Work's Not Working... Let's Fix It!

Why Work Needs More Taylor Swifts – Kevin Evers

Season 2 Episode 10

In this episode of Work’s Not Working… Let’s Fix It! Siân Harrington sits down with Harvard Business Review editor Kevin Evers, author of There’s Nothing Like This: The Strategic Genius of Taylor Swift, to explore what Taylor Swift can teach us about leadership, reinvention and making work actually work.

At first glance it might seem unlikely but Kevin argues that Swift is one of the most strategic thinkers in modern business. She’s mastered brand control, long-term trust and antifragile thinking in a way most organisations only talk about.

In an era where people feel disempowered, stuck in rigid systems and burnt out by constant change Swift’s playbook offers something rare: clarity, conviction and control.

From re-recording her music catalogue to turning setbacks into strategy, Swift’s approach holds powerful lessons for leaders navigating transformation, employee experience and brand loyalty.

Whether you’re a CEO, a people leader or someone questioning how to take back agency in your own career, this conversation will shift how you think about power, trust and the long game in work.

Key Takeaways:

  • Reinvention only works if you protect the trust. Swift has changed her genre, aesthetic and tone – without losing her audience. Leaders should take note.
  • Owning your story is the new power move. Swift didn’t fight for control – she built her own. That mindset shift applies far beyond the music industry.
  • Employee experience needs obsession, not just intention. Swift’s fan loyalty is built through care, consistency and surprise. Most organisations are still stuck at comms plans and pulse surveys.
  • Data can’t replace instinct. Swift’s biggest decisions weren’t based on algorithms – they were grounded in clear values and audience understanding.
  • Resilience is overrated. Try antifragility. Swift doesn’t just survive hits – she grows stronger from them. That’s a model more leaders need to adopt.
  • You can’t build long-term loyalty if you panic every quarter. Swift plays the long game. Business should too.

This episode is about more than Taylor Swift. It’s about taking bold, strategic ownership in a world of broken work models – and reminding ourselves that reinvention is a skill, not a risk.

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Kevin Evers (00:00)

We all work for organizations where people are trying their best and everyone's so busy heads down in their own work and it's really hard to build these types of communities and workspaces where people thrive and feel like they matter and feel like they're doing something that serves a higher purpose. And I guess the one thing I would say based on my research into Taylor Swift is it needs to be an obsession, right? 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. Because it is a job. It is really difficult to do. And if you look at Taylor she has millions of fans who all have very strong opinions about what she should be doing. And she continually finds new ways to delight them and that has to be a struggle for her to really try to come up with new ways to do that. Yet, it's the work that she's willing to do and 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.

Intro (01:21)

Hey, everyone. Welcome to Work’s Not Working, a show about forward thinking people leaders, innovators, and academics, and how they think we can fix work to make it more meaningful, healthy, inclusive, and sustainable. Brought to you by The People Space.

Siân Harrington (01:37)

Hi, I'm Sian Harrington. And today I'm joined by Kevin Evers, senior editor at Harvard Business Review and author of the fascinating new book, There's Nothing Like This: The strategic genius of Taylor Swift. Yes, you heard that right. Taylor Swift, global pop superstar, is the focus of a Harvard business book. And as Kevin makes clear, she's not just an entertainer. She's a master strategist, a bold decision maker and one of the most influential business thinkers of our time. 

What makes Taylor's story so compelling for anyone thinking about work today, especially people leaders, is the way she's navigated power, ownership, reinvention and connection in one of the most ruthless industries in the world. As Kevin puts it, she's not just resilient, she's anti-fragile. She gets stronger through setbacks. And she doesn't just engage fans, she builds trust and intimacy at scale. And she's made career moves with the kind of instinct and long-term strategy many CEOs would envy.

So later in the episode we'll explore how Taylor Swift redefined ownership by re-recording her own music and outplaying private equity. What her fan obsession can teach us about employee experience and internal culture. And why bold, instinct-led decision-making is more relevant than ever in a world increasingly driven by data. 

But first let me tell you a bit more about Kevin. Kevin Evers is a senior editor at Harvard Business Review, where he shapes books on innovation, digital disruption, creativity and leadership. He's also written widely on topics from Hollywood blockbusters to brain science. And now on how one woman built a billion dollar brand by doing work her way. So if you're curious about what Taylor Swift can teach us about work, stick around. This one might surprise you

Sian Harrington (03:42)

So welcome, Kevin, really delighted to have you on this episode. Now, you're a senior editor at Harvard Business Review, and it's not someone we'd naturally expect to write about a global pop star. So I wondered, what drew you to Taylor Swift, and what made you think that her career offered more than just entertainment?

