How to Ask Better Questions in Podcast Interviews

Jovian Gautama
The Startup
Published in
5 min readMay 5, 2020


Photo by Matt Botsford on Unsplash

A podcast is a form of entertainment, no matter what the topic is. It can be education, self-improvement, marketing, engineering, or design, it has to be entertaining to keep listeners engaged.

If you are hosting an interview-style podcast with different guests every episode, getting great answers is the only way to hook your audience in.

To get high-quality answers, you have to ask high-quality questions.

Now, before we go into how to shape and ask interesting questions, let’s start with the basics first. Are you ready?

Do. Your. Research.

Seems obvious and straightforward enough, but it really is 80% of the work. If you half-ass your research, you’ll end up with the same dull questions 20 other podcasters have asked before.

Some places where you can start doing research about the guests:

  • Podcast interviews
  • Blog posts
  • Written interviews
  • Talks
  • Twitter
  • Publications

Once you’ve done your research, you can start molding the raw information you gathered to generate non-boring. Here are some ways to do that:

Add context to obvious questions

Usually, you invite someone to your podcast because the particular person has created, written, and shared about a specific topic or has a highly regarded expertise that your audience appreciates.

The next step is to ask the guest directly about it, but calibrate it so the answer can fit your audience even more by adding further context.

In my interview with Claire Lew on Outside the Valley, I asked her to talk about the three pillars of great leadership. To make it even more relevant to our audience, I followed up with the question:

Do you see leaders of remote companies as stronger at conveying these three points compared to non-remote?

My goal with this question was to help Claire elaborating on her insights, and at the same increasing the relevancy with our audience.

Investigate, then ask for details

Another way to dig interesting questions is to put your investigative journalist hat on. Find a specific thing that is not yet thoroughly elaborated anywhere, and use your podcast as the stage to explore it.

These questions open up the opportunity to dig into the finer details of the guest’s work. You’ll end up with unique questions never asked before.

Andrew Warner, founder of Mixergy, is a master at uncovering fascinating stories of entrepreneurs. He uses Wayback Machine to find old articles, and even reached out to ex-coworkers or friends of his guests as part of his research materials.

With this, Andrew can ask questions no one ever asked, and get stories no one ever heard.

How do you find the angles to dig into? My simple rule of thumb to spot potential stories is to listen closely to your brain when you’re doing your research. Is there any sentence, written or said, that makes your brain goes “Hm, I wonder why she said that?”

Whenever you find that opening, take notes, and investigate further to see if you can find the answer to that question.

If nothing comes up on your investigation, ask it in the interview. If you do found the answer and think it’s a valuable nugget for your audience, you can still ask the guest to share and elaborate on that.

Create a scenario

These are open-ended questions that invites the guest to apply their expertise in a specific situation. Concrete examples in form of scenarios can further establish the guest’s skills and reputation in your audience’s eyes — or in this case, ears.

The key to set up a killer scenario is specificity. When Seth Godin was interviewed by Louis Grenier on Everyone Hates Marketers podcast, here’s the situation Louis threw to Seth:

“We’re starting a business. We have let’s say $1,000 to spend and we have to be profitable in three months or less. The only thing that I’d like to set as a condition is that you cannot use your name at all. You have to remain anonymous so you can’t use your audience.”

Here’s Seth’s comment on that later on:

“That’s the most innovative, energizing way anyone has ever started a podcast with me.”

The lesson here? Specificity works.

Instead of talking about marketing theories, Louis set the stage for the interview to get real fast. It gives Seth stage to go deep into his business expertise in real time.

A good scenario should be tailored for your guest. You don’t have to come up with a unique situation for each one, but you can tweak the angle so it can apply to different segments of guests.

For example, if you are hosting a podcast about startup marketing, you can come up with different scenarios based on the guest’s position in the company.

If you want to listen to more examples of scenarios, Everyone Hates Marketers is a great place to start. Check it out. (Full transparency: Louis is a friend, but EHM is genuinely the only marketing podcast I listen to nowadays.)

Explore the intersections

Humans are multi-dimensional, and if you’re hosting an interview-style podcast, I’d assume you are interviewing — unless you are the host of Everything is Alive — well, humans.

Finding the intersections between different aspects of your guest’s background paves a way for authentic stories to surface. It created more dots to connect, and more fields you can explore and expand to.

Sahil Lavingia, founder and CEO of Gumroad is also a painter. Ryan Kulp, founder of Fomo and several other companies, is also a musician.

Instead of asking another general question about entrepreneurship or marketing, you can ask them about their thought process of how their art influences their business decisions.

There are tons of angles where you can find on these overlaps: The Chief Marketing Officer who is also a parent, the expert copywriter who is also an improv comedian, or the community manager who is also a social activist.

Get creative.

So, these are the methods I use whenever I’m prepping for a podcast interview. Some of them might be more suitable than the others depending on the premise of your podcast.

The key to all of this is: Find what works for you, and do it.

Happy podcasting!



Jovian Gautama
The Startup

Tech worker. Random thinker. Comedy fan. Editor and creator of Serious Tech News: