No Job Too Small: Jamming with Taylor Swift

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.

Taylor 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 Taylor on stage during the middle of her set, and together they would sing a song from the guest’s catalogue. 

The idea would allow Taylor 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. Taylor’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 Taylor work behind the scenes would exemplify a lesson in business leadership that has stuck with me to this day.

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 Taylor, 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.

Taylor 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. Taylor’s famous personal touch in the flesh.

As we stepped into the arena for soundcheck with her band, my colleague Chris and I stood beside her father, Scott, watching on. While Taylor led the band through "Closer" and consulted with Tegan and Sara on creative decisions, he was equally welcoming and regaled us with facts and figures from the tour. Over 100 crew members, 24 trucks, 15 buses, and 86 shows across 12 countries. Every key decision was made by Taylor, who was no different than the CEO of a successful multinational business. 

This was not a pop star who let other people pull the strings, this was a leader involved in all elements of her business, top to bottom. Much like Tegan and Sara, we were proud to tell her father.

Later that night, as we watched the three of them on stage successfully surprising and delighting 20,000 delirious fans, I kept recalling a business mantra that I knew all too well as a talent manager: no job too big, no job too small. That day Taylor was the perfect embodiment of its folksy wisdom. 

The successful leader is someone equipped to make a big strategic impact at one moment and be in the trenches on a customer relationship issue the next. Taylor had conceived the surprise guest strategy on a tour that would go on to sell 1.7 million tickets and gross US$150 million. She also found the time to make homemade jam to create a quiet but indelible relationship memory behind the fanfare.

Was making that jam a good use of her time that week? It turns out, yes. Besides being a relaxing ritual amidst her high-pressure life, it was a disarming gesture from a global superstar that quietly levelled the playing field. The potential stress of the day dissolved into a shared confidence that everyone was in it together. I started to see the homemade jam as a subtle and unconventional type of leadership through personal connection and service.

We often ask ourselves how effectively we’re using our time, and good leaders are great at knowing what to do, when. If your calendar has a blank space, what’s the right mix of big and small tasks? When you’re always working on esoteric strategy and ignoring small operational glitches, you may have an issue. If you’re always in the weeds and not tackling the future, ditto. 

So perhaps we should take a cue from Taylor Swift and start with a very basic premise. Every week do something small but personally meaningful, and every week do something big and challenging. Just like we saw her do that day on the Red Tour. As a metaphor for Taylor’s leadership style, the big job of jamming with her band to a packed arena seemed no more important than the small job of making homemade jam to welcome her guests and put them at ease.

That’s a lasting lesson I’ve never been able to shake off.

This essay originally appeared in Douglas Magazine.