Kevin Evers (04:00)

Taylor is operating in a very, very tough industry. That's the music industry. In the music industry, we tend to cycle through stars, even superstars, like their fashion trends. And Taylor has somehow found a way to stay relevant and to grow her popularity over these last 20 years, these two decades. And when I wrote the book, I didn't really approach her any differently than I would if I was writing about a great founder like Steve Jobs or Jeff Bezos. I think she's that good. And you don't grow to this level of success and popularity without having great entrepreneurial instincts and Taylor has great entrepreneurial instincts. And I also knew that her career was so full of ups and downs and challenges and opportunities.

So I was pretty confident that I could write a very fascinating book, an entertaining book. And what really drew me to her and the topic was I knew I could write in chronological order. I could position her career in chronological order so readers could see how she's evolved and adapted as the industry swirled around her. And that's a rare thing to be able to do. And I was really excited to be able to do that. 

Sian Harrington (05:18)

Yeah, it certainly is fascinating and entertaining. I can say that having read it. So I think there's quite a few lessons, definitely for businesses, for CEOs, for organizations here. So you describe her as one of the most strategic thinkers of our time. So can you talk me through, , maybe some decisions or what makes you think that perhaps a moment that. Perhaps a moment a CEO would understand and be impressed with?

Kevin Evers (05:43)

She's made a lot of bold decisions throughout her career and she recently made some very bold decisions. I always look at her re-record project as one of the boldest moves in music industry history. And as some of your listeners may know and some other listeners may not know, her master recordings were sold and she had no ownership over those albums. She was making royalties from those albums because she was a songwriter. But she didn't have full ownership over her first six albums. 

And she was not a fan of who those albums were sold to. They were sold to a man named Scooter Braun, who has represented Kanye West, and he's most famous for really finding and cultivating the career of Justin Bieber. And Taylor was not happy that he had owned her masters. And then Scooter went along and resold those albums to a capital investment firm called Shamrock Holdings. And Taylor saw no money from any of these sales. And she really had no leverage, 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 what does Taylor do? She decides to re-record all of her old music, those six albums. She ends up releasing four of those albums. And they were all largely successful. They all reached number one in the Billboard charts. And that was a really bold move because what she ended up doing is she ended up undermining the investment that others had made in her music. By releasing those Taylor versions, and those Taylor version albums they're streamed at a higher clip, they're purchased at a higher clip, she ended up undermining the investment that others had made in her music because the new music overtook the older music. 

And then she ended up buying back her albums too, those original albums. She did this very recently. That's a move that I think entrepreneurs or CEOs or anyone can really, I wouldn't say we could relate to it, but it's something that we can gain inspiration from it because we've never really seen this in the music industry before. And it's Taylor using her ingenuity, her creativity and her curiosity to reclaim full ownership of her music. And that's something that no one's ever really done at that scale before. Prince had threatened to do it back in the 90s. He had a famous battle with Warner Brothers. But those were idle threats. He never followed through with re-recording his music, but Taylor did.

Sian Harrington (08:15)

Yeah, it's a really bold move and particularly, I'm sure a lot of people who've been bought by private equity can understand that feeling of not having the control. But then to buy, as you mentioned, just recently buy back that catalogue as well is a very neat and clever move.

So this idea of control I think is something that comes out strongly from the book and is really interesting to us today in business. A lot of people don't feel they have much control at work. what do you think are the lessons that people can learn about how she's actually taken that ownership of her own narrative and her own career?

Kevin Evers (08:50)

For me, when I think of Taylor Swift, I think of two words. I mean, I think of many words, but in this particular topic, I think of two words. It's ingenuity and curiosity. Taylor's move to reclaim her older music was, it was ingenious in many ways. Like it was really creative and I don't think many other people had thought to really do it the way that she did it. And curiosity, think, is also really important too. She was really curious about what it would look like to re-record her old music. And she ended up following through. And this is something that Taylor’s done her entire career. Yes, she makes bold decisions, but she's hyper-curious. And I think that hyper-curiosity allows her to keep growing and adapting. And that's something we can all learn from. I know I've learned from it.

Sian Harrington (09:45)

Yeah, that's interesting. Do you think that this is something that could have backfired for her?

