38 Min Read • Retention

How to Become A Better Podcast Interviewer: The Hidden Skills, Traits & Practices Behind Truly Great Guest Interviews

A practical guide to improving your interviews, episodes, and guest relationships... and growing your show along the way.
By Jeremy Enns

By Jeremy Enns

By Jeremy Enns

More than 90% of people believe themselves to be above-average drivers.

More than 90% of college professors believe themselves to be above-average teachers.

And when it comes to podcasting, it’s not a stretch to assume more than 90% of hosts believe themselves to be above-average interviewers.

Over the course of more than eight years and hundreds of conversations with podcasters across every show format, genre, and niche, I can think of just two or three instances where one of them told me their interviewing skills could use some work.

In fact, whenever I ask about what they see as the strengths of their show, almost every host is quick to tell me that they get great feedback on their interviewing skills.

Having personally audited many of these shows, however, I can safely say this is rarely the case.

Most hosts are passable interviewers.

Some are solid, even genuinely good.

Very few are great.

And why should they be?

Interviewing is not a craft most of us have any education in. Neither is it a skill we’re likely to randomly pick up through osmosis.

What little we do learn of interviewing tends to come from the world from journalism, which, while it certainly has its place, is not relevant to the types of shows most of us are making.

On the one hand, for many shows—especially those in underserved niches—the host doesn’t need to be a great interviewer for the show to be worth listening to.

And yet…

For any show built around the interview format, it’s clear that better interviewers = better episodes = higher audience retention = faster growth.

But this begs the question…

What exactly does it mean to be a better interviewer?

Given how closely entwined the interview format is with podcasting as a medium, it’s shocking that there isn’t a clear, universally agreed-upon rubric of the skills, traits, and practices of truly great interviewers.

Which makes it hard—if not impossible—for all of us as hosts to improve.

If we don’t know our destination, after all, how are we supposed to get there?

Of course, every interviewer is unique.

As is their particular approach, skill set, and line of inquiry.

But that doesn’t mean there aren’t some foundational guiding principles that great interviewers have in common.

And while I’m in no way claiming to be a great interviewer myself, I’ve analyzed enough interviews—ranging from awful to awe-inspiring—to have identified a series of traits to develop and lean into—as well as some to avoid—to improve your interviews.

Before we get into the specific traits of great interviewers, however, it’s worth taking a step back to identify what makes for a great interview itself.

What Makes For A Great Podcast Interview?

When embarking on any journey, it always helps to have at least a general idea of your destination.

Our quest to uncover what it means to be a truly great interviewer is no different.

So before we zoom into the specific skills, traits, and techniques employed by effective interviewers, it’s worth zooming out to assess the final product.

Specifically, what makes for a fantastic interview episode from a listener perspective?

I’d argue great interviews have 7 specific traits in common, the first four of which we’ll cover today.

1. Great Podcast Interviews Have a Guiding Vision

While great interviews often have a casual, conversational feel, we as listeners also have the distinct sense—from the first minute onward—that the episode is going somewhere.

Scrappy Podcaster Erin Scott, host of Believe In Dog summarizes this desire perfectly:

“While the goal is to feel conversational, that doesn’t mean it’s just a conversation. I don’t want to listen to people just “shoot the shit” without feeling like there’s some point or purposeful journey that I’m being taken on.”

Angelique Lusuan, host of both The Italian Escape and The AI and Digital Transformation Podcast echoes the sentiment:

“Aside from bad audio, a bad interview (for me) is one done in a chit-chat friends’ format with no direction.”

Listeners want to know that they’re in good hands with the host and that their time and attention is being respected.

To that end, great interviews are built around a clear, pre-determined vision encompassing:

  1. Why this guest is being invited on in the first place
  2. The intended outcome the interview is working toward delivering for the audience
  3. The framing for the interview that contextualizes it in the listeners’ lives
  4. The specific questions being asked and the purpose of each

This isn’t to say that great interviews don’t branch off in unexpected but interesting directions.

In fact, that is one of their hallmarks.

But in the best interviews, those side journeys are always tied back to the main theme, creating cohesive episodes that build and maintain momentum toward the promised destination.

2. Great Podcast Interviews Offer Listeners Something Novel

This novelty can take many forms, but the most common are:

Novel Insight, Ideas, or Information — Which allows the audience to learn something new that they haven’t encountered anywhere else before.

Novel Anecdotes — Or, getting the guest to share something they’ve never shared before.

These take on added importance if your guest has been interviewed widely before, as, over time, your ability to consistently elicit original anecdotes can become one of your primary differentiators, and the reason people choose to listen to your interview of a specific guest versus any of the dozens of others.

But original anecdotes aren’t only valuable when interviewing well-known, widely interviewed guests.

Mediocre interview shows in every niche are filled to the brim with largely interchangeable guests sharing generic, same-y, anecdotes that not only fail to connect with listeners but drive them to boredom.

Regardless of the guest’s level of fame or recognition, great interviews surface interesting original anecdotes that are particular to the lived experience of that guest.

In other words, they feature stories that only that guest could possibly tell.

Erin Scott, of Believe In Dog articulates this desire for novelty clearly:

“For me, a great interview uncovers new ground or a new angle, especially if the guest is someone known to speak about their certain topic.”

3. Great Podcast Interviews Leave The Listener Changed

The best interviews create a clear before/after moment in the listeners.

That change may be as drastic as a listener wholly reconsidering their life priorities and trajectory after listening to an interview.

Or, it may be as small as reconsidering a topic they thought they knew and taking on a new, deeper, or more nuanced understanding or appreciation of it.

Regardless of the scope of change, listener transformation is at the heart of the most resonant (not to mention recommendable) interviews.

These are the interviews we remember for years, relisten to multiple times, and talk about with everyone who will listen.

4. Great Podcast Interviews Connect with the Guest’s Humanity

Podcasts are a fantastic way to absorb knowledge and information.

But their real strength (and advantage over more efficient knowledge transfer mediums like writing) is their ability to infuse information with emotion, humanity, personality, and nuance that creates content that is both useful… and deeply connective.

Unfortunately, the vast majority of podcasts ignore this opportunity entirely.

