5 Leadership Lessons the Modern CEO Can Learn from Taylor Swift

Taylor Swift performing at one of her concerts

Source: Taylor Swift’s Instagram

Back in 2015, I took my wife Yvonne to a Taylor Swift concert for her birthday. For the Swifties out there, this was the 1989 World Tour. The concert was at Petco Park in San Diego. It was a huge concert, with over 45,000 fans in attendance. (I’m proud to say that I knew a number of Taylor Swift songs). At the time, I remember feeling amazed by the impact Taylor Swift had on her fans. As I watched thousands of people sing along to every word and wave their coordinating light-up bracelets in the air, I thought, “There is something to learn here.”

In the years since Yvonne and I went to that concert, Taylor’s fame has skyrocketed, and her fan base has exploded. She was named TIME’s “Person of the Year” in 2023. Even government leaders are paying attention. You’ve probably seen the statistics of the economic boost she brought to every city on the Eras Tour: $2.2 billion in ticket sales in North America alone, with an average of $13 million in U.S. ticket sales per show and 72,000 audience members per night (Source: Statista). Each Eras Tour concert-goer spent an estimated $1,300 on outfits, merchandise, dining and travel, boosting local economies by hundreds of millions of dollars in one weekend (Source: TIME).

Crowd at a Taylor Swift concert

Taylor Swift has a remarkable ability to connect with her fans. Despite the fact that she has millions of fans around the world, every individual feels like they have a personal connection to her. They feel like she’s their friend and understands what they’re going through.

Even my wife and I, who don’t consider ourselves Swifties, felt like Taylor was talking directly to us as she looked into the audience and told us how grateful she was that we were there; that we bought tickets and traveled to the concert and showed up.

So how does someone create a personal connection so strong with so many people? How has Taylor Swift created this movement that has real power and influence? This is something that many modern business leaders struggle to do.

Taylor Swift Eras Tour Poster

Source: TaylorSwift.com

Whether it is with employees or customers, trying to build a meaningful connection with so many is a significant leadership challenge, but one that Taylor has mastered. Here are 5 rules for leadership that business leaders can learn from Taylor Swift:

  1. Be ordinary. At the concert and in everything she does, Taylor demonstrates that she is ordinary. Her songs are an open book to her struggles. There is the obsession with her cats. While she is worth an estimated $1.1 billion, her fans still see her as someone who has the same life issues they have. She not only sings about what makes her life difficult, but she talks and posts on social media about it. The Swifties believe that she is like them.

  2. Talk about things that matter. Throughout her concerts, songs, and in all her messaging, Taylor Swift talks about life’s challenges that resonate with her fans. Whether it’s heartache, family issues, or the journey of self-discovery, she talks openly about her experiences. This vulnerability makes fans feel seen and empowered to face their own struggles head on. If Taylor can do it, then I can, too.

  3. Communicate openly. At the concert Yvonne and I went to, it was obvious from the start that Taylor was struggling with her singing. It was an amazing concert with great dancers and back-up singers, but you could tell that the main attraction was not at her best. She could have gotten through the concert without saying anything, but instead she told the audience that she had a cold and singing that night was hard for her. She then received one of the loudest cheers of the concert by asking her fans to help her sing the next song. Open and honest communication is often met with understanding and loyalty.

  4. Demonstrate that you care. The first time I became aware that Taylor Swift was different from other pop stars was when my wife showed me a YouTube video compilation of Swifties opening Christmas presents sent to them by Taylor Swift (it was called Swiftmas). She had studied fans’ social media to find their likes and activities, and sent them hand-wrapped, personalized gifts. She wrote them cards and even delivered one gift by hand. Taylor has also been known to go to pages like GoFundMe.com and donate the total amount needed. These well-publicized demonstrations of caring are one of the key ways that fans feel close to her. Every fan who watches those videos sees someone who is like them. Few things are as powerful as a leader demonstrating that they care.

  5. Be genuine. Taylor Swift built her brand from the ground up, and each fan feels that she is genuine. Appearing authentic and genuine as a leader is one of the most important attributes. During her concert, Taylor seems like she is having fun and living in the moment. Every album reflects what’s going on in her life. She is being who she is, and allows everyone to see that.

Taylor Swift with her Guitar at a concert

Source: Taylor Swift’s Instagram 

The final piece of the equation to make these learnings work is that you need to be good at what you do. Taylor Swift is an excellent songwriter and performer. If she did all the steps above, but was just average at her craft, she would not be what she is today. It is how she has leveraged her talent that has turned her into a global phenomenon.

When I look at this list, I have seen CEOs and business executives break each of these “Swift Rules” for leadership. When they do, it usually disconnects them with their audience. If you want to be the leader of a large organization with employees who follow you, then take a page out of Taylor’s book.


Pete Steinberg is an elite rugby coach, leadership consultant, and author. He can help you and your organization overcome challenges and achieve unparalleled success. Pete’s first book, Leadership Shock, will be published in April 2024. You can connect with Pete on LinkedIn and at PeteSteinberg.com.

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