Kevin Evers (09:50)

Oh for sure. The re-record project is crazy if you think about it. It really is. What she decided to do is tell her fans, don't listen to that older music. The music that you had grown up listening to. The music that is so intertwined in your memories, in your experiences, in your emotions. Taylor had built her career on such a close relationship with her fans because of the way she sings and also the way she interacts with her fans. By re-recording her old music, I mean, she was threatening that relationship in some ways. And I'm thinking of my favourite bands. If Radiohead had decided, hey, we're gonna re-record OK Computer, we're gonna re-record Kid A, I don't know what I would think about that. Taylor made a pretty smart decision when she did re-record those albums she decided to not stray from the originals. She tried to create near-facsimiles of the originals, which I think was a smart move. But yeah, it totally could have backfired because her fans have such a close relationship with those songs. 

But I also think that Taylor has developed such a close relationship with her fans. It seems to be much closer than most artists have with their fans. And so her fans were willing to go along with this for no other reason that Taylor was not happy with who her re-recordings were sold to and her fans really wanted to rally behind her.

Sian Harrington (11:13)

I mean, that is absolutely amazing, isn't it really? I'm with you. If it had been a different take on it, you could see people wanting to get the new version effectively, but to keep it close to the original is an amazing step to take. And it shows something about her that's really good as well, which is how she keeps reinventing herself. And we've seen in music actually, probably more than in many other businesses, how those with the longevity, maybe you can go Madonna as another example, David Bowie, they keep reinventing themselves. 

She  shifted genres as well, hasn't she, in the music world, but she still kept to this core of herself. So how could that apply to companies who might be afraid of losing their identity? Because at the moment we're all having to completely reinvent our entire operating models. And it's very scary for people who've got a brand and an identity based somewhere else. What  lessons do think we can learn?

Kevin Evers (12:12)

Taylor reinvents herself, you're totally right. But I think she prizes trust and consistency above all else. And it all comes back to her fans. So even though she has moved from country music to pop music, to synth pop, to indie rock, 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. 

I always use the, there's a theory called ‘job to be done’, and that's as customers we don't just buy products, we hire those products to do something for us. And I think 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. 

If you listen to the deep cuts of those albums, you go beyond the big hits. They are vulnerable. They are intimate. And Taylor doesn't sing much differently than she did in the beginning of her career. It sounds like she's whispering secrets in your ear. So really she's using those genres, those new genre shifts to come up with new ways to express her emotions and to form that and deepen that connection with her fans. So she always stays very true to what she's good at and what her fans want from her. And the jumps and the reinventions only bolster those principles and those connections.

Sian Harrington (13:38)

Yeah, that's really interesting, isn't it? Because you've picked up on that trust and that customer, if we want to use the business term, that customer relationship. And as long as those are in place, we have seen businesses successfully move into totally different areas. As long as they've got that in place, if they don't, they can just lose everything. So that's a key lesson.

Kevin Evers (14:00)

Yes. Taylor is I call her fan obsessed. In business ee call a customer obsessed and I wouldn't say it's rare for an artist to be fan obsessed but I think the levels that she goes to is pretty rare. And I think as creatives and artists we tend to really focus on our craft and I think that's essentially, you really do need to focus on your craft, but Taylor has always been equally obsessed about her fans finding new ways to delight her fans, but also listening to her fans and really understanding what they want from her. And that's a big reason why she's able to make these shifts. It's a big reason why she's found such longevity because she never seems to lose track of that.

Sian Harrington (14:40)

Hmm. Interesting. So she isn't without her detractors. There's always some backlash against Taylor Swift. She seems to be able to use that as like a fuel for creativity really, she takes that criticism. And I think that's a really interesting thing for us in business, particularly for leaders, to take that as something that you can then  take the adversity and  build it into your brand and your journey and learn from it, etc. Is that something that you think is a lesson again that people could learn from Taylor Swift and her approach?

Kevin Evers (15:13)

For sure. 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. 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.

I look back to 2009, this was a huge moment in her career. She was really burgeoning into a superstar. She was going, she was a country musician, yes, but she was really starting to infiltrate the pop market as well. The MTV Awards in 2009, this is when Kanye West goes on stage, steals her microphone, and essentially tells her you're not good enough to be here, Beyonce is much better than you. And Taylor was 19 at the time. And she has since said that was a really devastating moment for her. And you can understand that she's in front of millions of people. And her idol, Kanye West, because at the time Kanye was considered this great innovator in rap music, tells her she's not good enough. And she was receiving a lot of other criticism around the time too. People didn't think her voice was good enough. They didn't think her performance was good enough. They didn't think that she deserved the level of popular criticism and awards that she was getting at the time.