Hosts may keep the guest at arm’s length for any number of reasons, including concern about crossing a line into uncomfortable personal territory or veering off course from the show and episode’s topic.

Regardless of the cause, however, the absence of humanity creates flat, forgettable episodes—even when those episodes are filled with useful information.

Note that connecting with the guest’s humanity is not simply about recounting their life story.

It’s about pushing into the messy, potentially uncomfortable, human emotions, struggles, and conflicts that underpin their, your, and your audience’s experience with the topic at hand.

Nick Korte, host of Nerd Journey identifies this desired feeling of connecting to the guest as follows:

“I want to finish listening feeling like I got some great information from the discussion… but at the same time, wishing there was more time with the guest.”

5. Great Podcast Interviews Are Intimate

While there’s certainly something to be said about the intrigue and drama of heated, contentious, or outright combative interviews, these aren’t the types of interviews most of our audiences are looking for.

Rather, they’re looking for interviews that have a clear feeling of intimacy between the host, guest, and—by extension—listener.

Scrappy Podcaster Amanda Bennett, Founder of podcast outreach & guesting strategy company Gotcha Mama describes the feeling of great interviews as:

“You can feel the rapport with the guest and host. The host seems excited to be there and talk with the guest. There’s a good flow of back and forth – not a lot of one person.”

In these interviews, it’s clear that the guest has enough trust, rapport, and respect for the host to feel comfortable opening up, deviating from their standard talking points, and sharing more than they previously have.

Which, as a result, leads to more humanity, connection, original anecdotes & insight, and ultimately, potential for listener change.

There’s a fine line to walk, however, in building and maintaining intimacy with your guest while keeping the interview listener-oriented, true to your vision for the episode, and filled with sufficient tension.

Speaking of which…

6. Great Podcast Interviews Contain Tension

Anything interesting is built around tension.

Between what is vs what could be.

Between what we know vs what we don’t.

Between competing or contradictory approaches to a challenge or visions for the future.

Between an action and the anticipated result or reaction.

When present, tension pulls a listener through an episode, keeping them actively engaged as they wonder where the episode is going.

Sadly, most podcast interviews are hopelessly devoid of any form of tension, and correspondingly, interest.

In great interviews, tension is most easily (and deliciously) introduced by the host pushing:

  1. The guest in a certain direction — ie. To go deeper, get more specific, provide a concrete example or story, etc
  2. Back on something the guest said — ie. Challenging them, asking for proof, staking out a competing argument and asking them to reconcile it with their view, playing devil’s advocate, etc

Like any of us, podcast guests by nature will stick well within their comfort zone unless prompted (or challenged) to leave it.

But leave it they must for an interview to be truly valuable.

Erin Scott from Believe In Dog articulates a common frustration among podcast listeners:

“[I love interviews where the] guests don’t just stick to their talking points or tell the same 3 anecdotes they’ve shared on 57 different podcasts while promoting their book.”

In addition to pushing the guest to step outside their comfort zone, tension can be created by the host through Angular Questioning, changes in direction, and introducing surprise.

Angelique Lusuan, Scrappy Podcaster and host of both The Italian Escape and The AI and Digital Transformation Podcast describes the result of this kind of tension.

“For me, great interviews leave me with the feeling like I’ve been taken to a roller coaster ride I was not forced to or dragged by.”

Keep in mind that while tension is often built around some form of conflict, you don’t need to get combative with your guest to create it.

Episode- & insight-driving tension can be just as easily produced through gentle prodding, nudging, and clarifying as mic drop callouts and rebuttals.

7. Great Podcast Interviews Enrich Every Participant

In the best interviews, all three parties—the host(s), guest(s), and listeners—leave the experience feeling personally enriched.

We’ve already discussed how the audience should walk away with something novel they’ve never encountered, undergoing a change in some way.

But the host and guest should also leave the interview better than when they came in.

Often, this enrichment emerges directly from the tension so many hosts avoid creating.

Personally, all my favourite interviews as a guest were those where the host challenged me, pushed for specificity and concrete examples… which helped me uncover new ideas I would have never arrived at on my own.

Coincidentally, these are the guest episodes I am most excited to share with my audience.

The same dynamic plays on the host side.

While many hosts—eager to portray themselves as “experts” or “authorities”—shy away from questions or topics they lack deep knowledge in, some of the best interviews emerge from a host who is willing to put their ego aside and enthusiastically explore the guest’s expertise and experience.

What Makes A Great Podcast Interviewer?

Now that we know what makes for a great interview from a listener’s perspective, we could define a great interviewer is someone who facilitates great interviews by hitting these notes on a consistent basis.

But how exactly do they do it?

Based on my experience, it comes down to a specific cocktail of skills, knowledge, traits, and techniques they employ and embody.

Some of these are obvious and relate directly to the desired outcomes mentioned above.

Others are subtle but essential to the creation of meaningful & engaging interviews.

All of them, however, can be learned, adopted, and cultivated by anyone.

1. Great Podcast Interviewers Are Personally Curious About the Topic & Guest

There are few bigger listener turn-offs than a clearly disengaged host.

And yet, so many podcast interviews feel as though the host is simply punching the clock, interviewing guests simply because that’s what they think they’re supposed to do.

Great hosts, on the other hand, are brimming with eagerness, enthusiasm, and genuine curiosity, both about their guests, and the topics they are exploring.

To a listener, this energy is infectious.

What’s more, when combined with proper preparation and research, a host following their internal curiosity compass is much more likely to find their way into interesting topics and angles that haven’t been covered elsewhere.

The result is novel, differentiated episodes that leave the host, guest, and audience enriched.

That said, unbridled curiosity can easily lead to unfocused episodes, which is where vision comes in.

2. Great Podcast Interviewers Have a Vision for the Interview

This vision extends across multiple planes including:

  • Why this topic matters to their audience
  • Why this is the right guest to explore the topic
  • What is interesting & underexplored about this topic
  • The specific outcome the interview is working towards
  • The choice & sequencing of questions that will facilitate that outcome

A lack of vision makes for a frustrating listener experience, with loose, meandering episodes that lack forward momentum toward a destination.

