Steve Harper and storytelling coach, Michelle Cutler, discuss the importance of storytelling in communication, emphasizing the need to fine-tune one’s voice and approach. They highlight the value of brainstorming without a specific goal to foster creativity and the use of prompts to generate ideas. Michelle shares her experience with publishing micro-memoirs on Substack, using themes like truth and regret as thematic generative prompts. They also explore the significance of practicing storytelling, whether through writing, voice recordings, or impromptu sessions. Michelle outlines her coaching process, which includes tailored questionnaires, strategy sessions, and actionable follow-ups. She stresses the importance of making stories impactful and memorable, aiming to leave a lasting impression on the audience. Connect with Michelle through her website for storytelling coaching services.
Storytelling is an art that captivates and connects us all, whether it’s in a casual conversation, a formal presentation, or a creative project. However, mastering it can be tricky. Steve Harper and Michelle Cutler, two storytelling professionals, recently discussed how to overcome the challenges of storytelling and refine the skill through practice, preparation, and reflection.
Their insights, shared during a candid podcast conversation, offer practical tips for overcoming the fear of the blank page, crafting compelling narratives, and adding humor through relatable confusion stories. Read on to learn how you can apply these ideas to enhance your own storytelling abilities.
For many, staring at a blank page can be daunting. How do you start? What if you don’t have anything interesting to say? Michelle suggests a few strategies that can help ease this anxiety:
“Practicing makes a difference,” she says, “whether you’re bouncing it off somebody else, recording yourself, or writing it down. Find a method that works for you.”
One of her favorite techniques is using a voice recorder. It’s ideal for brainstorming and capturing thoughts without the pressure of perfecting them. “When I’m generating ideas, I just free flow into the voice recorder. Then, I transcribe it and search for keywords,” she explains. Once transcribed, Michelle suggests organizing these snippets into a “personal database” of themes, ideas, and story components.
Having a ready reference like this eliminates the fear of the blank page. Instead of starting from scratch every time, you can review your stored ideas and build on them, making storytelling feel less like a daunting task and more like a creative puzzle.
Some of the best stories arise from confusion, misunderstandings, or awkward situations. Why? Because they’re relatable, unexpected, and, when told right, they can be hilarious.
Steve shared his own memorable confusion story from his radio career. He was thrilled to interview Rod Stewart over the phone and kicked off the conversation confidently:
“Hey, Rod, how’s it going? How’s everything with you? Oh, fantastic! How’s Kelly doing?” Silence. Then: click. The line went dead.
It wasn’t until after the call that Steve realized he’d made a huge mistake: he had mentioned Stewart’s ex-wife, Kelly, whom the singer was embroiled in a legal battle with at the time. His 38-second interview became a classic example of how excitement and nerves can lead to confusion—and a great story.
We’ve all been there, caught in a moment of awkwardness or mistaken identity. These incidents, while embarrassing in the moment, can become the basis for stories that audiences love because they reveal our shared humanity and vulnerability.
For those looking to refine their storytelling skills, Michelle’s approach to coaching is both methodical and creative. Every session is tailored to the individual and their specific goals. Here’s a peek into what a typical coaching experience looks like:
Michelle starts by asking a series of questions through a detailed questionnaire. This helps her understand what the client wants to achieve and the nuances of their story.
Based on the questionnaire, Michelle prepares extensively for the strategy session, bringing specific questions and exploring the unique aspects of the client’s project. This hour-long call is designed to identify obstacles, clarify the narrative, and find the best format for the story—whether it’s an essay, a screenplay, or a chapter in a larger work.
After the session, Michelle provides what she calls “Golden Notes”—a concise, actionable plan that includes follow-up steps, suggested outlets, and detailed feedback. Instead of just a recording of the conversation, clients receive structured notes that make it easy to implement what was discussed.
If the project is long-term, Michelle continues to check in, offering additional development sessions and real-time guidance as the story evolves.
Whether you’re writing a screenplay, a book, or even crafting a speech, the goal should always be to leave a lasting impact. Michelle draws on her experience in film and screenwriting to highlight the importance of a strong ending:
“When the lights go down, what’s the first thing the audience sees? And when the credits roll, what are they taking away?” she asks. Creating a powerful beginning and a meaningful ending ensures that your story resonates long after it’s finished.
Everyone’s takeaways will be different, but the objective is to make sure they walk away feeling something—be it laughter, inspiration, or a new perspective.
Michelle and Steve agree that developing a storytelling routine is essential. Here are a few tips to help you build yours:
• Record Your Thoughts: Use a voice recorder to capture spontaneous ideas. Don’t worry about being polished—this is about getting the raw material down.
• Create a Keyword System: Transcribe your recordings and look for recurring themes or keywords. Create a document where you can easily search and reference these ideas.
• Experiment with Formats: Is your story best told as an essay, a podcast, or a speech? Don’t be afraid to try different formats until you find the one that feels right.
• Get Feedback: Share your stories with a friend or coach to see how they land. Sometimes, what’s clear in our heads can come across differently to others.
Final Thoughts
Storytelling is a skill that takes time and practice to develop, but the rewards are immense. By organizing your ideas, embracing your moments of confusion, and using structured support when needed, you can transform everyday experiences into engaging stories that captivate your audience.
Ready to take your storytelling to the next level? Check out Michelle’s website to learn more about her coaching services, read her latest projects, or explore her library of storytelling prompts and resources.