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Boring Questions, Boring Podcast: How the Best Interviewers Stand Out

Is your podcast boring?

I’m being serious.

Are you asking the same boring questions every other podcast host asks?

If you are, your podcast is boring.

Conducting a successful podcast interview is a skill you develop through practice.

Intentional practice.

The most popular podcast hosts were not blessed with an innate ability to ask intriguing questions.

They practice.

Many podcast hosts mistakenly believe going “Off the cuff” creates a more authentic broadcast.


James Altucher, Tim Ferriss, Mitch Joel, these podcast hosts approach every interview with a plan.

A lack of preparation is not authentic, it’s lazy.

As a podcast host, you have a responsibility to your audience. They listen to be educated, entertained and inspired.

Preparation, focus and practice are the only ways to deliver value with each new podcast episode.

LISTEN NEXT: The Ryan Hanley Show

Here are four tips extracted from a few of the best interviewers online:

Study Your Guest

The majority of the work that goes towards a great podcast interview is done weeks in advance of the actual interview.

Successful interviewers prepare.

You will not ask insightful and meaningful questions if you haven’t done your homework on your podcast guest.

James Altucher, among other accomplishments, has an incredibly successful podcast: The James Altucher Show.

james altucher podcast

James Altucher is an interesting guy. His diverse past and keen smarts create the foundation for a fantastic podcast.

But these qualities are not what separates James’ podcast from the field.

James prepares more than any podcast host (for sure any marketing/business podcast host) I’ve listened to.

And it shows in the questions he asks.

The average podcast host will Google their guest, skim through their latest book, check out their blog, and read their Wikipedia page.


James will buy and read their entire catalog.

He analyzes their LinkedIn page, reads every news article he can find, learns about their hometown, and watches/reads every interview that’s ever done.

Not only does this allow him to ask insightful questions the guest has never heard before, but also make connections between events other podcast hosts could never make.

When you see a well-known guest doing the rounds through the top podcast shows, you can always count on Altucher’s interview to be original.

James Altucher is an expert on his guests before he asks a single question.

This quality defines his show and sets it apart.

SEE ALSO: Starting a Podcast: 7 Things I Wish I Knew Before I Published My First Episode

Crowdsource Questions

Without your audience, your podcast is nothing more than audio recordings that you’ve uploaded online.

To grow a large audience that keeps coming back for more, you have to give them what they want.

Tim Ferriss’ podcast is not boring.

In part because Tim is one of the hardest working guys online. He also is deft at giving his audience exactly what they want.

For his podcast, Tim will ask his audience what questions they would like him to ask.

tim ferriss podcast

He doesn’t do this for every guest, but whenever he has an upcoming interview with a high-profile guest, like Arnold Schwarzenegger, he sends a tweet out to his audience asking what questions they would love to have answered.


The opportunity to have your question asked on Tim’s show creates anticipation and excitement. Not to mention the always elusive “Engagement” which is so vital to the longevity of a podcast.

If you’ve got a guest lined up that you know your audience is dying to hear from, why not solicit questions?

Maybe you give away a prize for every question that makes the show.

Asking your audience for suggestions is a guaranteed way to find out what questions they care about most and it can also help you brainstorm questions you wouldn’t have come up yourself.

WARNING: Don’t rely on your audience questions. They still expect you to lead the show. Otherwise you’re just being lazy.

Tim Ferriss finds ways to get his audience involved in his podcast.

This quality defines his show and sets it apart.


One of the biggest mistakes that podcasters make, especially when they’re first starting out, is not listening to their guests during the interview.

This is my number one pet peeve with podcasts. The bullet point interview. Also known as, the worst kind of interview.

I’m sure you’ve heard this type of interview before (some might call this a scripted interview).

The host asks a question and the guest gives a thought out response. You, the listener, are intrigued and ready for the host to dive deeper. But they don’t.

Instead, the host’s follow-up question is off on another topic. There is no flow and listening soon becomes frustrating.

The host can hear what their guest is saying, but they’re not listening to the response.

There are few podcasters as skilled at follow-up questions as Mitch Joel on his Six Pixels of Separation podcast.

six pixels of separation

Take your guest down the path they want to go.

Some questions will end up working out better than others. It’s hard to predict the ones that will get the most interesting answers beforehand.

But that’s the game.

That’s the work of being a podcast host, squeezing as much value as possible out of each guest.

Great interviews sound like an interesting conver­sation­, not an interrogation.

Creating conversations, not interviews, is the only way I’ve been able to separate my own show, The Ryan Hanley Show, from a competitive pack of content marketing podcasts.

To keep the conversation natural and interesting, you have to listen to what your guests are saying.

More importantly, you have to care what your guest is saying and ask questions which reflect such.

Mitch Joel listens to his guests.

This quality defines his show and sets it apart.

Stay in Their Sweet Spot

Unless your guest is a personal friend, they likely aren’t doing the interview solely for the sake of having a conversation with you.

Their time is valuable.

Assuming you do not pay guests, their compensation is being able to promote themselves and/or their work to your audience.

Michael Stelzner, host of Social Media Examiner’s Social Media Marketing Podcast, does an excellent job of this.

social media examiner podcast

It’s normal to set aside time towards the end of the interview to allow your guest to promote their latest project.

However, Michael likes to throw in questions throughout the interview which allow his guests to insert what they do into the conversation.

This is great for two reasons. The first one is that his audience wants to know what makes your guest special and why their insight is valuable.

The second reason is that we all enjoy talking about things that we know best.

These questions put the guest in their sweet spot.

You can tell when a guest is dialed in by the enthusiasm in their voice and pace at which they speak.

You don’t want to go overboard with these types of questions or your interview will sound too staged.

Done well, a track record of making your interviewees shine will make your podcast more attractive to future guests.

Michael Stelzner knows how to showcase his guests.

This quality defines his show and sets it apart.

The Rub

Every day the catalog of marketing podcasts on iTunes grows.

There are no schemes or tricks for long-term podcast success.

The podcast host must be laser-focused on delivering value every episode.

No one wants to believe their podcast is boring. But the truth is, if you’re asking the same questions as everyone else, your podcast is going to become stale.

Don’t settle for boring questions and boring podcast.

Answer this: How do you ask better questions?

Yours in strength,


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