It also results in episodes that are inherently hard to market, as they lack a clear, compelling hook or promise.

Great hosts have the vision for the hook and often even the title before they ever hit record, and in some cases, before they even find the right guest to fulfill it.

The result is a high “hit rate” of novel, differentiated episodes that both hold the audience’s attention and are easy to market… because they were designed that way from the start.

3. Great Podcast Interviewers Do Their Research

Amateur hosts often eschew any meaningful interview research and prep.

Perhaps they think coming in unprepared will lead to more “organic” or “authentic” interviews.

Perhaps they’ve heard that’s how Larry King did it and assume it will work for them as well.

More likely, they’re lazy and are simply looking for an excuse to justify it.

The truth is that proper research is not only of immense service to your listeners, it’s actually an essential enabler of deeper, more authentic interviews.

Good interview prep achieves 3 things:

  1. It wins the guest over by showing them that you’ve done your homework and are serious about the craft.

    Not only does this improve the energy they bring to the show, but it also provides a strong foundation of respect which is essential if one of your goals is to build relationships with your guests.

    Watch almost any episode of Hot Ones to see this principle in action.
  2. It shows you what topics and questions to either ignore and/or compress as they’ve already been covered extensively elsewhere.
  3. It uncovers interesting, novel, and perhaps unconventional threads to unravel or weave into your interview, either as primary themes or interesting accents.

While good interview research won’t guarantee a great interview, it will guarantee a novel one that avoids the same dozen questions the guest has answered on a dozen (or more) generic podcasts before.

That alone, is enough to make your interviews noteworthy.

4. Great Podcast Interviewers Are Low Ego

One of the most common complaints podcast listeners have about hosts is when they “make the interview about them.

This isn’t to say that the host should remove themselves from the interview altogether, however. Many of the best podcast episodes feature a balanced conversation between the host and guest with both making valuable contributions to the discussion.

The problem is when the host’s interjections and contributions are rooted in ego and insecurity.

We all have egos, of course. And we all want to be seen as smart, charming, funny, and likeable (especially if the purpose of our show is marketing for our business).

The problem is that while we often can’t see it in the moment, listeners can detect try-hard, insecure energy from a mile away… and then do everything they can to maintain that distance.

Great hosts are not immune from ego.

Rather, they have the self awareness to recognize their triggers—often by reviewing past episodes—and the confidence to suppress the inevitable urges to inject themselves into the interview when it’s not in service to the episode.

In fact, listen to enough great interviewers and it quickly becomes clear that the real flex is to have the courage to ask the dumb questions in service of your audience.

5. Great Podcast Interviewers Think In Themes & Patterns

The biggest aha moments in an interview never come from straightforward, linear questioning of the guest.

Instead, they come from connecting a specific topic or idea to another seemingly unrelated one… and then unexpectedly (and delightfully) weaving them together into a cohesive whole.

To achieve this, great interviewers have developed a keen eye for pattern and theme recognition.

The result is episodes with a regular dose of entirely novel insights and ideas and a show for which there is no substitute.

Intellectual ahas are just the start, however.

By recognizing particular aspects of a guest’s story and connecting them to larger, universal themes, the host is able to form an emotional bridge between the guest and the listener.

This makes for episodes that are not only interesting and engaging but highly resonant as well.

The basis for this ability?

A particular distribution of knowledge common among great interviewers, hosts, and creators.

6. Great Podcast Interviewers Have T-Shaped Knowledge

While great podcast interviewers are often legitimate experts in a small number of fields, they supplement that expertise with a high level of competence in many more (which are often entirely unrelated).

This combination of breadth and depth of knowledge allows them to ask intelligent questions on a variety of topics and connect disparate ideas back to the core topic of the show.

What’s more, knowledge is an enabler of curiosity and a refiner of intuition.

Which means hosts with T-shaped knowledge distributions tend to find their way into the more interesting, less explored nooks and crannies of a topic than their counterparts with only deep or wide knowledge.

Great interviewers tend to accrue this knowledge through obsessive consumption of vast amounts of information across a wide variety of topics, generally following their own personal curiosities, hunches, and fascinations.

This level of consumption is a trait that doesn’t get talked about enough but is the backbone of most great interviewers, and by extension, interviews.

7. Great Podcast Interviewers Obsess Over Pacing, Structure, and Sequencing

New interviewers tend to view, think about, and structure their interviews based on one dimension: The “content” of the interview.

Great interviewers, on the other hand, approach interviews from a multidimensional perspective.

In addition to the content itself, they obsess over the dynamics of how that content is presented, mapping out—and then adjusting on the fly—the interview’s:

  • Pacing — To build & maintain momentum and ensure a high level of Value Density.
  • Structure — To ensure the content makes sense, has maximum emotional impact, and maintains & regularly resets listener engagement.
  • Question Selection & Sequencing — Ensuring each question has a specific “Job” for the audience and/or the guest dynamic, and they are presented in the most effective order to maximize connection, emotion, audience learning, tension, and payoffs.
  • Hooks & Open Loops — To keep listeners engaged and curious about how the episode will resolve.
  • Signposting — To help listeners mentally navigate the episode without getting lost and ensuring the key points and connections between ideas are recognized and understood.
  • Emotional Variation — To provide emotional connection on multiple levels that deepen the audience’s connection to the guest, the host, and the show.
  • Narrative Arc — To subtly set up the content as a journey the audience is going on (even if the episode itself is not being presented explicitly as a telling of the guest’s story).
  • And more

What these interviewers understand is this:

Content alone isn’t worth much if you can’t present it in an engaging, compelling way that gets listeners leaning in and wanting more.

Much of this skill is developed through doing their own editing (more on that in a minute) and ruthlessly assessing each episode, noting down the areas for improvement going forward.

They also enlist regular, honest feedback from other expert interviewers and producers to identify the issues with their presentation that they can’t see themselves.

The result is addictive episodes that keep audiences listening and coming back for more.

8. Great Podcast Interviewers Are Performers

There is a distinct difference between being a part of a great conversation and listening in as a third-party

Great interviewers understand that a podcast interview is a production that is being put on for an audience, and within that production, they must adopt the role of a performer.

