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Want 5 quick ways to improve as a podcast host or guest?

Elevating Your Podcast Guest Interview Game to Build Stronger Connections and to Achieve More

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How are you doing in podcasting as a guest, host, or both?

Every podcast host knows you have a reason to be on their show, but do you know theirs? By tapping into the motivations and business models behind a show, you’re able to take the host and audience to new places that they all secretly want to go. In this post, Dan Cumberland shares his strategy for flipping the script on guesting to allow you to bring more value, build better connections with hosts and audiences, and get more out of each appearance!






Read the Blog Post: Elevating Your Podcast Guest Interview Game to Build Stronger Connections and to Achieve More

Would you like to maximize the impact of your podcast guest appearances? As someone who has spent eight years hosting and guesting on podcasts, I’ve discovered a simple trick that has completely transformed my experience as a guest, and I believe it can do the same for you. If you’re eager to make the most out of every podcast appearance, then this is for you.

I call it the “upside-down interview strategy,” and before I explain how it works and how you can implement it, let me share with you one of my worst interview experiences as a host.

Related: Using Quotes To Scale Up Your Podcasting Game

My Worst Podcast Interview

I was genuinely excited to have a prolific guest on my show. She was a renowned podcaster and a multi-time author with a reputable publishing house. Her work aligned perfectly with the theme of my show, so I couldn’t wait to have her as a guest.

My podcast focuses on personal transformation, and I was eager to delve into her own transformative journey and uncover some profound insights to share with the world. I had read her book and listened to her show, thoroughly preparing myself to create something truly exceptional.

However, as you might have guessed, she seemed unprepared. Instead of engaging in a dynamic and fresh conversation, it felt as if every question I asked her was redirected back to her rehearsed talking points. It was reminiscent of interviewing a seasoned politician, where answers become formulaic and predictable. We’ve all witnessed these types of interviews before.

She had become so accustomed to her media persona that she had become unapproachable. I consider myself a skilled interviewer with numerous interviews under my belt, but I simply couldn’t get through to her.

The experience I had on that particular podcast interview lacked any kind of spark and felt completely robotic. It wasn’t just boring for me, but also for the listeners.

People tune in to shows to gain fresh insights and, over time, they develop certain expectations and a sense of trust in the hosts.

Each show has its own unique culture, and as guests, we have the privilege of entering that tribe and sharing something meaningful with its members. Listeners grow to respect and love their host, who often serves as a representative for the audience. A good host understands this and asks the right questions to take their listeners on a captivating journey.

Therefore, listeners come to the show with the anticipation of such an experience. When a guest simply recites their talking points without engaging in a genuine conversation, it can be off-putting at best and downright insulting at worst.

Not only did I leave that episode feeling disappointed, but my listeners also felt let down. I share this story as a cautionary tale of how not to approach a podcast interview.

Now, I understand that some media professionals may argue otherwise. They might advise guests to stick to their talking points and redirect every question to their advantage.

However, I believe this approach contradicts the essence of podcasting today, and in doing so, we miss out on the true opportunities that guesting on a podcast can offer.

A Better Way To Look At Your Podcasts Interviews

Let’s think about each guest appearance as if it were a meal or a ceremony with a culture or tribe that you’re not familiar with. Picture yourself as the guest in this scenario. Your role is to observe and take cues from what’s happening to understand what to do and how to navigate the conversation, all while serving the host and the audience in the best possible way.

It’s important not to enter this special space and start talking endlessly about yourself or whatever you’re promoting.

Although I believe you already know this, it’s worth reiterating. Instead, approach it with genuine curiosity, active engagement, and a willingness to contribute. As a host, I can tell you that it’s a noticeable difference when guests exceed expectations. We’ve had conversations that went beyond our initial expectations, exploring unexpected and enjoyable topics.

And as listeners, we can all tell when something special happens in a conversation. We witness this phenomenon frequently in viral news segments featuring celebrities; it’s never the scripted pieces, but rather the unfiltered, authentic moments that resonate with us. That’s the kind of experience I’m inviting you to co-create with hosts today.

Unfortunately, as guests, we often become too focused on ourselves, our carefully crafted messages, and all the hard work we’ve put into our projects. We see this as our moment to share it all with the world.

However, I’m proposing a different approach—flipping the script, if you will—and it all stems from one simple idea: prioritize the show and the host above all else. This is what I like to call the upside-down interview.

The Benefits of The Upside-Down Interview Style

The Upside Down Interview Style has numerous benefits that set it apart from traditional interview approaches. I gave it this name because it flips the script and takes a different approach compared to what most guests typically do. Let me share some of the results I’ve observed, and I’d love to hear about the results you achieve when you start applying this method.

  1. The Upside Down strategy leads to better and more dynamic interviews. By adopting this approach, you venture into new territories and create a final product that is significantly enhanced. The conversations you co-create with the host become engaging and enjoyable for listeners, surpassing the impact of mere scripted talking points.
  2. This method turns the host into an enthusiastic fan. When you go above and beyond for the host, they become not just a supporter but an advocate for you. When someone helps me achieve my goals, I naturally want to reciprocate and assist them in reaching their own objectives.
  3. Leveraging hosts through the Upside Down approach allows you to expand your network. When hosts feel supported by your commitment and effort as a guest, they become eager to connect you with other hosts, partners, and potential advocates.
  4. This style enables you to forge stronger connections with the audience. Remember, the audience tunes in for a specific type of conversation. By collaborating closely with the host, you can co-create content that resonates with the audience even more than your standalone material would. By willingly exploring the topics and directions that the host wants to explore, you increase the likelihood of striking a chord with the host’s audience.
  5. The Upside Down approach leads to tangible outcomes such as increased sales, more leads, and higher book sales—whatever your specific goals may be.

