10 Leadership Lessons from Celebrities

Celebrities can (sometimes) do more than entertain. Occasionally, their stories and struggles can offer us insight as we work to build our own dynasties in our niche. Looking at their shortfalls and success can help us gain valuable insight on what it truly means to be a leader.

  1. Oprah Winfrey – Leaders need patience

Oprah Winfrey is one of the most successful rags-to-riches stories of our time. Born into poverty, she overcame personal challenges and found her first media job at age 19. It took several years before she launched her talk show, and several more before her own network found success. When she created her network, everything was in place for immense and rather immediate success. She had the masses of fans. She had the industry experience. She was highly networked. She could afford to help finance it. But the network took years to take off. Even Oprah Winfrey, a queen in her industry, needed time to make things happen.

As you lead your organization, try not to get too discouraged over setbacks. Perseverance is important to getting your company where you need to go. Your staff looks to you for guidance and encouragement. Lead the way with a determined enthusiasm and dedication to working to get your company where it needs to go.

  1. Bear Grylls – Leaders encourage risk taking

Bear Grylls is a well-known adventurer, writer, and TV personality. In his show “Running Wild with Bear Grylls” he takes a new celebrity on an adventure, encountering obstacles from crocodile infested waters to repelling down cliffs. As he coaches celebrities, he encourages them to take calculated risks. It’s not a throw caution to the wind and be reckless strategy, but rather a “nothing risked nothing gained” perspective. He works with the celebrity, understanding their strengths and limitations, and then encourages them to push their boundaries. He serves as their safety net, ready to step in as needed. But, his focus in on getting them to stretch their limits.

Good leaders empower their workers to grow and go beyond their limits. Along the way, they serve as a valuable resource, of course. Good leaders train their employees with all the information they need before giving them the gentle nudge to go off on their own to take calculated risks. Whether you are helping someone survive crocodiles or pitch an unconventional idea, good leaders encourage risk tasking.

  1. Emma Watson – Leaders manage their own imposter syndrome

Emma Watson is a famous actress, model, and activist. She is wildly successful and talented, but even she is not immune to self-doubts. Watson is one of the many celebrities vocal about their own struggles with imposter syndrome, a frustrating challenge where a highly capable individual doubts their own ability. Often, people with imposter syndrome feel as if they are faking their way through their work or life, just waiting for others to realize they are incompetent. Ironically, it’s those who should be the most confident that struggle with imposter syndrome. Emma Watson speaks often about her own struggles and how she works to manage them.

As a leader, you may experience crippling self-doubt. As an entrepreneur, you get an extra helping of insecurity. So many people are counting on you and at times it can feel like you are beyond your depths. Letting these fears stop you from acting or affect how you work can be damaging to your business and your employees. Proactively managing imposter syndrome helps you be a better leader.

  1. Vince Lombardi – Leaders show, not shout

Vince Lombardi is one of the greatest professional football coaches of all time, leading the Green Bay Packers to victory time and time again. You can get lost reading through a collection of his quotes, as each one is an inspirational landmine. When talking about coaching, he famously said “they call it coaching, but it is teaching. You do not just tell them…you show them the reasons.” Lombardi took the time to explain to his players the reasoning behind his choices and strategies, rather than simply yelling orders. This, arguably, helped improve the coach-player relationship, team cohesion, and the players’ motivation (especially when things got rough).

  1. Lana Del Rey – If It’s Not Working, Reinvent Your Brand

Before she found fame as a 1960s-inspired sultry throwback singer, Lana Del Rey was a prep-school graduate from upstate New York named Elizabeth “Lizzy” Grant. She started her career with her given name, blonde hair, no shtick and an acoustic, folksy vibe. But, that wasn’t working. So, she reinvented her career under the stage name Lana Del Rey, dyed her hair, adopted the 1960s makeup and deep voice and had a breakthrough.

If your business isn’t standing out, consider going from Lizzy to Lana — give your location, products or services a makeover and use a bold, high-styled appeal to set yourself apart in a crowded marketplace.

  1. Miley Cyrus – Love Your Customers and They Will Love You

Miley Cyrus loves her fans so much that she has nicknamed them “Smilers” and makes sure to acknowledge them often, whether on tour or on social media. This is a great strategy for your business — it is much easier to market more products and services to your existing customers that are already raving fans than to try to find new ones.

So, make sure your customers know that they are loved and keep telling them. Doing this will create customers who will buy more from you and advocate for you — loyalty is the way to go.

  1. Justin Bieber – Go Niche

Many of us don’t understand the appeal of Justin Bieber (make that really don’t understand the appeal…), but it doesn’t matter because we aren’t his niche. He appeals to tween and teen girls. They love him and he knows how to leverage that, without worrying what everyone else thinks of him.

Your business can borrow from the Biebs by focusing on a very distinct target market and knowing what that market cares about. I remember a very successful shoe store in Chicago that employed a similar strategy. They had only really attractive young men working there, who flattered every female customer incessantly as they tried on shoes. That store did very well. Once you are solid in knowing your target market, find a hook that has a strong appeal to them.

  1. The Kardashians – Strike While the Iron Is Hot

To say that the Kardashians have not been shy about exploiting their brands is like saying that fire is kind of hot. The Kardashian girls endorse clothing, makeup, perfume and more. What they know is that no business cycle lasts forever, so they are not shy about maximizing their potential while they can.

The same goes for your company. Business cycles are shortening, so don’t be afraid to make the most of your opportunities while you are hot.

  1. Lindsay Lohan (And Some Other New Celebrity Just About Every Day) – Even a Good Brand Can Become Tarnished

Even if you have something valuable to offer, if you are a jerk, eventually folks won’t want to do business with you. Alec Baldwin, Tiger Woods and Lindsay Lohan are just some of the celebrities that have learned this the hard way.

  1. Geraldo Rivera – Future success cannot be built on past accomplishments.


Watching Geraldo Rivera bomb five tasks in a row was amusing and sad. Frankly, Geraldo’s ideas were good — 10 years ago, but did not resonate with company executives who were looking for forward thinking, innovative ideas that appeal to today’s consumers. Not to detract from his achievements, but Mr. Rivera thought that his past journalistic success would lead his team to winning each challenge; it did not. In fact, many younger people do not even know who he is. Geraldo is a forceful, strong-willed personality who does not take “no” for an answer. Maybe that’s the reason behind his success; however, when working with or leading a t-e-a-m, there has to be collaboration. Most of Geraldo’s contributions focused on “I am an award winning journalist,” “I’m Geraldo Rivera.” “I should be the one in front of the camera.” The recurring theme was “I,” a terrible mistake for a leader, manager, or anyone in authority to focus all the attention on himself or herself without having any regard for team members’ input.

You can’t get complacent in your business — you need to continually work to earn the trust and respect of your vendors, clients and employees. If you don’t, you may find opportunities drying up, or altogether disappearing.

Good leaders do more than order their employees around. Taking the time to explain the mindset behind your decisions can leave an impression on your employees. It shows you value their opinion and understanding enough that you would spend the time talking to them. It helps them understand the values behind your decisions (i.e. I really value this client relationship, so I want to go overboard in correcting their customer service issue). It opens up dialogue so employees can feel free to express their confusion or differing perspective. Showing your employees the reasons behind what you are asking them to do or the reasons for your choices can help strengthen your business.

Not all celebrities are good leaders. But some stand above the crowd, offering unique ways to lead that translate well into business. As you lead your organization, think about ways you can implement these tactics to be a more effective leader.