This doesn’t mean donning a persona or becoming a caricature of themselves, however.

Performance of this type is about making intentional decisions about how they use their voice and body language to set and shift the tone of the interview.

This “performance” can include their:

  • Energy level
  • Posture
  • Intonation
  • Enunciation
  • Tone & Timbre
  • Volume
  • Word choices
  • Use of pause
  • And more

I’ve worked with many indie creators and small business owners who were serious enough about the performance aspect of their shows that they took vocal training classes to improve their delivery.

You can get started on your own, however.

Pay attention to the way your favourite hosts use their voices and you’ll quickly notice: Their “podcast voices” are not the same as they (or any of us) would use in their day-to-day life.

This is the performance of podcasting that makes episodes feel polished and professional.

And much like two musicians can take the same piece of music and make it sound—and more importantly feel—radically different based on their performance of it, so too do great interviewers.

9. Great Podcast Interviewers Are Great Editors

While the best interviews begin with intentional preparation and structure, interviews are organic, unruly things that rarely go perfectly to plan.

Great interviewers understand and expect this, and embrace editing as one of the most important tools of the trade.

Knowing that the finished interview will be edited, they embrace the opportunity to probe a topic from multiple angles, in search of the most articulate or meaningful guest response and pull on threads that might just lead somewhere interesting, knowing they can cut them if they don’t.

In post-production they perform the typical polishing, cleaning up some of the awkward pauses, crutch words, and repetitions to improve the flow and pacing of the episode.

But that’s just the start.

More importantly, they make the (always painful) cuts to sections that—while interesting—don’t serve the core purpose of the episode or are addressed more succinctly elsewhere.

Always, they are thinking about Value Density and pacing, ensuring the episode never begins to drag.

SPN (5).png

Indeed, editing alone is enough to elevate a mediocre interview to a great one, simply by cutting out the unnecessary, slow, low-value sections and leaving the gold.

While generally overlooked, editing is perhaps the single most powerful tool in all creative work, and great interviewers make steady use of it in their craft.

10. Great Podcast Interviewers Find, Expand, and Introduce Tension

Nothing keeps an audience engaged like tension.

And while the specific source of this tension can vary, all tension boils down to the same thing…


  • Uncertainty about how a situation will unfold or a person will react.
  • Uncertainty between which of two competing views or ideas is correct — or how they can be rectified.
  • Uncertainty about what we should do when presented with a choice.

Uncertainty is gripping.

The fact that we don’t know what’s coming next—let alone the outcome—is precisely what makes sports, games, gambling, art, well-told stories, and indeed life itself interesting.

And it’s the utter lack of uncertainty—and therefore tension—that hamstrings nearly every podcast interview available.

Listen to 10 interviews of any reasonably well-known guest and this dynamic becomes immediately clear.

Almost every interview is made up of the exact same set of expected questions, which result in expected answers, expected takeaways

The result?

Wholly unsurprising, undifferentiated… not to mention emotionally and intellectually unsatisfying episodes.

As a listener, it feels like these hosts are simply overseeing a series of assembly lines, each applying a different coat of paint but ultimately all working off the same interview blueprints.

As a host of an interview show, these blueprints might help you build a streamlined production process, but they will not help you build an audience.

The good news is that the bar for tension—and thus audience intrigue—in podcasting is so low, it’s not hard to stand out… if you’re willing to get a little uncomfortable.

5 Layers of Tension to Inject

In a typical interview, tension tends to emerge in five distinct ways:

  1. A promise or question made by the title, description, and intro that the episode pledges to resolve
    🤔 Tension: “Will the episode pay off the promise satisfactorily?”
  2. Stories and anecdotes that are used to illustrate the concepts and ideas the episode explores
    😮 Tension: “How is this going to end? How does it tie into this topic?”
  3. Unexpected questions or hypothetical scenario prompts that the guest doesn’t have a prepared answer for, that they must react to on the spot
    😬 Tension: “What are they going to do??”
  4. Requests for specificity or examples, or proof that push the guest to clarify vague or fluffy concepts and make them more concrete
    🤨 Tension: “Is this guest legit, or are they just another smooth-talking huckster?”
  5. Direct challenges to a quote, belief, or idea the guest has shared, especially when accompanied by a compelling rebuttal
    🌶️ Tension: “Ohhhhhh things are getting spicy!”

As you move down the list, the amount of tension—and thus audience intrigue—each tactic injects increases.

But so too does the level of discomfort the host must endure to introduce it.

Which is exactly why so few shows contain any type of meaningful tension.

In many cases, the hosts are unwilling to risk rocking the boat—especially if the guest is someone they perceive to be of higher status than themselves.

While understandable, this logic is based on two assumptions:

  1. That pushing on or challenging the guest in any way inherently means being aggressive or combative, thus alientating the guest
  2. That guests don’t want to be challenged or veer from their talking points

These assumptions couldn’t be further from the truth, however.

Curious Not Combative Interviewing

Left to their own devices, any guest will generally revert to the simplest, most top-of-mind answer to a question.

More often than not, however, that easy automatic answer isn’t all that insightful or interesting.

As the host, it’s your job to guide them deeper, towards a more helpful, more interesting, and perhaps more honest answer.

This isn’t achieved through direct confrontation, but by gently nudging them to go deeper, expand on their statements, clarify details, provide specific examples, and more.

The goal of this probing exploration isn’t to produce some sort of “gotcha!” moment.

It’s to explore the nooks and crannies of the topic in a way that is of service to the listeners.

As it turns out, this kind of exploration often benefits the guest as well. Which is why truly good guests are more than happy to engage in a dynamic conversation that attacks and defends its way to interesting new insights for everyone involved.

Good Guests Relish A Challenge

Contrary to what most hosts think, truly great guests are eager to be pushed on their thinking.

The reasons are simple:

  1. They know that being challenged on their thinking… and then making a strong defense or counter-argument makes them look better to the audience.
  2. They know new ideas often only emerge through the collision of ideas with reality and are always eager to make new discoveries related to their topic through a conversation or debate.
  3. Since they care about their craft, they are actively seeking gaps in their thinking so they can fill them and strengthen their core assertions.
  4. It’s really boring to give the same interview a dozen times and they’re often as desperate to approach their topic from a refreshing angle as listeners are.

