If you want your story to connect, don’t think like a marketer. Think like Taylor Swift.

Recently, I faced one of the trickiest audiences in my speaking career—a room full of Girl Scouts, grades 6–12. Not my usual crowd of conference-goers and MBA students. The question: How do I make what I have to say matter to them?

Two words: Taylor Swift.

Taylor is many things—singer, songwriter, producer, performer, businesswoman, cat mom, cultural icon. But above all? She’s a master storyteller. And as you know, dear reader, story is what I do. And that’s exactly what I did at this event.

So, what can we learn about storytelling from Taylor Alison Swift? Here’s what I told the Girl Scouts—leveled back up for grown-ups like you.

For Leaders

Speak (Your Story) Now. Trust fuels leadership. But the higher we climb, the more we hide what actually connects us—our flaws. One of the first Taylor songs that hit me was the 10-minute version of All Too Well she performed on SNL. By the end, I was right there with her—and furious at Jake Gyllenhaal for stealing her scarf.  Vulnerability builds trust. Share your All Too Well moments.

It’s Me. Hi. I’m the Underdog. Good news: you don’t need to invent a main character. You are the story’s star. But make sure your audience roots for you—not the unrelatable superhero version. Think You Belong With Me, where Taylor watches the guy she likes date someone flashier: “She wears short skirts, I wear T-shirts…” The underdog wins hearts. Let them see the T-shirt version of you—that’s who they’ll want to follow.

I Remember It All Too Well—Because of the Details. Generic stories are forgettable. Specific stories stick. Taylor doesn’t say “our love was special.” She says it was like a “slamming screen door.” You hear it. You feel it. Add sensory details, brand names, nostalgia—make your story felt, not just told.

For Brands

Turn Singles Into Eras. Taylor’s songs don’t stand alone—they connect. Cardigan, August, and Betty tell the same story from different angles. Every album is its own era—a whole world. Brands should do the same. Don’t drop one-off campaigns. Build chapters that add up to something bigger—an era, a movement, a feeling. When your story evolves, your audience comes along.

Set the Stage with Story. The Eras Tour wasn’t just a concert—it was a story world. Each era had its chapter. Fans dressed the part. Friendship bracelets became tokens of belonging. Taylor handed her “22” fedora to one lucky fan, making them the star. Brands can do this too—creating experiences where customers don’t just buy, they belong.

Taylor shows that story isn’t just what you say—it’s how you make people feel part of something bigger.

Use This Story Strategy in Your Work

• Why Taylor? Because she may be the greatest mass-market storyteller of our time. She doesn’t just write songs—she rewrites the narrative. Again and again. For herself. For her fans.
• For leaders: Build trust with personal, detailed stories where you’re the underdog. Vulnerability connects. Relatability wins. Specifics make it stick.
• For brands: Don’t drop one-offs. Build eras. Connect campaigns. Shape experiences where your audience grows with you—not apart from you.
• EASTER EGG: Want to unlock your own Taylor-inspired story? Grab the Taylor Swift Storytelling Prompt Sheet I created for the Girl Scouts—perfect for team workshops, brainstorming, or just for fun. Download it now →
• Bring this Story Strategy to your team →

When you want to connect, embrace your Taylor era. Build trust. Bring people in.

Make every story part of something bigger.

 A version of this first appeared in Story Strategies—my monthly email newsletter designed to help you connect with your audience through the power of story. Get the next issue delivered to your inbox.