So Taylor did a few things based on this criticism. One, she took some of the criticism to heart and she did go and she improved her voice 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 filter criticism and advice sometimes because we don't know what to take and what not to. But Taylor, even though she was getting criticized for being too teenage or for not having deep enough lyrics, for her third album after this criticism she decides to write the album all by herself. She doesn't use co-writers. And she ends up writing one of the most vulnerable and intimate albums of her career and not shying away from the subjects and themes that people are criticizing her for. 

And she turned that into promotional fodder. When she released that album she made sure that people knew that she wrote that album all by herself. And that's something that Taylor does really well and it is something we can learn from. It's filtering in the good criticism and knowing when to improve but also knowing that a lot of criticism that we face may not be coming from the right place. And we should double and triple down on what we're really good at times. And that's something I admire about Taylor. She does a good job of that.

Sian Harrington (18:13)

Do you think that some of the criticism came at that stage came from her age? Does some of this criticism come from her being a powerful woman? I mean, what do you think about that?

Kevin Evers (18:25)

For sure. This is a huge part of it. A lot of the criticism stemmed from the fact that who she was and who she was singing to. She was a teenager singing to other teenage girls and historically bands or artists that attract teenage girls tend to be met with a lot of criticism and scepticism and the Beatles were a prime example of this. And we all think of the Beatles as this huge phenomenon, especially when they came over to the United States. But the Beatles received a lot of criticism because we've all seen the videos of the teenage girls seemingly losing their minds. And a lot of people thought that, this can't be good music, right? Because the idea is that teenage girls, and we can even say women, when they listen to music, it's more emotional and it's not logical. 

Now, of course, that's all BS because any time any of us listen to music, it's both. It's emotional and it is logical at the same time. Bruce Springsteen fans have a very emotional connection to his music. Led Zeppelin fans have a very emotional connection to their music as well. 

And I do believe that this is a lot of the criticism that Taylor receives does stem from the fact that she's a woman and also the type of woman that she is. I always say that Taylor was probably the student in class who was sitting at the front and always raising her hand. She's a try-hard and I think that's a big reason why people are a little sceptical of her because she is talented musically but she also is a go-getter and she is ambitious and those things turn people off.

Sian Harrington (20:05)

Yeah, we still seem to be unable to deal with ambitious women wherever we are. And coming back to those fans what you talked about earlier is she's really developed this relationship where these fans think that they know her. It's almost like a friend, I think, to use your word, she's scaled this intimacy. And this isn't just about PR, is it? Which we can often see in business as a whitewashing of this stuff. But it does seem to be something really deeper and more strategic. How can you see that people being able to take that  thinking and put it into their own business so that it's more about employee engagement and internal culture that is actually meaningful and really is delivering rather than just being those words?

Kevin Evers (20:45)

Yeah, it's really hard to do. But Taylor has always tried to delight her fans and find new ways to delight her fans. I would say she sets high expectations and then she exceeds those expectations. And we saw this at the Eras tour. Taylor hadn't toured in four years at that point. The demand was really high and she could have played a two hour show, two and a half hour greatest hit show and her fans would have loved it. I'm sure they would have walked away joyous. But instead she plays three and a half hours. She plays a set list that spans 40 songs. And that had to come at great cost to her emotionally and physically. She was playing three nights in a row in many cities. It had come at great cost to her band and her crew and her dancers. Yet she followed through with it. And that's what Taylor does. She's always finding new ways to delight her fans and to help her fans feel more joy about her and her music. 

And I don't think many artists or many leaders are really willing to go so far to do those things. Because the way I look at it, it's like giving your toddler a popsicle before dinner. Your toddler will expect that popsicle before dinner all the time and then all of a sudden it's I want two popsicles, I want three popsicles and that's human nature. And that's the relationship she has with her fans. Her fans are always gonna expect more from her. Yet she has to have the confidence that she can not only meet their demands, but exceed those demands. 

I mean imagine playing three and a half hour shows. She had to think, well if I'm playing three and a half hour shows, that's gonna be the new expectations. That had to be a daunting thought for her. But again it all comes back down to her confidence and curiosity. I think she understands, or at least has the confidence in herself that she will continually be able to help her fans feel joy and delight in new ways. And I think that's something we can all learn from. 

We need to, yes, think about our jobs. We need to think about our craft. We need to think about the products that we're making. But I do think that it's equally important to think about the employee experience, but also our customer experience. And that's something that we need to be obsessed about. And that's what Taylor is.

Sian Harrington (23:03)

Yeah, I love those two words, joy and delight. think that's really great. And probably we do think a bit more about the customer when it comes to these things, trying to delight the customer. But I think in terms of the employee, we're not really looking at them in that way. Let's bring some joy, let's bring some delight. And I think we really need to in today's world.