As a guest, all of my favourite interviews have been those where the host challenged my thinking, presented me with hypothetical scenarios, and forced me to react in the moment.

In these cases, I left the interviews with not only a ton of respect for (and often a budding friendship with) the host, but also a list of new ideas to create content around.

On the flip side, one of the biggest red flags for a guest is someone who insists on sticking to their talking points, resists all prompts to clarify their statements, and bristles at the slightest challenge to their thinking.

This is not a guest who will do anything positive for your show… and is likely not a true expert, which means you shouldn’t be featuring them in the first place.

Ratchet Up The Tension

The tactics discussed here are valuable devices to introduce more tension into your interviews.

But they work best when used to tap into an existing tension that exists around the guest and/or the topic in the minds of either you or your audience.

Or, said differently…

If there’s nothing about the guest and their approach to the topic that you or your audience have unresolved questions about (or even flat-out disagree with) you probably don’t have the seeds of a great interview.

Respectful discussion, debate, and disagreement have been the foundation of progress in every field for millennia.

Which means if you’re serious about furthering the conversation and uncovering new knowledge in your field, they—and the tension inherent in using them—are some of the most valuable tools at your disposal.

Use them.

11. Great Interviewers Design An Intentional Guest Experience

When thinking about interviews, hosts tend to focus the majority of their attention on guest outreach, research, and the questions themselves.

What often gets lost in the mix, however, is the guest experience.

And yet, the experience you create for a guest has an extraordinary impact on the depth and quality of the interview.

Picture two scenarios:

  1. A guest receives a generic templated interview pitch about a generic topic the guest has spoken about on 13 other (generic) podcasts. They sign up for the interview and are then presented by a series of automated, de-personalized onboarding steps. At this point, they can tell they’re just another warm body to feed into the host’s content machine.
  2. The guest receives what could only be a 100% personalized email pitching them to come on the show to talk about a topic closely related to them and their work… But it’s from a totally unique angle they’ve never discussed before. Already, it’s clear the host has done some research, is familiar with them and their work, and sees them as a unique and fascinating human with something unique to share.

The guest might agree to both pitches, it’s free exposure after all.

But which experience do you think will result in the better interview?

If the goal is intimate, engaging interviews that connect the audience with the guest and uncover novel anecdotes and insights, connecting with your guests is every bit as important as the questions you ask them.

And as we can already see, that connection begins well before the interview starts.

Nailing Your First Impression

If you were trying to give your guests the worst possible first impression, here’s a good way to do it.

Send a cold pitch with a generic template email (yes, everyone can tell it’s a template no matter how much “tweaking” you’ve done), asking them to speak about an obvious topic they’re widely known for and have been interviewed on dozens of times before.

At this point, everything about this screams, “I don’t care about you enough to do any real research or come up with a unique angle that you haven’t already covered before.”

Again, they might agree to the interview, but there’s zero chance they’re going to share the episode.

Here’s a better approach.

Start by following the guest on social media and reply to their posts regularly. Even better, share their posts with your audience along with some thoughtful commentary.

If they have a newsletter subscribe to it. Then reply to their emails every so often.

Keep this up until you’re familiar enough with their work well enough to know what they talk about regularly (ie. everything you want to avoid or briefly summarize) and—more importantly—what they don’t… but would be interesting to hear their perspective on.

Then—and only then—is the time to pitch.

By this point, you should have had several interactions with them, meaning they’ll already have some recognition of you as someone who knows and appreciates your work.

Which means they’ll almost certainly open and read your pitch email.

Paired with an original interview angle, you’ve almost certainly got their attention at this point, and perhaps even their excitement.

But the real guest experience is just beginning.

Communicating Legitimacy

Once a guest has received your pitch, their next step will be to click through to your show.

Like any potential listener, the first thing a potential guest will see is your show’s packaging, including the cover art, show title, show description, and past topics.

Within 3 seconds of seeing these elements, the potential guest has likely already made up their mind about whether this show is the type of show they would guest on, based on the perceived quality, legitimacy, and audience of the show.

If the initial packaging passes the test, they may dig further, using past guests, production quality, and quality of questioning in past interviews to decide whether the show is worth their time.

Much like a new listener, this decision-making is happening entirely subconsciously, based on the limited amount of information your packaging provides them.

This is one more reason why the value of investing in clear, legitimate, professional packaging can’t be overstated.

Guest Onboarding

Once they’ve agreed to come onto your show, great hosts create an onboarding experience designed to set the guest’s expectations of quality, thoughtfulness, and intention.

In some cases, this might be achieved through a live 15 or 30-minute pre-interview connection call to get to know the guest and chat over logistics.

But it can also be done asynchronously.

Regardless of your process, your goal at every guest touchpoint is simple:

Communicate that you value your guest as an individual and that you are putting in the work to make this interview the best it can be.

Maybe you send each guest a personalized video (and bullet point text summary) explaining the show format, audience, topics you’d like to explore, and anything else they should know.

Another option is to get their input on the construction of the episode, by asking:

  • What they always get asked about that isn’t worth covering in more depth
  • What never gets asked about that they think matters
  • If there are any new ideas they’re working on that might be fun to dig into and explore
  • If there are any stories or anecdotes that always do well
  • What their favourite existing interview was and why
  • What would make this interview one that they would be excited to share

Note that your goal is absolutely not to get the guest to outline your episode for you.

Nothing signals host laziness more than an onboarding form asking the guest to fill out all the questions for you to ask them.

Sure, these types of shows are easy to create, but there’s nothing appealing about them from a listener perspective.

What’s more, this approach send a clear signal to both the guests and your listeners that you are actively trying to put in as little work as possible… which is not an attractive quality.

Instead, your goal is to combine your guest’s responses with your own research to end up somewhere novel and interesting to you, your guest, and your audience.

On Air Experience

A thoughtful pitch, legitimate packaging, and personalized (at least in part) onboarding set the stage for a great interview. But it will be capitalized on—or undermined—by the on-air experience your guest has with you.

