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Taylor Swift’s Masterclass: Lessons in Leadership for Schools

Posted in Change, SD45, tagged educational leadership, Eras Tour, leadership, music, Taylor Swift, Vancouver on December 10, 2024| 2 Comments »

When the 2-minute countdown clock appeared on the jumbotron, the crowd was already in a frenzy. Our bracelets, which would soon flash in unison, hadn’t even activated yet. A 3+ hour phenomenon ensued—a concert that was part live music, part immersive storytelling.

This past weekend I joined more than 150,000 “Swifties” for the final 3 nights of The Eras Tour in Vancouver. While I felt like one of the few in the crowd who didn’t know the words to all the songs, nor did I have any bracelets to trade, I was taken by the amazing event that is a Taylor Swift concert—like nothing I had ever seen. Swift isn’t just an artist—she’s a master of connection, reinvention, and community building.

So, like any educator in the crowd who never truly clocks out, I was left wondering: What can teachers and leaders learn from her? What lessons do her concerts hold for us?

Reinventing Relevance

Taylor Swift has transitioned seamlessly from country music to pop and now to genres blending indie, rock, and even cinematic storytelling. She evolves not just to stay relevant but to stay true to where she is in life. In schools, reinvention isn’t just important, it is essential. The world is changing rapidly—students’ needs, societal expectations, and technology are all evolving. Like Swift, we need to find ways to stay relevant while staying true to our core values. Embracing change doesn’t mean abandoning the past—it means using it as a foundation to innovate and stay relevant.

Storytelling That Sticks

Swift’s songs resonate deeply with fans because they tell authentic, relatable stories. Her music isn’t just entertainment; it’s a connection. At the concert, the crowd became a single voice, shouting every lyric in unison – quite the testament to the power of a shared experience. In schools, our stories—both as educators and as a community—matter. One of the greatest powers of schools lies in the human connections we make with colleagues and students. Sharing the successes, challenges, and dreams of our schools can build trust and engagement with students, parents, and staff. Schools are at their best when they transcend the transactional and become spaces of genuine connection and shared purpose.

Building Belonging

When you look at Taylor Swift’s fans, the “Swifties,” you see more than just an audience—you see a community. Swift has created a space where every fan feels seen and valued. Schools can learn from this by building strong communities where students, staff, and families feel part of something bigger. Whether through shared values, celebrations, or collaborative projects, the power of belonging cannot be underestimated. Swift’s concert was a celebration of community, like all our events in schools where we come together face-to-face. For example, our high schools hold Grade 8 retreats each fall to make students feel they are part of their new school community – mirroring Swift’s ability to foster inclusion.

The Power of Details

If you’ve ever attended a Taylor Swift concert, you know the level of detail she brings to every performance—from the stage design to the secret songs in her setlist. Everyone was buzzing in Vancouver about what the secret songs would be the night we were there and they are a great example of both the personalization and commitment to every single detail. The 3 hours are tightly scripted but also made to feel completely real and authentic. These details create a memorable experience. In schools, details matter too. Whether it’s a well-planned field trip, thoughtful lesson design, or personalized feedback for a student, the little things add up to make a big impact. I recently visited a science class with a masterfully designed experiment. The students were completely engaged, and the real effort had been in the careful setup, not just the execution.

Lifelong Learning in Action

Swift’s career is a testament to growth. She’s learned from challenges, such as disputes over her music rights, and she’s used those lessons to become stronger. She was great when I saw her concert in 2015, but she is completely different today—an ongoing reinvention. Schools are the epicentre of lifelong learning. We teach students that growth isn’t just for the classroom—it’s for life. As educators, modeling this growth mindset in our work is essential. Using the Swift analogy of growth in the 9 years between her concerts in Vancouver in 2015 and 2024, schools could have been great in 2015. But if they haven’t changed in the last nine years, they may still be fine, but it’s a missed opportunity to evolve as the world has changed.

Leading with Influence

Swift isn’t just an artist; she’s a leader in her industry, using her platform to advocate for change and inspire her fans. Similarly, those of us in schools have the opportunity to influence our communities in positive ways. By setting an example, standing up for what matters, and leading with conviction, we can inspire students and staff to strive for their best. Teachers are the adults children spend the most time with after their immediate family, and this is an amazing opportunity to lead and inspire.

Empathy Is Everything

What sets Swift apart is her ability to make fans feel like she truly understands them. She is known for choosing the empathetic path, whether through small gestures at concerts or interactions with fans and this resonates with her supporters. The crowd in Vancouver was the nicest I have ever been part of – a testament to the culture of kindness Swift fosters. This empathy is something schools should all embrace. Whether it’s understanding a struggling student’s needs or supporting a staff member, empathy builds trust, encourages resilience, and strengthens relationships.

Participation Breeds Engagement

Swift engages with her fans in ways that make them feel involved, from dropping Easter eggs in her social media posts to acknowledging fan-made bracelets. Schools can do the same by amplifying student voice and encouraging participation. When students feel heard and seen, they become active participants in their education, not just passive recipients.

