What Taylor Swift can teach leaders about reinvention and trust

It’s not often you see Taylor Swift and Harvard Business Review in the same sentence. But for Kevin Evers, Senior Editor at HBR and author of There’s Nothing Like This:The Strategic Genius of Taylor Swift, the connection couldn’t be clearer.

Swift, he says, is one of the most strategic thinkers in business today. Not just because she’s successful but because of how she’s done it.

“When I sat down to write this book,” Evers tells me on the Work’s Not Working… Let’s Fix It  podcast, “I didn’t approach her any differently than I would a great founder like Steve Jobs or Jeff Bezos. Taylor is operating in a very tough industry. And she has somehow found a way to stay relevant and to grow her popularity two decades. You don't grow to this level of success and popularity without having great entrepreneurial instincts. She's evolved and adapted as the industry swirled around her.”

So what can people leaders actually learn from a global pop star?

Reinvention with backbone

Let’s start with the most famous move in modern music: the re-recording of Swift’s first six albums. After losing ownership of her master recordings Swift didn’t take the hit. She built a workaround. Four albums in the Taylor’s Version releases have outsold the originals and devalued the private equity firm’s purchase.

“She had no leverage,” Evers says, “even though she was a huge superstar. There's really nothing she could do because she signed a contract when she was 15 years old.”

So she invented leverage. She re-recorded the catalogue and made it a fan movement. And now she owns it all. That’s creativity. That’s curiosity. And that’s strategy.

In the world of work, where many still feel disempowered and undervalued, the lesson is that we can’t always change the structures but we can change our response.

What’s just as important is the clarity Swift brings to her decisions. “Taylor reinvents herself,” Evers adds. “But the core of what she does never changes. And she has such a deep understanding of what she's really great at and what her fans want from her.”

Too many organisations pivot without focus. Swift shows what it looks like to change with purpose, not panic.

Trust drives change

What’s striking is that Swift can reinvent without losing loyalty. She’s changed genres, aesthetic, tone and business model. But her audience has stayed with her. She’s genre-hopping but always consistent. “Taylor understands that her fans want more than music from her. They want intimacy, they want connection, and they want vulnerability. So even though Taylor is moving through these genres she's not changing those core sensibilities.”

That connection – call it trust, call it intimacy – is often missing inside organisations. Employees are expected to go along with change without being brought into the story. We talk about transformation but forget the human element.

Swift doesn’t.

She prepares her audience, builds anticipation and makes them part of the decision. In doing so, she creates loyalty that outlasts platforms, styles and even public backlash.

She pays attention ad she keeps delivering on that promise while still evolving. That’s what real trust is – not just consistency but consistency with progression.

Handle criticism. Use it. Grow anyway.

Speaking of backlash, Swift has had her fair share. But instead of retreating, she filters the criticism and uses it.

“Taylor is in a situation where I always say her career follows a modified version of Newton's third law: for every positive reaction there's an equal or greater negative reaction,” says Evers. “And it's been like this since the very beginning of her career. She's in a very public profession but there's something about Taylor Swift that tends to attract a lot of criticism and a lot of controversy. And she does find a way to manage through these things. And she does it in different ways.”

At the 2009 MTV Awards, for example, her idol Kanye West went on stage and essentially told her she was not good enough to be there. 

“Taylor did a few things based on this criticism. One, she took some of the criticism to heart and she got vocal lessons. And you can see how her voice did improve after that and her voice has continued to improve.  She also doubled and tripled down on what she's really good at. She didn't stray away from her core again. And you can imagine this is something that I think a lot of us would do. We're getting a lot of criticism, so we may retreat from what we're actually good at. It's really hard to.”

The same principle applies to organisations. Fear of failure and PR risk keep too many companies in defensive mode. But great leadership involves owning the story, acknowledging the setback and building something new from it.

Evers calls this ‘antifragility’. “I see resilience and antifragile as very similar but antifragile is a step above resilience. Resilience to me is, I got through an experience. It was really tough, but I made it through to the other side. Antifragile is, not only did I go through this bad experience or this challenge or this setback but at the end of it I feel like I'm stronger than I was when I started.”

Obsess over your people

Another standout lesson is Swift’s relentless focus on her fan’s experience. The Eras Tour runs for 3.5 hours. It spans 40 songs. That’s fan obsession.

“She could have played a two-hour greatest hits set and fans would have loved it,” Kevin tells me. Instead she went further. “She's always finding new ways to delight her fans and to help her fans feel more joy about her and her music.”

The parallel to work? We spend hours mapping customer journeys and product launches but barely give the same care to employee experience. We say people are our greatest asset but how often do we actually delight them?

Kevin puts it bluntly: “If you're in charge of people you need to feel it deeply and it needs to feel authentic to you to want to delight and bring joy to people's lives and to work as hard as possible to make that happen. I don't think that Taylor Swift would be as popular or as successful if she wasn't so obsessed with her fans and their experiences. And I think that's something that we can all take away from her.”

And he’s right. Too often, employee engagement is a quarterly report, not a day-to-day practice. We need more joy in work. Not just wellbeing apps and free fruit but moments that feel human, valued and considered.

Swift reminds us that design matters. Surprise matters. Thoughtfulness matters.

And when people feel it, they give more back.

Lead with instinct – when the foundations are strong

While many organisations talk about being data-led, Swift trusts something more human: instinct.

“She doesn't seem like the type that's sitting in a boardroom who's really trying to strategise like a chess grandmaster. She really tends to trust her instinct and wherever she wants her music to go that's the direction she moves in. And then she makes decisions from there. That's where her strategies come from,” explains Evers,

Her decision to fully pivot into pop, despite her label’s reluctance, wasn’t tested through surveys. It was a move based on clarity, trust in her own voice and a deep understanding of what her audience would follow her into.

This is informed intuition. And it’s something people leaders need to protect and model in themselves.

When you build deep trust and clarity of purpose you don’t need a dashboard for every decision. You need courage, focus and the willingness to act when the moment calls for it.

Build for the long game

While business obsesses over quarterly results Swift has always played the long game. From preserving fan trust to strategically timing album drops and genre shifts her moves are rarely reactive.

Swift doesn’t get up every day thinking, ‘I want to innovate’ but does what feels right for her music, her values and her audience. As Evers says: “When we talk about instincts it sounds so soft but instincts come from all of our experiences. They come from our emotions, all the things that we've gone through, all the decisions that we've made.”

That kind of thinking is essential if we want to move beyond burnout cycles and empty slogans. But it’s also a challenge. You can’t build long-term trust if everything is driven by short-term panic. And you can’t ask for innovation if you punish risk.

Swift plays a longer game than most leaders ever dare to. But that’s why it works.

So what can people leaders actually do?

Let’s end with Evers' top three takeaways for anyone in HR or people leadership trying to build better workplaces:

1. Trust and consistency are the foundation. You can reinvent but only if people believe the core won’t shift underneath them
2. Be genuinely people-obsessed. Go further than you need to. Think about joy. Think about delight. Make experience intentional
3. Adapt and overcommunicate. Don’t assume people know why change is happening. Tell them. Show them. Invite them in

Swift didn’t build a loyal fanbase by guessing. She did it by listening, leading and evolving – without losing herself along the way. If that’s not a model for future-fit leadership I don’t know what is.
 

🎧 Listen to the full conversation with Kevin Evers: Why Work Needs More Taylor Swifts, available now wherever you get your podcasts