Depending on the tone and topic of your show, the experience you create will differ.

An interview venturing into deep, perhaps uncomfortable emotional territory requires a very different guest experience compared to one revolving around high-energy tactical tips and takeaways.

With that in mind, the on-air environment to create may change from guest to guest, depending on your intended interview outcome.

Regardless of your destination, however, it’s essential to understand that guests take their cues from you.

Part of this may have already been established in the pre-interview info you sent them.

Part of it might come during the chat before officially starting the interview.

But most of it will come from how you show up on the show.

If you bring the energy and enthusiasm, your guest is more likely to match it.

If you make verbal mistakes and stumbles and laugh them off, your guest is more likely to feel comfortable doing the same.

If you ask surface-level questions, your guest is more likely to give surface-level answers.

If you share vulnerable stories your guest is more likely to do the same.

The list goes on, encompassing cursing, formality, humour, tone, depth, and more.

You set the tone and chart the course for the interview. Which means if there’s a destination you have in mind, you need to lead the guest there.

It’s worth noting that the tone, emotion, and energy you set for the interview can (and should) shift throughout the interview.

Great interviews are like music, rising and falling in rhythm and intensity.

Great interviewers are the conductors, intentionally modulating their tone, vocal inflection, pacing, and energy to guide the guest—and with them the interview—to their intended destination.

The result is dynamic interviews that not only pave the way for original insights and anecdotes the guest has never shared before—but also create a memorable experience they are vastly more likely to talk about and recommend.

It’s no secret that the gold standard for most interviewers is to have the guest respond to a question with “No one’s ever asked me that before!”

Perhaps a better goal is to have guests leaving the interview saying “No one’s ever given me an interview experience like that before.”

12. Great Interviewers Ask Good Questions

When you think of what makes a great interview, the quality of the questions is likely the first thing that comes to mind.

And it’s true, the best interviewers ask great questions.

But to understand how they do it—and how we can ask better questions ourselves—we need to take a closer look at what exactly makes a great interview question.

What Makes A Great Podcast Interview Question?

“That’s a great question.”

If you listen to interview podcasts, you’re probably sick to death of the phrase by now.

The phrase is most often delivered as a knee-jerk response by a guest… almost always to a decidedly uninteresting question.

Maybe the guest is buying time to formulate their thoughts.

Maybe they’re trying to flatter the host.

Or maybe they’ve simply listened to too much Joe Rogan.


Whatever the reason, the phrase has become ubiquitous to the point of becoming a podcasting meme.

No matter how disingenuous the response, however, it does beg an important question:

What exactly is a great interview question?

Every question—not to mention the guest, topic, and specific scenario it’s being asked in—is unique, of course.

But there are certain questions that deliver more insight and elicit better stories than others.

And while the specific questions may differ, great questions tend to fit into one or more question categories.

Once you recognize the hallmarks of a great question, you can identify and insert more of them into your interviews and beef up the quality of your episodes—and show as a whole—in the process.

Three quick notes before we dive in:

  1. Few if any questions will embody all of the traits listed here. But they don’t need to. A question fulfilling any one of these traits is generally enough to be solid if not great.
  2. Not every question in an interview will/can be a great question. Aim to ask as many great questions as possible, but don’t put too much pressure on yourself if every one isn’t a banger.
  3. This list is a starting point. If you have additional insights on what makes a great question, hit reply and I’d love to add them to the list with a link to your show.

Let’s dive in.

1. Great Questions Are Strategic

Beneath the surface of every interview, a hidden chess game is taking place.

With each question, the host moves a piece across the board and the guest reacts, moving one of theirs in response.

One of the most subtle but important roles a question can play, then, is as a strategic, intentional move by the host to either “attack the topic” from a specific angle, or maneuver into a position to set up an upcoming sortie.

The goal of this attacking is not to “win” against your guest.

The goal is to break through the natural tendency we all have to answer questions in the easiest, most top-of-mind (and thus generic and conventional) way possible.

If you want to elicit original insight, knowledge, and emotional depth, in your interviews, you, as the host need to do better.

In practice, that means knowing the endgames you’re working toward, and then setting up a series of questions that will lead you there.

If you want to discuss a topic that requires a guest to be vulnerable, for example, you need to lead them—through a series of previous questions—to a place where they feel comfortable being vulnerable.

Great questions, in this case, might be a series of (potentially uninteresting) questions that build rapport and intimacy with the guest in preparation for the bigger question that delivers the payoff.

There are many other strategic motivations to consider, however, including:

  • Character building — Including helping us as the audience understand who the guest is, what their motivations are/were, and how we relate to them
  • Scene building — To make stories and anecdotes more visceral, resonant, and memorable by surfacing specific details that help the audience visualize them
  • Shifting the energy of either the interview or the guest to:
    • Reset waning energy
    • Shift the level of tension or intensity
    • Try a different tack with the guest who isn’t giving you what you were hoping for
    • Etc
  • Connecting with the guest — Building rapport and intimacy that will either make the overall interview better, or allow you to take them in a certain direction
  • Offering necessary context — That the audience needs to make sense of the direction you want to go.

Great strategic questions may not look like great questions on the surface.

What makes them great is their tactical role in guiding the overall interview to the intended outcome.

2. Great Questions Are Driving

When writing a novel or screenplay, writers know that every scene must move the plot forward.

Great interview questions do the same, driving the conversation forward and building momentum.

This isn’t to say that every single question should be of this variety. But at least every 5-10 minutes you should include a question that moves the plot forward.

3. Great Questions Are Well Timed

Like a great joke, a great question is highly dependent on timing.

A fantastically insightful question delivered at the wrong time—either because it hasn’t been informational or emotionally set up—can fall flat and fail to elicit a meaningful response.

With that in mind, great interviewers maintain their list of areas they want the interview to explore, but keep their sequencing fluid.

Rather than stick to a rigid script, they attune themselves to the guest’s energy, enthusiasm, and responses, and choose their spots wisely.

Sometimes, this means waiting to ask a big “set piece” question at the moment of maximum emotional impact.

In others, it’s interjecting with a seemingly small clarifying question, follow up, redirection, or request to zoom in on something the guest glossed over but which piqued the host’s curiosity.