And one word you use in the book, which I think is really interesting, is antifragile.

This is about coming back to that criticism in a way, this growing through pressure and coming back to joy and delight actually. We know that today and I've read quite a lot of Harvard pieces on this, that there's serious burnout, a burnout epidemic, if you want to call it that. I wonder how you see resilience versus anti-fragile? Are they connected in some way? Because she seems to do this bouncing back, this growing through being put in difficult situations. So I think there's some sort of correlation there that's interesting for us to learn from.

Kevin Evers (23:58)

I see resilience and antifragile as, they're very similar, but antifragile is a step above resilience. Resilience to me is, I got through an experience. It was really, 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.

And we see this all throughout Taylor's career. She has faced a lot of controversy. She's faced a lot of setbacks. Yet she finds a way to grow from those things. And we can go back to the re-record project for that. She was devastated when her albums were sold to someone who she didn't think those should belong to. And she lost control over that music.

And I think many of us would walk away with our tail between our legs and say I guess that's just the way it is. And that's what many artists have done throughout history because they didn't, traditionally they didn't have much leverage when it came to their master recordings. But Taylor did what only really Taylor could do and she re-recorded those albums and those albums did surpass the originals. Because of those re-recordings she was able to build up demand for the Eras tour. Because she had released two of those albums she was in the news all the time. She was constantly engaging fans and her fans were able to reacclimate themselves to her older music. And then she was bringing new fans along as a result. And that was a huge reason why the demand for the Eras tour was unprecedented because of those re-recordings. So there's Taylor being anti-fragile again. Something really bad happened to her but she parlayed that into the re-recordings, which created a demand for the Eras tour. And that's anti-fragile to me.

Sian Harrington (25:51)

Very, very clever. She's very inspirational. How much do you think it matters that she has a good support system around her? In the book do you pull out some things around the people around her, or is this very much about an individual who's just extremely impressive and very clever and very strategic?

Kevin Evers (26:10)

Taylor is at the top of the organization, no doubt, and a lot of what she does comes from her own instincts, her own gut instincts, and what she wants to do for herself and her music. But she does have a great team around her. Her management team, 13 Management, which she sits at the head of, is more secretive than the CIA. It's really hard to understand what's going on there. There haven't been any articles or any behind-the-scenes information about 13 Management. But she runs it like a family business. Her parents are actively involved. Her brother is actively involved. And she's worked with the same people that she's worked with since the very beginning of her career. So she seems very loyal and she keeps her team relatively small, it seems. 

She's also worked with great producers throughout her career. She's not the type of star that shops for hits or shops for producers – this is very common in the music industry. She's writing her own songs and she tends to work with a lot of the same producers. She develops long relationships with her co-producers. She hasn't worked with that many producers throughout her career, but once she finds one that she really clicks with she tends to work with those producers over three or four albums. 

I call her loyal with an asterisk. She's extremely loyal to the producer she works with but when she does feel like she needs to shift her sound or she needs someone new, she needs a positive shock into her creative system, she will move on to another producer. 

And I think this is a big reason for her longevity too, is that loyalty, is her commitment to the relationships around her. So many superstars have trouble moving from album to album because they're working with so many different people because they're not in full control of their own creative pursuits, but Taylor is, and I think she really values those relationships.

Sian Harrington (27:55)

That longevity is key, isn't it? But also being able to flex and move when the time is right. And talking about longevity or long, she is strategic. She has seemed to have played this long game, I would call it, looking at everything as a long journey. Whereas in business, we're obsessed with the short term, with those quarterly business goals etc. Is there something we can learn from that as leaders or is that just the way that the market is and we will never going to shift it?

Kevin Evers (28:27)

It's really hard to get past short-termism. It's a scourge on business. And I understand it. CEOs and leaders are beholden to their shareholders and Wall Street. The stock market tends to be very short-term focused. 

Taylor's in a different position. She's a company of one and she's not a publicly traded company. But what I admire most about her is that, and I have this quote very early on in the book, she received the Innovator of the Year award from iHeartRadio. And she gets up to receive the award and she's almost sheepish about it. And she said, I don't wake up every day saying I want to innovate stuff. I do what's best for me given the circumstances. And it just so happens that those decisions don't have prior precedent sometimes. So some of my best decisions are ones that no one has done before. 

And I think that's what makes her such a great strategic thinker is she makes very music-first decisions. She doesn't seem like the type that's sitting in a boardroom who's really trying to strategize 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. 

