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We often think that great leadership requires big spectacle and high stakes, but sometimes it arrives in the smallest details. In 2013, while managing Tegan and Sara, I witnessed an unassuming masterclass from one of the world’s biggest stars in a quiet dressing room backstage.

Earlier that year, my inbox had lit up with an email I never expected in my wildest dreams: “Robert Allen here. I am writing to extend a personal invitation from Taylor for Tegan and Sara to join her onstage.” I stopped in my tracks and took stock of the moment. This was no ordinary Taylor. This was Taylor Swift.

Providing Opportunity

Swift was in her Red Tour era, and her longtime management colleague Robert Allen was helping to organize a unique show concept she had conceived. Select tour stops would feature a surprise guest with a twist — rather than appearing as a conventional opener, the surprise guest would join Swift on stage during the middle of her set, and together they would sing a song from the guest’s catalogue.

The idea would allow Swift to shine a spotlight on artists and songs she loved, creating mutually reinforcing viral moments. Some shows included a legend like Jennifer Lopez or Carly Simon, other shows featured a rising star. The anticipation became part of the rhythm of the Red Tour, rewarding superfans and transforming a global arena run into a different story each night.

We worked quickly to confirm Tegan and Sara as the surprise guest for an upcoming tour stop at The Staples Center in Los Angeles. Plans were put in motion to sing together on “Closer,” the biggest pop single of Tegan and Sara’s career at the time. Swift’s band would learn the song, and all Tegan and Sara had to do was be ready to sing it with her in front of 20,000 screaming fans. No pressure.

When we landed in L.A. a few months later, I knew we were ready for a big moment in Tegan and Sara’s career. What I didn’t know was that watching Swift work behind the scenes would exemplify a lesson in business leadership that has stuck with me to this day.

Big Venue, Small Touches

Walking through private corridors at The Staples Center upon arrival, we passed the fabled dressing rooms of the NBA’s Lakers and the NHL’s Kings and gazed at championship photographs. As we got situated in our more modest dressing room a few doors down, we glanced at the hospitality rider on a draped table in the corner and noticed something unexpected. Standing beside the standard items — water, wine and snacks — were four Mason jars of strawberry jam and a carefully placed handwritten note from Swift, welcoming Tegan and Sara to the tour.

None of us could believe she had taken the time to personally write a welcome note, but when she sauntered into the room a few minutes later to say hi, we were even more dumbfounded.

“Did you see the jam I made for you?” she excitedly asked Tegan and Sara.

Swift was famous for her ability to create personal connection with her fans, but personally making jam for Tegan and Sara? How could someone who juggled constant media obligations, millions of fans and a relentless touring schedule find the time?

Without missing a beat, she explained that with L.A. being a four-night stand, she was stationary and wanted to unwind at home by making batches of homemade jam. We were the lucky recipients of her ritual, and it was one of the most memorable welcomes we had ever received. Swift’s famous personal touch in the flesh.

so many responses of “its nice that you’re privileged enough to be able to steal from Target willy nilly!” and that’s not at all what this is about. like, yeah, shoplifting and loitering and graffiti and breaking the rules is, obviously, part of “do crime”. but they’re not parts you have to do.

would you help someone get an abortion where it was illegal?

would you help a trans friend get healthcare that had been criminalized?

would you shelter someone fleeing persecution, even if the law said not to?

would you help a gay couple stay together when the state decided their relationship was unlawful?

instead, would you report someone else for breaking the law? will you snitch on your hungry neighbors for stealing food? on your homeless neighbors for sleeping where they’re able?

+ bonus: Willem Dafoe jumpscare