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Mastering Storytelling: From Toasts to Interviews

image showing the various ingredients that go it storytelling
Discover essential tips for telling engaging stories, whether at weddings, interviews, or gatherings. Connect and inspire with your narrative.

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Why Storytelling Matters in Everyday Life

Storytelling is everywhere. It’s in the heartfelt wedding toast that makes everyone tear up, the compelling tale you share during a job interview to showcase your skills, or the funny anecdote you tell over dinner to make your friends laugh. Stories are how we connect. They make us feel understood, inspire hope, and build bridges between people. As Sarah Austin Jenness, executive producer of The Moth, says, Stories make us laugh, they make us feel hope, and they make us feel like it’s going to be OK.” So, what makes a story truly memorable? Let’s dive into the art and science of storytelling.

What Makes a Great Story?

  • Every story must have a clear beginning, middle, and end.
  • Tension and transformation are essential elements.
  • A strong emotional component captivates the audience.

A great story is more than just recounting an event. It has structure and depth. It’s the difference between saying, “I saw my ex at a coffee shop” and sharing how that moment made you feel, how it changed your perspective, and how you grew from the experience. Tension keeps the audience invested, and the transformation—how you or the situation changed—provides resolution. Without these elements, a story risks falling flat.

Choosing the Right Story

  • Focus on moments that have deeply impacted you.
  • Big decisions, embarrassing mistakes, and moments of vulnerability are fertile ground.
  • Use prompts to spark ideas, such as “What’s a moment I’ll never forget?”

With so many stories to choose from, it can be hard to know where to start. Think about the moments in your life that stuck with you. Maybe it’s a time you made a tough decision, faced a challenge, or learned an important lesson. Vulnerability often makes stories relatable, so don’t shy away from sharing mistakes or setbacks. Use prompts like “What’s something someone said to me that I’ll never forget?” to uncover those hidden gems.

Developing Your Story

  • Zoom in on the key details—where, when, and how the moment unfolded.
  • Boil the story down to one core message or takeaway.
  • Focus on the thoughts and emotions you experienced.

Once you’ve chosen your story, it’s time to develop it. Think of it as putting it under a magnifying glass. Where were you physically, mentally, and emotionally? What details will help your audience understand how this moment impacted you? Simplify your story into one sentence that captures its heart, like “I learned the importance of community after a disaster.” This will help you stay focused and decide which details to include.

Structuring Your Story

  • Start with action to grab attention.
  • Decide on a chronological, flashback, or other narrative structure.
  • Keep the flow smooth and logical for your audience.

A strong structure can make or break your story. Starting in the middle of the action immediately hooks your audience. From there, decide how you’ll tell the story—chronologically, through flashbacks, or starting with the ending and working backward. Whatever structure you choose, make sure the journey is easy to follow. The goal is to let your audience experience the story as you did.

The Power of the Ending

  • Show how you or the situation changed by the end.
  • Avoid tying everything up too neatly—real-life stories are rarely perfect.
  • Leave your audience with a sense of resolution or insight.

Endings are crucial, but they’re not always easy to write. The key is to show transformation. How are you different now than you were at the beginning of the story? Maybe you gained a new perspective, learned something about yourself, or simply found closure. While it’s tempting to wrap everything up with a neat bow, real-life stories often end imperfectly, and that’s OK. Authenticity is more important than perfection.

Knowing When (and When Not) to Share

  • Assess your emotional readiness, especially for vulnerable or traumatic stories.
  • If you’re stuck on one scene, it might be too soon to tell the story.
  • Wait until you’ve processed the experience enough to find its meaning.

Not every story is ready to be told. If you’re reliving a traumatic event every time you think about it, or if you’re still unsure of the story’s ending, it might be best to press pause. Give yourself time to heal and process before sharing. Your well-being comes first, and there’s no rush to tell a story before you’re ready.

Practice Makes (Almost) Perfect

  • Practice your story until you’re comfortable, but don’t memorize it word-for-word.
  • Focus on the opening and closing lines to anchor your delivery.
  • Use bullet points or mental cues to guide you through the story.

Even the best storytellers get nervous, but preparation can help. Practice your story until you know it well, but avoid memorizing it word-for-word. A memorized story can sound robotic, and if you forget a line, you risk freezing. Instead, focus on nailing the opening and closing lines, and use bullet points to keep yourself on track. If you get stuck, just ask yourself, “What happened next?”

Storytelling as a Tool for Connection

  • Engage your audience by keeping the story concise and interactive.
  • Encourage others to share their own stories in response.
  • Remember, storytelling is about building connections, not stealing the spotlight.

At its core, storytelling isn’t about you—it’s about connection. Whether you’re giving a wedding toast or chatting with friends, keep your story short and engaging. Leave room for others to share their stories, too. A great story is a conversation starter, not a monologue. By focusing on connection, you’ll ensure your story resonates long after it’s told.

Conclusion

Storytelling is a powerful skill that can transform how we connect with one another. From selecting the right story to practicing its delivery, each step of the process helps us share our experiences in a way that resonates. Remember to focus on structure, emotional depth, and transformation, and don’t forget to let your story breathe with natural authenticity. Whether you’re giving a wedding toast, acing a job interview, or simply sharing a laugh with friends, storytelling is your gateway to creating meaningful connections. So, what’s your next story going to be? Start crafting it today!

If you want more information on telling great stories check out our book “How To Hack Humans” on Amazon. Also available in audiobook format. 😉

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