So I think that's why a lot of her decision making, it does seem like she's three moves ahead of everyone else. But in many cases, I don't think she is. I think she's just really making decisions that's what's best for her. And then she has the ability to adapt and pivot from there. And you can see this when she bought back her original recordings, right? Because she had spent so much time doing the re-recordings. And it worked. She did everything she wanted to accomplish, yet she still bought back that original music. And that's her ability to adapt and do what's right based on the circumstances, even though you could argue that that decision might have been a tough one because she had asked her fans to not listen to the old music. And then now all of sudden she's turning around and saying,  you know what? Never mind. You can listen to the old music now because I bought it back.

But this is what she does so well. She changes, she adapts, and then she really, really communicates. She makes sure that she communicates in a very clear and emotional way to her fans, and it works. Because even when she brought back that old music, there really wasn't any pushback. Her fans were celebrating and called the day that she brought them back Independence Day. So her fans are just so willing to go above and beyond for her because Taylor makes sure to include them in the decision making, at least after she makes the decision, she's really clear about why she does the things that she does. 

Sian Harrington  (31:07)

Instinct is an interesting word, isn't it? Because I think that we've moved a lot in business towards evidence and data and all of this type of thing. And instinct almost became a bit of a dirty word for a while. But I guess what I'm hearing from you is that that instinct is really key when you've got a strong  foundation to build it upon. And she seems to be able to just have that and a really strong customer trust and understanding with it. 

Kevin Evers  (31:28)

Yeah, think you said it right. Because Taylor has such a deep understanding of what she wants to do but also a deep understanding of what her customer, what her fans, want, I she's really more willing to make decisions based on instinct. And her move to pop music was a prime example of this. She could have her cake and eat it too for a long time. She was in country music, and then she was also, she was slowly infiltrating the pop market. It's a classic adjacency strategy in business. So she had two growth engines. 

And that's something that most brands or most companies would kill for. But instead, Taylor was like,  you know what? I'm listening to pop music. I love pop music. I'm really listening to 80s synth pop. This is really a direction I want to move in. I'm in my early 20s to my mid 20s. This is what my muse is telling me to do. 

And on paper, that was a risky decision because she was leaving behind country music, this genre, an industry that she had come up in and she had developed relationships in, yet she still decided to move to pop music completely. And that was a big risk. And she received huge pushback from her management team and from her label. 

Yet she persisted because she said, you know what this is the music I want to create and my fans will see right through it if I just throw on three or four country songs on this album. They will see that it's a commercial tactic and I can't do that to them. And that's what she did. She ended up making a full-on pop album. This was 1989, released in 2014. And it worked out. She ended up growing her fan base and growing her global appeal at the same time.

And to me, that was a largely instinctual move. But I think since she has such a, when we talk about instincts, it sounds so soft but instincts come from all of our experiences, right? They come from our emotions, all the things that we've gone through, all the decisions that we've made. And Taylor felt that very strongly that this is the move that she had to make. And it certainly worked out for her.

Sian Harrington (33:50)

And instinct's a good word in today's world of work where we've got AI coming up and taking all the other elements away from us but that's a very human characteristic to have. So you've immersed yourself in the world of Taylor Swift, in her work, in her decisions and everything. How long did it take you to pull the book together? 

Kevin Evers (34:07)

I started in early 2022. That's when the initial idea came to me. So before she had announced the Eras tour, was almost, yeah, it was about 10 months before she had announced the Eras tour.

Sian Harrington (34:21)

So having spent so much time immersed in this, has it changed anything about the way you think yourself about your own work or your own creativity or either leadership or the way you're working?

Kevin Evers (34:30)

For my entire career I've been very craft focused, like very focused on improving as a writer, improving as an editor, and that's really important. But I think what Taylor has taught me is that, yes, she's obsessed with those things too. She's a great songwriter. She's always trying to evolve and grow her craft. But again, she's like really smart at understanding that relationships are just as important. And I think I understood that but just following her career, it's really hammered that home to me. 

And for her it comes from a sense of humility, I think. She understands that superstars, in her case, aren't self-made. They're created by fans. It's a fan-generated phenomenon. And that's why she's so obsessed with delighting her fans over and over and over again and building the right relationships to build her career. 

And that's something that I think about daily at this point, that it's not just about being a great writer, it's not just about being a great editor, it's really about building and forming exceptional relationships. 

Sian Harrington (35:40)

Yeah, and we can, all of us in journalism or in writing can get caught up in that world of thinking about, as you said, improving that craft. And I think it's important to do, relationships, and again, today relationships are going to become more important as we face an AI-related type of workplace. And how's that actually played out in your own career? Can you give me an example of what that might mean to how you do something differently now?

