Swift Success: Leadership Lessons from Taylor Swift’s Journey 

Swift Success: Leadership Lessons from Taylor Swift's Journey 

Table of Contents

  • Hannah
  • November 29, 2023

Have you been to the Eras Tour yet? Or maybe listened to Swift’s latest re-recording of 1989 (Taylor’s Version)? Taylor Swift is more than a musician, singer, and songwriter. She’s one to look up to, and we bet you (secretly) do!

In this article, we’ll spotlight the leadership lessons from Taylor Swift that staffing firm leaders and content leaders can apply in their journey, to be more effective and impactful in the competitive business world. From her taking a stand to addressing gender bias, let’s have a look at how Swift’s actions can offer you valuable insights into your industry.

Out of the Woods and Into A New Era: Taylor Swift Today 

From Taylor Swift’s long list of awards to her ranking in numerous lists, such as being number 34 in Forbes’ America’s Richest Self-Made Women in 2023¹ and number 79 in The World’s 100 Most Powerful Women in 2022,² everyone knows how glorious, influential, and intriguing her life has been whether you’re a fan or not.

Forbes estimates she’s now worth more than $1.1 billion, an increase of $360 million from June 2023 when she ranked in the Self-Made Woman list.³ Most of her recent earnings came from the success of her Eras Tour and the screenings of her movie Taylor Swift: The Eras Tour.

What’s so special about Swift’s rise to billionaire status is that she earned solely from her phenomenal music career, unlike her colleagues with other side hustles to boost their earnings.

Related Reading: Unlocking Taylor Swift’s PR Secrets: A Guide for Content Marketers and Staffing Firms 


…Ready for It?: Leadership Lessons from Taylor Swift 

What makes Taylor Swift different and successful are her values that can influence industry leaders. Let’s have a look at them and see what you can apply for yourself.


1. Communicate your values.

Remember the iconic Katy Perry-Taylor Swift reunion in the You Need to Calm Down music video? It’s so iconic, but that’s not even the best part of it.

What’s great about it is that Swift used it to vocalize her support of the Equality Act. This Act would protect LGBTQ+ people from discrimination in homes, schools, workplaces, and other public accommodations.

The music video featured known LGBTQ+ individuals such as singer-songwriter Hayley Kiyoko, Youtuber Hannah Hart, and television personality RuPaul.

As a leader, you can use your company’s platforms and communication channels to share your values and purpose through thought leadership. Speak up and share what’s important to you and establish your expertise about your chosen values. This way, you can positively influence people and help them become more knowledgeable about essential matters.

On top of this, thought leadership can also positively impact your brand, encouraging them to explore what you have to offer.


2. Build strong, genuine relationships through empowerment.

Taylor is a collaborator; many of her friends, such as Ed Sheeran and Paramore’s Hayley Williams, have been featured in her songs and music videos a few times. This is because she has built connections with them and can now rely on them to help her make her new ideas come to life.

Of course, let’s not forget about her fans. Taylor gifted them glowing bracelets at her concert’s admission to show some love. It might seem like a tiny gesture, but her fans totally loved it—they felt this incredible connection with her.

Genuine connections can lead to trust, which is needed to become an effective leader. Start building trust in your relationships by being reliable and open. Be there when your co-leaders or teammates need you. For example, you can provide feedback when necessary and be open to suggestions and casual conversations.


3. Be adaptable and flexible.

Swift started in 2006 as a country singer, and people loved her for it. Over her subsequent albums, she decided to branch out and slowly shifted to pop music.

Trends and people’s interests change in every industry, and you must be flexible enough to address your audience’s needs. Just like Swift, there may come a time when your organization has to change its offerings slowly. Don’t hesitate to explore your possibilities, and you’ll find something new to offer.


4. Overcome challenges with resilience and perseverance.

You probably know Swift is rerecording her old albums due to a copyright issue in 2019. Scooter Braun snagged Big Machine Records, Swift’s old label, giving him control of her original recordings. This meant anyone wanting to use Swift’s songs had to pay Braun, not Swift.

So, Swift started re-recording her music, kicking off with Fearless (Taylor’s Version) in April 2021 and then dropping Red (Taylor’s Version) the same year.

In staffing and leadership, hurdles are part of the game. How you face them can shape your journey. Swift’s battle to regain control of her old tunes is a lesson. You can come out on top in tough times with the right strategies and support. The key? Don’t throw in the towel too soon—that resilience starts with you.


5. Listen to your team members’ concerns.

Swift’s genuine connection with her fans, the Swifties, allows her to communicate with them. She listens. When rumors circulated on TikTok about Swift not liking her Evermore album, she didn’t let it linger. Swift addressed the speculations onstage before diving into a song from the album.

As a leader, tackling your team’s concerns head-on is crucial. They’re part of your crew, and whatever’s on their minds can have ripple effects. Be kind and truthful in addressing issues and be open about your perspective to help them better understand the situation.


6. Empower people by fighting for what’s right.

Taylor has been known to fight against gender bias. One remarkable instance is when she called out Ginny & Georgia, a Netflix series, in 2021 about a scene that said, “What do you care? You go through men faster than Taylor Swift.”

She called this scene a lazy and deeply sexist joke and then ended her statement with a greeting of, “Happy Women’s History Month I guess.” The comedy show faced significant backlash as a result.

Leaders like Swift have the power to stand up for what’s right. Empower your team members to speak out against mistreatment. If you see anyone being mistreated, fight for them. You can also do this by continuously educating your employees about what matters, such as about diversity, equity, and inclusion.

Fostering a workplace culture that values and champions these principles allow you to contribute to a more respectful and inclusive environment.

Related Reading: Leadership Lessons from F1’s Dominant Force: Insights from Mercedes Team Principal Toto Wolff 


Swift is a Leader to Look Up To 

Swift’s journey emphasizes leadership lessons that can be valuable to both established and aspiring leaders. She’s navigated a dynamic industry with her resilience, authenticity, and adaptability, allowing her to embrace the power of change.

She’s also committed to fostering genuine connections and self-expression, showing how important emotional intelligence is to leaders.



Taylor Swift doesn’t let the haters get her down – she shakes it off and keeps leveling up her leadership style. As a thought leader or staffing firm leader, you need that resilient mindset when building your brand. If you want to tap into your inner Taylor and boost your marketing game, Allied Insight can help.

Our executive coaching will make you fearless at forging swift-style strategies that connect with your audience. Let’s chat about how we can help you leverage Taylor’s secret sauce to build a bandwagon of loyal followers. It’s time to shake things up!



1 “America’s Richest Self-Made Women.” Forbes, 1 Jun. 2023, www.forbes.com/self-made-women/?sh=4d5710ab6d96.

2 “The World’s 100 Most Powerful Women.” Forbes, 6 Dec. 2022, www.forbes.com/lists/power-women/?sh=158c515d5a95.

3 Dellatto, Marisa. “Taylor Swift’s New Era: The Pop Star Becomes A Billionaire.” Forbes, 27 Oct. 2023, www.forbes.com/sites/marisadellatto/2023/10/27/taylor-swifts-new-era-the-pop-star-becomes-a-billionaire/?sh=fc2a2305dee8.


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