Leadership lessons from the iconic Taylor Swift

I’m fascinated by changemakers and cause-based leaders who are doing good for the world. And if you follow me on Instagram or TikTok, you’ll probably notice that I am often interested in unlikely changemakers — those who didn’t necessarily seek leadership positions — but who are still making positive change often in ways they didn’t initially set out to. I spend a lot of time reflecting on what makes them compelling and what impact they’re having. Today, I want to take a moment to highlight Taylor Swift, not for her musical talent, but for her role as a CEO of her business and as a leader in cultural shifts – both of which often go unnoticed.

First let me tell you a bit about my own exposure to Taylor Swift. I have two teenage daughters (that should be enough to give you an idea), but in 2021 my eldest daughter, according to Spotify, listened to Taylor Swift more than almost anyone else in Canada – she was in the top 0.0001% of listeners!! Her hours of listening totaled 150 days! Think about how much listening time that actually is. (This was during a remote-school-from-home year and Taylor was our household soundtrack). That’s when I started paying more attention to Taylor.

There’s no denying Taylor’s musical success: it only takes a minute to google her very long list of record-breaking stats, accolades and awards. Her ability to reinvent herself musically and artistically speaks volumes about her visionary mindset and ability to remain both relevant and impactful. She also reflects the human condition in her music in a way that connects with her fans and their experiences. This is essential for any changemaker even if selling emotions isn’t your specific business. Connecting with the emotions of your audiences and tapping into something they care deeply about is much more impactful than simply stating facts about your cause.

I’ve also enjoyed exploring Taylor’s growth over the years as she has become much more self-aware (a hugely important and often overlooked leadership trait) and confident in her own voice and what she cares about. And while Taylor is at the top of her game right now, she has faced incredible backlash and patronizing belittling over the years for daring to be young and female and successful; I read an article by Kimberly Cortez who examined the level of hate she has received and attributed it to internalized misogyny (in all of us) and sexism particularly within the entertainment industry and media and I would agree. What I’ve loved in recent years is seeing Taylor find and use her voice and platform to speak up and call out gender biases and double standards — which is not always easy to do when it’s directed at you. Changemakers become the voice of something and that is something she has become very good at.

That all being said, I’m currently fascinated by Taylor as a CEO. She has consistently demonstrated her acumen as a businesswoman. From managing her brand to making strategic decisions about her music catalog, she has showcased the foresight and determination expected of a top-tier CEO. Her recent Eras Tour concert movie made a deal directly with AMC Theatre rather than channeled through traditional movie studios (Beyoncé did the same with her upcoming Renaissance Tour concert movie) which also benefits small and local movie theatres. There has also been much said the Taylor Swift Effect — Taylor’s direct and measurable impact on the economy. A well-cited study by Question Pro calculated the direct impact on host cities (and their local businesses) from her Eras Tour was around $5 billion. Estimates are that the total economic impact likely exceeded $10 billion. This is impact on the overall economy not her own pocketbook. And that’s just for her 5 month tour.

Taylor’s leadership extends beyond the boardroom and the stage. Her philanthropic efforts and advocacy for various causes are inspiring. She is known for donating millions of dollars to a myriad of charities, ranging from hurricane relief funds to funding music departments at six US colleges. As a promoter of children’s literacy, Taylor has generously donated money and books to various schools across the country, aiming to enhance education. She’s known to give back to the communities she visits on tour, donating to local Food Banks along the way. It’s hard to know how much she’s given but it appears to be significant – estimates are in the hundreds of thousands of meals in each location. Of course she has the money to do so, but how many other CEOs and multi-millionaires or billionaires can point to the same generosity?

But what sets her apart even more is her approach to her team’s well-being. This is where her progressive CEO vibes really kick in. For one, she offers benefits that are less common in that industry such as insurance for her dancers. And she gives bonuses to her employees and subcontractors – and even though this is done sometimes by others, it’s the amount she’s been giving that’s noteworthy. In the Eras Tour so-far, it’s estimated she’s given a total of US$55 million to hundreds of her staff including road crew, caterers, dancers and truckers. I’d love to see a comparison to many Fortune 500 CEOs and how their bonuses are distributed at all levels in their organizations.

I’m not telling you all this to try to convince you to be a Taylor Swift fan; she certainly doesn’t need my help in that. I am using her as a demonstration that change-making comes in all forms. We can all challenge the norms of our industries (whether that’s related to fair compensation, calling out harmful assumptions or discrimination, or daring to do things differently than how they’ve been done in the past). We can all use the platforms we do have to inspire others and create a better future. And we can all lead with kindness and uplift others — these are true guides for humanity.

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