Kevin Evers (36:06)

Well, I just put out a book and I think it's a really well-written book. I think it's entertaining. I think it's fascinating. But what I found is I need to build more fan relationships. And this is what I'm trying to do on social media. I'm trying to do it in other ways too. And it's putting in as much time to that stuff as I did the writing and it can be exhausting and can be tiring and you don't always see the results. When you write something really good you can see it on the page and yes, it was hard to do but then you see it and you feel great. But the relationship stuff is harder because you don't always see a return. 

And again, I'm pretty introverted. I can be personable and I can be charismatic when I need to be, but I get tired from a lot of social interaction. And it's not my natural instinct to put myself out there like that. And I've decided that I need to do more and more and more of that. 

When it comes to my own job, you I'm an editor and I acquire books and I have always known that it's a relationship business. I've always tried to cultivate great relationships with agents and authors. But after writing this book, I know it's something I need to double and triple down on because I can't say, I'm a great editor, I can really make your book great. I need to go above and beyond and really start to cultivate even more relationships than I have already.

Sian Harrington (37:34)

So true, and it reminds me so much of times that I've written something I thought has been really great and then like nobody's really known about it. And when you write, it's a great lesson for book writers as well, isn't it? You can't just bring out the book. That's the beginning of the process of making sure you build up, as you said, your fan base on it and get people out there to read it. 

So let's  end looking at some advice and lessons from you that you've got from the book. if we think about work today  people are, as I said earlier, under pressure. Quite a lot of people don't feel they can really speak up. They don't feel very empowered. Is there like a story from Taylor's career that you think you could really inspire us to maybe be a bit bolder, a bit more courageous to have that curiosity you've talked about?

Kevin Evers (38:19)

I go back to the very beginning of her career. She's 13, 14, 15 years old. And you could imagine being in that situation must have been very challenging. In many cases, she was a young girl in songwriting rooms with men three to four times her age. But what surprised me the most about that period of time was what a clear vision Taylor had. She really knew the artist she wanted to be and she knew the audience she wanted to hit. And that was not the consensus in country music. 

We can look back and say, of course she was successful. She looks like she's out of country music central casting, the blonde hair, the blue eyes, the boy eating attitude. But she was an underdog, anyways, because country music did not think that there is room for a teenage girl writing her own songs. And they did not think that there was a market worth going after in the teenage girl market because they have the data and the failed experiences to prove it.

But Taylor really, really persisted. And I don't think we'd be sitting here today talking about Taylor Swift if she hadn't persisted and if she hadn't had such a clear vision for what she wanted to do. 

I think this goes back to that instinct word, instinct. She really knew deep down that this is what she should be doing. And she received a lot of pushback, a lot of pushback, yet she kept going because she did have such a deep instinct for the fact that she should be writing her own songs and she should be writing those songs for an audience of her peers.

And that's something that I have taken away from this because any creative endeavour, any career, is full of so many ups and downs. It's full of so many pushbacks and criticisms and people questioning or being sceptical of your ideas. in some cases that scepticism is perfectly legitimate but in other times it's not. And I always joke with my wife I should make ‘what would Taylor do’ bracelets, because it's really inspiring and empowering to look back at her career and see how bold and how courageous she was. And that's something I would definitely take from her. And I think that others can take from her as well.

Sian Harrington (40:33)

I think you'd have a good market for those bracelets. You're alluding to that bit in the book that is extraordinary really, where as you said, she's so young and she's got these people who want to write a certain way for her. And she just, I can't remember the exact way you say it, but this is not what my mark want, this is not what people my age want to hear. These are not the lyrics that work.

Kevin Evers (40:53)

Yeah, it's the opening story of the book. She's 13 years old. She's with these professional, great Nashville songwriters. And they're trying to push her in a certain direction. And she's like, no, that's trite. That's not what my friends would say. So we can't use that lyric. We need to say it in a different way. And that's, I almost didn't believe it when I was writing it, when I found those stories because it seems extreme that someone so young would have such a clear idea of what she wanted and be bold enough to speak up for herself. You can see the reason why I started with that story is you can see the makings of Taylor Swift. You could see her character traits. You could see her attitude in place when she was so young. And you could see how those character traits and those attitudes really helped her throughout the course of her career.