4. Great Questions Are Novel

Listen to 10 interviews a given guest has given on 10 different shows and it’s almost guaranteed that 90% of the questions will be near-identical.

If you’re the host of one of those shows, this is a surefire way to guarantee you’ll never grow.

Part of the appeal of great interview shows is that they ask novel questions that other hosts aren’t.

Jay Clouse from Creator Science is a fantastic example of this.

The first episode I listened to of his show was his interview with Seth Godin.

At the time I listened, I had already:

  • Heard Seth interviewed on dozens of other shows (including by heavyweight interviewers like Tim Ferriss and Debbie Millman)
  • Listened through Seth’s entire podcast back catalogue of 100+ episodes
  • Read more than a dozen of his books
  • Voraciously consumed his daily newsletter

And yet…

Jay asked Seth a series of questions I had never heard Seth asked before, and I was immediately hooked on Creator Science.

The next episode, with James Clear, Jay repeated the feat.

Safe to say, if Jay could find novel questions to put to two of the most interviewed people on the planet, you can achieve the same feat for any of your guests.

5. Great Questions Are Unexpected

It’s tempting to structure an interview as a linear exploration of a topic, with each question building on the last.

And while this sequencing can certainly work, it can also lead to monotonous, predictable interviews.

Many of the best questions are great precisely because they disrupt the flow, breaking the pattern and taking the audience—and the guest—somewhere they weren’t expecting.

I think of this approach as Angular Questioning.

Angular Questions are unexpected due to their timing or contrast (emotionally or topically) to the previous topic.

Another category of unexpected questions are those that the audience (and guest) would never have thought to ask themselves—even if, in hindsight, the question was a natural extension of the conversation.

These non-obvious questions are often those that lead to the greatest insight.

And while they can emerge as reactions to something the guest has just said, more often the most incisive, insightful questions are the product of the host’s research.

Specifically, they emerge from the host’s ability to read between the lines of the guest’s existing work and identify the blank spots on the map that are ripe for exploration.

While average hosts tend to ask questions based solely on the guest’s publicly available work and knowledge, great hosts look for the negative space in the guest’s life and work as the basis for their lines of questioning.

The result is unexpected, novel questions that (happily) surprise the guest and lead to rich anecdotes and responses they’ve never shared elsewhere.

6. Great Questions Are Personal

A few rare questions are great because of their broad utility in eliciting meaningful responses from every guest, even when the question is phrased the same way to everyone.

Krista Tippett’s opening question to every episode of On Being, some version of “Tell me about the religious or spiritual background of your childhood” is one of these rare gems.

Most great questions, however, are questions you might only ask to that specific guest.

Formulating these types of questions takes research and a genuine sense of curiosity. But the rewards—in connection, resonance, specificity, vividness, and insight—can’t be matched by generic questions that could apply to anyone.

7. Great Questions Are Muscular

The best stories impact and stick with us because of the layers of meaning they contain.

Great questions are the same.

These types of muscular questions do some heavy lifting by weaving layers of subtext into a single question.

These questions do double (or triple) duty by serving multiple purposes, including:

  • Providing tactical information
  • Establishing the character of the guest
  • Building out the scene
  • Speaking to a deeper, more resonant emotional truth or theme
  • And more

There is a time and a place for blunt, direct, single-layered questions. But the more work each question does for you, the more value-dense your interviews will be.

8. Great Questions Challenge The Guest

Having listened to thousands upon thousands of podcast interviews, I can say the following with absolute certainty:

The single greatest (and most common) shortcoming in podcast interviewing is hosts’ unwillingness to challenge their guests.

As discussed previously, tension is an essential component of engaging interviews.

No tension, no intrigue, no reason to keep listening.

And while structure, question sequencing, and topic framing all play an important role in creating and building tension, there is no more visceral form of tension than a direct challenge to the guest.

Challenging doesn’t (necessarily) mean confrontation, however.

Challenging a guest comes in many flavours, from playful banter to a gentle push for clarification to a direct rebuttal of a statement to a question calling them to account for their actions or beliefs.

Challenging a guest is almost always uncomfortable. But that doesn’t change the fact that it is the foundation of the best interview questions.

The reason is that the heat and pressure of a challenging question is where new ideas are formed and existing ideas are refined and crystallized.

Which means challenging your guests is one of the most valuable services you can provide to your listeners.

Here are some of the best ways to challenge your guests in a way that serves your listeners and makes for compelling interviews.

Clarify Fuzzy or Fluffy Concepts Through Concrete Examples

Subject matter experts have a natural tendency to speak in abstract terms.

The reason is often because they don’t want to speak about a topic in a way that is too specific to apply to the entire audience.

This well-meaning intention is misguided, however.

One of the most valuable ways to challenge your guests is by pushing them to translate the conceptual into the concrete.

This can be done either by pushing for more specific details of a concept or by asking for concrete examples of how they or others have applied it and the results it created.

Prompts: “What do you mean by that?” “What does that look like in practice?” “Can you give an example of how you would apply that?” “How do you apply this in your own life?”

Play Devil’s Advocate

A huge part of the value of an interview is the interplay between competing ideas.

Even if you agree with the guest’s ideas, playing Devil’s Advocate—especially in response to a particularly lofty or idealistic assertion—can help them clarify and strengthen their argument further, as well as provide your listeners with an alternative perspective.

Prompt: ”So that all sounds really great in theory. But what about…?”

Hypothetical Scenarios

When it comes to expert interviews, the guest’s thought process is usually more valuable than their knowledge.

Rather than asking questions to get the guest to share what they know, a more valuable approach is to present scenarios that get the guest to show the audience how they apply what they know to a situation that the audience is currently facing.

This 5-minute masterclass from Louis Grenier of Everyone Hates Marketers, challenging one of the most well-known, widely loved marketers on the planet, is a prime example of this technique in action.

Prompt: ”Imagine you’re in [situation] and you’re looking to [goal]. Walk me through your approach.”

Present A Counter Argument

An interview without disagreement is almost certainly a boring interview.

If you’ve done your research you’ve hopefully come up with at least a few points where you disagree with—or at least question—your guest’s stance.

