Asking Emotionally Resonant Questions to Unearth the Why in Every Story

Storytelling in podcasting isn't just a conversation; it's a shared journey between host, guest, and listener, where everyone brings their own ‘why’ to the table. 

There’s something timeless about a good story. It pulls us in, not just because it entertains, but because it taps into something deeper—a need to understand, to connect, to see the world through someone else’s eyes.

What happens though when we start chipping away at the ‘why’? Why do certain stories matter to us? Why do we feel compelled to tell them? Why do we even care about the motivations and decisions that shape people’s lives? 

Ever have a child ask you "Why?" and then "But why?" - over and over like no answer is ever enough?  It's exhausting, to say the least. 

Maybe part of that exhaustion isn't just about explaining it in terms that the child will understand but it's that each why pushes us to dig deeper to find answers we hadn't considered ourselves, challenging us to gain a new level of self awareness.

In the same way, well-crafted questions for our guests aren't just about eliciting a response - they are about getting to the heart of their motivations, value and beliefs. This is where storytelling happens - where values and worldviews are unearthed and where connections are made. 

Emotionally Resonant Questions Have a Direct Impact on Your Show

1. Increase listener engagement: When guests share personal and relatable stories, listeners feel a stronger connection to the show, leading them to tune in more regularly and stay engaged throughout each episode.

2. Create episodes that resonate and get shared: Emotionally rich episodes leave a lasting impression, making listeners more likely to recommend and share your podcast with others.

3. Build trust and establish authenticity: Developing a reputation as a host who brings out genuine, heartfelt stories helps set your podcast apart, attracting listeners who value authenticity in content

Three Ways to Draw Out Meaningful, Emotionally Resonant Responses from Your Guests

1. Focus on pivotal moments: Ask about specific turning points or challenges that shaped the guest’s journey. These moments are often rich in emotion and reveal the guest's core values and motivations. For example, "Was there a specific moment when you realized this path was your calling? What was that like?”

2. Use layered questions: Start with a broad question, then follow up with more specific ones to peel back layers and encourage reflection. This helps your guest tap into underlying reasons and insights. For example, begin with “What led you to this choice?” and then you can follow up with, “How did that experience shape your perspective?”

3. Be comfortable with silence: After a guest answers, leave a brief pause rather than rushing to the next question. This silence often prompts guests to keep talking, leading to more thoughtful responses and deeper insights.

Thoughtful questioning reveals the essence of a story, turning an interview into an engaging, memorable experience - for the guest, the listener and the host.

In our most recent cohosted Podjunction episode with Steven Pemberton (part 2 of 4), he explored this art of storytelling in depth. Steven, a seasoned storyteller himself, shared how asking intentional, well-researched questions is not just about uncovering facts—it’s about creating a space where guests feel comfortable sharing their ‘why,’ and revealing what truly drives them.

So, if you haven’t already, check out the episode to hear more about his journey with storytelling, both as a guest and as a host. You’ll come away with fresh insights on how to bring more depth and connection to your own podcasting approach.

A personal note from me: This approach is just as much a learning journey for me as it is for the next person. When I asked Steven for feedback after our conversation, he graciously advised me to follow the natural flow of the conversation and, whenever I feel stumped, to keep digging by asking those “why” questions. It’s something I’m still honing as a host. So, if you’re working on this, too, know that we’re in this together!

As always, I’d love to hear from you! How are you connecting with with your guests to unearth their ‘why’? What’s working? What’s not working?

Reply to this email or let’s connect on Instagram | @iamsadafbeynon and LinkedIn | @sadafbeynon 

Cheers,
Sadaf Beynon
Host | Podjunction Podcast