Sian Harrington (41:45)

So, words that jump out to me  having read the book and discussing it now: the reinvention, autonomy, the fact of the curiosity, as you said, obviously she's a storyteller. These are words that we're hearing a lot and I'm sure you'll concede come up quite a lot in a Harvard book or in an HBR story. We have a lot of HR and people leaders who listen to this podcast, how can we, what advice would you give them to how we could build a workplace where these are not just buzzwords, that these actually can be reality?

Kevin Evers (42:15)

It's so hard, right? We all work for organizations where people are trying their best and everyone's so busy heads down in their own work. And it's really hard to build these types of communities and workspaces where people thrive and feel like they matter and feel like they're doing something that serves a higher purpose. 

And I guess the one thing I would say based on my research into Taylor Swift is, and we've talked a lot about this, is it needs to be an obsession, right? 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. Because it is a job, it is really difficult to do and if you look at Taylor she has millions of fans who all have very strong opinions about what she should be doing. And she continually finds new ways to delight them, and that has to be a struggle for her to really try to come up with new ways to do that. Yet, it's the work that she's willing to do. And 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.

Sian Harrington (43:40)

So if we had to sum up your  top three leadership lessons that the story about Taylor Swift gives us to help make work better, which is what we talk about in this podcast, what would your top three be? I think I can guess some of them, but if you were to sum up, what would your top three lessons be?

Kevin Evers (43:58)

It all starts with trust and consistency. Taylor's always privileged those things. She surprises her fans, but she never shocks them. And I think she's always very clear about what her fans may want or what they might not want. And so those connections are really important to her. 

Fan obsession, again, this is tied to the first one, I think is critical. We can call it customer obsession, just going above and beyond for other people and not just letting the work speak for itself. 

And the third one is to adapt and evolve depending on the circumstances. To not feel like, some things may be working over time, but that doesn't happen forever. And I think it is really important to adapt and evolve. 

And if I get add a fourth one, it's what Taylor is really, really good at, and that is over-communicating. In the arts, I don't think many artists like to communicate why they make certain decisions but Taylor has always acted more like Steve Jobs than a Bob Dylan, so to speak, and she's always really, really good at communicating why she makes certain decisions, and I think that's critical to her success as well.

Sian Harrington (45:12)

Great, fantastic lessons there. And I think the comparison with Steve Jobs is a good one. And you're a Radiohead fan. Were you a Swift fan? Are you now a Swiftie? 

Kevin Evers (45:22)

I was a casual fan in the beginning. When I was in my early 20s, Taylor had just released her first album. So it would have been a little odd for me to listen to her debut album since she was this 16-year-old girl singing about teenage girl problems, which I didn't relate to. 

But later on in her career I did jump on the bandwagon. There were some albums that I really loved, Reputation and Folklore were two of them. So yeah, I was always a casual fan. But I have to say, after writing this book, after listening to her music over the last two or three years, I am a hardcore fan. It's really hard not to be. There's a lot to be impressed by with Taylor Swift.

 And I know a lot of people look at Taylor, they see the sequins, they see the glitter, they see the Louboutin boots, and they don't see someone who's really bold, but she is. She makes punk rock decisions, and there is something there for all of us to learn and we can all feel inspired and empowered by Taylor Swift. 

Sian Harrington (46:23)

I couldn't agree more. I love Radiohead myself. I like Taylor Swift's music. I wouldn't say I was a massive fan, but one thing is for sure –you have to admire her. I think she's done an amazing job. Her control, as you said, her empowerment, her instincts are so fantastic. And I'm delighted that you've walked us through her story today and pulled out those lessons. So thank you very much for being on the podcast. I really enjoyed it.

Kevin Evers (46:50)

Thanks for having me. I appreciate it.

Siân Harrington (46:52)

That was Kevin Evers, sharing what the career of Taylor Swift can teach us about power, purpose and performance in the workplace.

What really stayed with me from this conversation is that phrase fan obsession.
Because while many companies say they care about employees, few actually work as hard as Taylor does to delight them – consistently, intentionally and with deep understanding.

And if she can pull that off while playing 3.5 hour shows and reinventing herself every few years… maybe it’s time we upped our own game.

If you want to dive deeper I highly recommend Kevin’s book There’s Nothing Like This. Even if you’re not a Swiftie, you’ll find smart, strategic lessons in every chapter.

Thank you so much for listening to Work’s Not Working – Let’s Fix It! Don’t forget to subscribe wherever you get your podcasts, and follow me, Siân Harrington, on LinkedIn

For more bold ideas on the future of work and leadership, visit www.thepeoplespace.com.

This episode was produced by Nigel Pritchard.

Until next time: stay bold, stay curious, and keep fixing what’s not working. Goodbye.

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