If you’re asking good questions and thinking critically, similar scenarios will arise in every interview.

And when they do, you should lean into them.

These disagreements are invaluable discussion points that help your audience achieve a more nuanced perspective on a topic that might otherwise feel one-dimensional.

Prompt:”I don’t know that I entirely agree with that, because in my experience _____________. What are your thoughts?”

Make Assumptions

Specifically, assumptions you know to be overly simplistic or even outright wrong or misleading.

By making these assumptions, you then force the guest to clarify their position, feelings, or previous statements, adding more depth and specificity.

Howard Stern is a master of this technique as illustrated in this clip with Lindsay Lohan.

Here’s how he frames just a few assumptions, each of which then presents Lindsay an opportunity to confirm, correct, or clarify.

  • “…it had to be confusing…”
  • “…you probably needed…”
  • “…it’s hard to have a serious relationship with he’s so f*cking good-looking…”

Prompt: “Ok, so you’re saying that [intentionally overly simplified assumption], am I getting that right?”

Rectify Opposing Statements or Beliefs

Each of us contains multitudes, holding beliefs and taking actions that appear on the surface to be contradictory… but make perfect sense to us.

Or, perhaps we’ve never noticed the conflict.

Regardless, identifying and digging into these contradictions is one of the juiciest ways to challenge your guest, in a way that is clarifying for both them and your audience.

Most topics (not to mention people) defy easy accounting and categorization, after all, and it’s only by digging into the nuances and contradictions that we can begin to truly understand them.

Prompt: ”So earlier in the interview you mentioned ____________. But I’ve heard you say before that _____________. Those two ideas seems to contradict each other, don’t they? Or am I missing something?”

Give Them Something to React To

One of the most engaging ways to engage both your guest and your audience is to present them with something unexpected for them to react to

The thing you present could be anything from:

  • Something they’ve previously said or done
  • An idea or opinion from someone else
  • A new piece of information
  • A “prop” — like a visual or object
  • And more

The specific prompt or desired reaction can be similarly varied including:

Jon Youshaei, host of Created is a master of this technique.

In his interview with tech YouTuber Marques Brownlee, Jon frequently presents his guest with thumbnails, tweets, and even transcribed scripts Jon has pulled from Marques’ video for him to explain, break down, and otherwise react to.

He does the same in his interview with Mr Beast, presenting frequent examples of storyboards, video clips, thumbnails, video concepts.


Ask Questions the Guest Doesn’t Know the Answer To

The majority of podcast hosts formulate their questions around topics that are firmly in the guest’s wheelhouse.

The logic is simple: “The guest knows a lot about [topic] so I’m going to ask questions to transfer their knowledge about [topic] to my audience.”

Depending on the goal of your show, these types of questions might make up a significant portion of your interviews.

But they shouldn’t make up the entire interview.

The reason is that these questions are obvious commodity questions the guest gets asked on every single podcast they guest on. They don’t challenge them, elicit novel information or anecdotes, or do anything to differentiate your show from any of the other interviews the guest has given.

A better approach is to regularly ask questions that the guest doesn’t know the answer to.

This doesn’t mean asking pub trivia-style questions, mind you.

Instead, it’s about asking questions that you suspect the guest hasn’t thought much about but might have an interesting take on when put on the spot.

Like hypothetical scenarios, the value of these questions is in surfacing the thought process and character of the guest rather than rote information.

Hosts tend to avoid these questions because they don’t want to embarrass their guest by springing something unexpected on them that they struggle to answer.

It’s often the struggle to come to and articulate an answer to an unexpected question, however, that is most valuable.

Don’t shy away from them.

Pointed Questions

The last type of guest challenge is the one we most often think of: Direct, pointed questions.

These types of questions put the guest on the spot, and while they can be uncomfortable, don’t need to be confrontational.

Take this example, again from Jon Youshaei’s interview with Mr. Beast, where he asks his guest to share a recent disagreement he had with his business team and how it was resolved.

On the surface, the question feels a little invasive, and we can see Jimmy (Mr. Beast) squirm a little as he thinks through his answer.

This squirming is the sign that you’re onto something with a given question.

Every interview should have at least one question that will make your guest squirm.

A good test for this type of question is whether or not the idea of asking it makes you squirm.

This squirming feeling is the sign of a question that is getting at something real, emotional, and not often talked about publically… which is exactly the type of response we’re all looking to get.

Challenge Clarifies, Crystallizes & Captivates

Any idea or story worth spreading should be able to stand up to the crucible of challenge.

In fact, it should be strengthened by it.

Because if it falls apart under cross-examination, is it really something you as a host want to be perpetuating?

I don’t think so.

Beyond ensuring that your content is legitimate, challenging guests creates better content by surfacing new ideas, clarifying old ones, and introducing tension that draws listeners in and keeps them engaged, wondering what will happen next.

In a podcast ecosystem filled with tepid interviews made up of softball questions, turning up the heat is one of the easiest, fastest, and best ways to stand out.

Great Interviews Aren’t Made Overnight

Over the course of this guide, we’ve explored an extensive list of elements that must come together to create a great podcast interview—and become a great podcast interviewer.

I won’t lie, it’s ​an overwhelming list.

But that’s kind of the point.

The mark of any great artist is that they make the impossible appear effortless.

Great interviewers are no different.

The magic of a great interview is that we as the audience are unaware and undistracted by the hours of editing, days of prep, weeks of guest outreach, and years of skill-development and networking that have gone into creating a single 45-minute interview that impacts us in a meaningful way.

Not to mention the hundreds of interview reps the host has under their belt.

Which is exactly where each of us must begin.

This guide provides a map of the terrain that is open to you to explore in your quest to improve your interviews—and your show.

But it’s up to you to do the exploring.

By building up your reps, guest by guest, interview by interview, question by question.

Start Growing Your Show— Here’s How

Enter your email address below and I’ll send you a 6-lesson course walking you through how to set your show up for long-term growth that doesn’t require you to spend all your time marketing.

No spam. Ever. That’s not the kind of marketing we practice, teach, or tolerate. Unsubscribe at any time with a single click.