So how do we do it? There are three steps.  Let’s dig into these one at a time.

#1 Understand the Host’s Goals

Understanding the goals of the host is the first step in becoming an exceptional podcast guest. It’s crucial for us, as guests, to grasp the amount of effort that goes into creating a podcast. From the recording time and editing costs to software and hosting expenses, there’s a lot involved.

Every podcaster, just like every guest, has a purpose behind what they do. To excel as a guest, you need to comprehend the host’s objectives and focus your appearance on serving their mission to the best of your ability.

Podcasts generate revenue through advertising, by helping listeners, or by assisting guests. Oftentimes, hosts combine these three approaches. The key lies in understanding what success means for the host and working towards achieving that success on their behalf. This means putting your content and agenda on the back burner and devoting your time and attention to creating something special for the host.

To uncover the host’s goals, there are a few important questions you can ask. Take note of these:

  1. Start by asking the host to share one of their favorite episodes and why it holds that distinction. This will provide valuable insights into the host’s preferences, the show’s culture, and the types of conversations they enjoy. Understanding their interview style and the topics they gravitate towards will go a long way in comprehending who they are as a host and what they bring to the table.
  2. Inquire about what qualities make a guest truly exceptional, and request specific examples. The more the host talks about their show and what they appreciate in guests, the better equipped you’ll be. These discussions will offer clues that you can piece together to form a comprehensive understanding.
  3. Most importantly, ask how the host monetizes the show or how it fits into their business. If you’re uncomfortable discussing money directly, inquire about their customer base and the services they offer. If they provide coaching or consulting, express interest in learning more about their framework and perspective.

#2 Frame Your Story Through Their Lens.

The next step in the upside-down interview approach is to frame your story through the lens of the host. It’s essential to understand the host’s goals and then shape your content and narrative accordingly. The goal here is to set the stage for the host to hit home runs while sharing your unique perspective.

An interview is like a dynamic improvisation, where there’s a constant back-and-forth exchange. In improv, one of the fundamental rules is to always say “yes and.” This means accepting what the other person presents and then building upon it in a fresh and creative way. The same principle applies to podcasting. When the host poses a question or provides an insight, take it, infuse it with your own insights and experiences, and then pass it back to the host.

Unfortunately, many guests overlook this aspect. Don’t be afraid to ask the host for their opinions and perspectives. Inquire about how they would respond in similar situations or what has worked for them in their own business or personal journeys. Hosts have a wealth of knowledge and experiences to share; all you need to do is ask.

So, let’s recap the steps we’ve covered so far in the upside-down interview approach. First, understand the host’s goals. This provides a foundation for the rest of the process. Second, frame your story through their lens, keeping their objectives and preferences in mind as you shape your content and responses.

#3 Compliment The Host

Now, let’s dive into the final step of the upside-down interview approach, which is simple but crucial: complimenting the host. Remember, the host represents the audience—they are the stand-in for the listeners.

By making the host look good, you’ll create a positive experience for the audience as well. Take the time to express how great their show is and compliment them on the intelligence of their audience for tuning in.

Treat this aspect as part of your job as a guest. Be genuine in your compliments, but if you can make the host feel good, you’ll undoubtedly bring smiles to the faces of the audience too.

The Upside-Down Interview Framework In Action

To illustrate, let me share an example from my recent appearance on the Happy Engineer Podcast with Zach White. It was an awesome podcast, and Zach proved to be an excellent interviewer and host. We had a truly enjoyable conversation. During our preparation, I discovered that Zach coaches engineers and that his show serves as a way for him to connect with potential clients, both among the guests and the audience—two of the strategies we discussed earlier.

During our pre-show discussions, I took the opportunity to ask Zach about his coaching principles and requested him to share some insights. He generously offered a few valuable perspectives, and then we delved into the interview.

By incorporating his specific framework into our conversation and looking at my journey and work through his lens, it turned into an engaging and dynamic discussion.

If I had solely focused on sharing my own framework and how I work with clients without considering Zach’s perspective, we wouldn’t have reached that level of connection and mutual learning.

The result was a truly enjoyable conversation where we both gained new insights. I’m confident that when the episode goes live, I’ll hear from his listeners because of the fantastic rapport we built during the show.

Once again, let’s recap the steps of the upside-down interview approach:

  1. Understand the host’s goals.
  2. Frame your story through their lens.
  3. Compliment the host and make them look good, enhancing the audience’s experience.

By following these steps, you’ll elevate your guest appearances, forge meaningful connections, and leave a lasting positive impression on both the host and the audience.

About Dan Cumberland

Dan Cumberland is on a mission to help bootstrapped entrepreneurs avoid burnout. Having hit the bottom before, he’s passionate about helping entrepreneurs get the insights they need to recalibrate their work/life balance so they have the energy and motivation to keep going. He is a 3x SaaS founder, serial entrepreneur, host of The Meaning Movement Podcast (, and a Product Strategist with the Venture Studio His work has been featured in Entrepreneur Magazine,, Fast Company, and more. His most recent project is a software for repurposing speech-based audio and video into viral-ready shorts: Outside of business, he’s a father, husband, avid reader, runner, health and fitness optimizer, and volunteer with the Carbon Almanac. He lives in Seattle with his wife and three kids.

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