Creating Conversations People Actually Remember
- Jun 7
- 3 min read
By Jason Sherman
When I started my podcast, Strap On Your Boots, I thought the key to a good interview was keeping the energy high and making every answer sound impressive. Over time, I realized the conversations people connected with most usually happened when guests stopped trying to sound polished and started talking honestly about difficult moments they experienced while building their businesses and careers.
A lot of business podcasts focus heavily on outcomes. They focus on the success story after everything worked out. What I became more interested in was the process behind those outcomes.
I wanted to understand how people handled uncertainty, how they recovered from mistakes, how they pushed through setbacks, and how they solved problems when there was no obvious answer in front of them.
That changed the kinds of questions I started asking during interviews. Instead of only asking guests what worked, I started asking about what failed, what almost broke the business, what they misunderstood early on, or what they would do differently now. Those were usually the moments where the conversation became more real and relatable for listeners.
I remember interviewing founders who openly talked about burnout, financial pressure, bad hires, and periods where they genuinely did not know if things were going to survive. Those moments usually created the strongest response from listeners because people recognized themselves in those experiences. One guest explained how they spent months following advice from the wrong people before realizing they had completely lost focus on why they started the business in the first place. Another talked honestly about wanting to give up after hitting a wall financially and emotionally. Those conversations stayed with listeners because they reflected the parts of entrepreneurship people rarely talk about publicly.
I’ve also tried to be honest about my own experiences during episodes. While working on my various documentaries and building technology platforms over the years, I found myself making sacrifices socially and mentally that a lot of people around me did not fully understand at the time. There were long stretches where I stayed focused almost entirely on the work, constantly thinking about editing, interviews, production, and finishing the project. Talking about those experiences openly on the podcast helped me realize listeners connect strongly with honesty, especially when conversations move beyond polished success stories and into the reality of uncertainty, exhaustion, persistence, and growth.
Over time, I also figured out a format that worked well for my audience. Most episodes of Strap On Your Boots are around fifteen minutes long. I found that shorter conversational episodes kept the discussions focused and practical. I want listeners to walk away from every episode with something useful they can immediately apply to their own business or career. Sometimes that comes from a strategy someone shares. Other times it comes from hearing how somebody navigated a difficult situation or changed their thinking after making a mistake.
Building long-term trust with an audience takes consistency and honesty. I think listeners can tell very quickly when a conversation feels overly rehearsed or carefully managed. People connect more deeply when guests are willing to lower their guard a little and talk openly about uncertainty, fear, or failure alongside success.
I try to do the same thing myself during conversations. Some of the most important lessons I’ve learned professionally came from situations that did not go according to plan. Sharing those experiences creates a more honest relationship with listeners because it reminds people that growth usually happens through trial, error, adaptation, and persistence over time.
Podcasting has also taught me that meaningful conversations often happen unexpectedly. Sometimes a guest starts the interview giving prepared answers, but eventually something shifts and the discussion becomes more personal and reflective. Those moments usually stay with listeners long after the episode ends because they feel genuine.
Over the years, I’ve spoken with startup founders, CEOs, creatives, consultants, technologists, and even astronauts, and I’ve noticed that the most memorable conversations usually circle back to the same themes: uncertainty, resilience, sacrifice, curiosity, and learning how to keep moving forward when things become difficult.
At the end of the day, I think audiences stay engaged when they feel like they are listening to a real conversation between people trying to understand challenges, growth, and experience together. That sense of honesty and curiosity is what continues to keep me interested in podcasting, and I think listeners can feel it too.
Connect With Jason
Comments