Final Thoughts

Taylor Swift’s concert was more than a spectacle—it was a masterclass in connection, relevance, and leadership. As educators, we can draw inspiration from her ability to engage and uplift, to adapt and evolve, and to create a sense of belonging for everyone she touches.

Perhaps the biggest takeaway is this: in both music and education, it’s not just about what we deliver—it’s about how we make people feel. Swift understands this instinctively, and it’s a lesson we need to live everyday in our schools.

When we approach our schools with Taylor Swift’s energy, heart, and attention to connection, we create not just learning spaces, but thriving communities where everyone feels they belong. Because, like a Taylor Swift concert, schools should leave everyone feeling they were part of something extraordinary.

I have previously written about other musicians connecting them to education including Paul Simon and The Tragically Hip.

I used both Chat GPT 4 and Claude to give me feedback on various drafts of this post.

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Some Hip Advice

Posted in Change, Professional Development, tagged music, Terry Fox, Tragically Hip on August 31, 2016| 9 Comments »

It was a uniquely Canadian event. More than one-third of our country gathered in front of screens across Canada on Saturday, August 20th to watch The Tragically Hip perform their final concert in Kingston, Ontario. In mid-July I joined a hockey arena full of fans for an event, as they began their tour across Canada, that was far more than just a band playing a concert. For my non-Canadian readers, it is hard to fully give context to the tour and the culminating concert, here is one of many tweets from the final night that attempted to share some perspective:

Of course dozens of newspaper columnists, bloggers and others have tried to give some context to what has happened this summer. Whether it is drawing connections to Terry Fox, or the power of our uniquely Canadian identity, much has been said.

I tend to see events like this differently, through my education window. So, in the afterglow of the summer the Tragically Hip engaged the country, just what are my takeaways, lessons and reminders for our schools and learning. Some good ones, I think, as we start a new year.

We love to gather as a community. While the final concert was broadcast on television, radio and across the internet, people tended to gather together to watch it rather than on their own. Whether it was at community centres, parks, or neighbourhood parties, people wanted to have the shared experience of watching the concert together. Just as while learning can more and more be something done online and alone, the great power of school is that they are gathering places in our community.

Canadian History is Cool and Worth Learning. As a Social Studies teacher, of course I am a little biased. I have always thought this. I often find that students struggle to see Canadian history with the same “cool” factor as US or European history. And those of us who have taught Canadian history may be somewhat to blame. The Tragically Hip regularly sing about Canada and its history with songs like Nautical Disaster (war) to Wheat Kings (crime and punishment) to Fireworks (hockey and the Cold War). Fans probably did not realize they were getting regular history lessons. You can find the stories behind all the Hip songs on A Museum After Dark: The Myth and Mystery of the Tragically Hip.

We have an obligation to be sure our children learn the history of First Nations people in Canada we didn’t learn in school. Lead singer Gord Downie spoke directly to Prime Minister Justin Trudeau during the final concert saying:

We’re in good hands, folks, real good hands. He cares about the people way up North, that we were trained our entire lives to ignore, trained our entire lives to hear not a word of what’s going on up there. And what’s going on up there ain’t good. It’s maybe worse than it’s ever been, so it’s not on the improve. (But) we’re going to get it fixed and we got the guy to do it, to start, to help.

This work we take exceptionally seriously in our schools. Even within the last five years there have been massive changes to the way we work with local First Nations and how we teach history in schools. Many of us are invested in the work that has come from the Truth and Reconciliation Commission and continuing to move this forward. So Downie’s challenge to the Prime Minister is the same challenge that we are taking on in schools.

Music connects people. There is an amazing power of music to bring people together. It was interesting to see the concert on right in the middle of the final weekend of the Summer Olympics. If there are two things that connect people together across geography, culture and language like no other, I think they are music and athletics. This video from the CBC nicely ties together the Olympics and the Tragically Hip. And again, it is just a nice reminder for us in schools that yes reading, writing, math and a host of other academic pursuits matter, but so does music. Music brings communities together and we need music in schools to help connect us.

No dress rehearsal. There are a lot of lyrics one can take from the Tragically Hip to reinforce life lessons. The final song they played at their Kingston concert was Ahead by a Century. And to borrow from the song “No dress rehearsal, this is our life”. Of course given Downie’s medical diagnosis, it was particularly powerful. And again for schools a reminder that grade 1 is not a preparation for grade 2, and grade 7 is not a preparation for high school, nor is high school a preparation for university. Grade 1 is grade 1. We need not live in a continual state of dress rehearsal.

Uniquely Canadian. In our house the final concert opened up a great conversation about the CBC. Why do we have it? Why didn’t they play any commercials? Who owns it? Does the United States have something like the CBC? It was a reminder of some uniquely Canadian institutions that we need to explain, and understand if we want them to be preserved. And of course that was just one example. The online response from inside and outside Canada was that the “event” was something that would unlikely happen elsewhere – which opens up a series of good questions about what is unique about Canada and being Canadian.

I am far from an expert on the Tragically Hip. Including the show in Vancouver, I have now seen them perform live once. I did love to be part of something bigger than me. It is something I think we all thirst for – and something we try to do in schools each day, for us and for our students. The Hip and their tour across Canada helped remind me of some of the core principles of what we are trying to do in school.