about this. And some have almost done permanent damage to our relationship. But when I sat down to interview her, we could have this conversation with curiosity instead of judgment.

The last question I asked my mother was “are you unhappy that I’m not married.” What she said changed the way I saw the situation forever: It’s not that I’m unhappy. But, more than anything I worry about who will take care of you when we’re gone.

A simple question revealed that she had the purest of intentions all along. Don’t underestimate the power of interviewing your family members. It won’t just improve your interviewing skills. It might make your relationships better.

Humanize Your Guest

Even if they are the movers, shakers, billionaires, or moguls, they are still human. But so often, we put people on pedestals and overlook their humanity in the process. And because of this, they become less relatable to the person listening.


A person’s imperfections are more interesting than their achievements. It’s the first step to humanizing them. Oprah often asks people “what do you know for sure?” I take the opposite approach “what are you still uncertain about or afraid of?” There’s not one person I’ve ever spoken to who is free from imperfections or insecurity. It’s hard to trust anyone who appears to be perfect.


Even though I’ve never interviewed him, there’s one question I would ask Alexis Ohanian. What’s been the impact on your life of losing your mother at such an early age? How has having professional success at the same time shaped you?

You never ask questions like this with the purpose of putting someone on the spot. It’s important to respect their boundaries. Questions like these force us to see beyond the mask of their status on social media and a list of accolades.

Emotion-Not Logic

If you want to humanize an interview subject, you have aim for emotional responses to questions instead of logical ones. When you ask emotional questions, good stories, imperfections, and vulnerability are inevitable. When Cal Fussman interviewed President Gorbachev, he thought he would have an hour. But, they told him he only had 15 minutes.

He ditched his script and asked about the most important thing his father taught him. Thanks to the question, the President ignored the time limit. When you use emotional questions, you end up with driveway moments and repurpose podcast content into pieces like the below.

In his article about how to become a world-class interviewer, Barrett Brooks made the following observation:

Just about anyone can create an interview show. Grab the headphones that came with your phone, invite a friend to hop on Skype, hit record, and voilà, you’re a podcaster with an interview show. This is how we got so many interview shows and so few interview shows worth a single listen.

That raises the bar significantly. Becoming a world-class interviewer has nothing to do with marketing or metrics. It’s all about mastery. And unless you’re up for, that you’re just making noise.

Gain an Unfair Creative Advantage

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