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Storytelling For Leaders: Learn From The World’s Best Storytellers

Great storytelling is timeless.

There’s a famous Hopi Nation proverb that says “those who tell the stories rule the world” and it has never been truer than today with the viral power of the Internet spreading the most powerful stories all around the world with the click of a button.

The most successful leaders are often the best storytellers. While many people have diminished faith in politicians, economists, and priests; successful entrepreneurs who solve meaningful problems are the new role models of our era.

They give us a creative vision of what’s possible when you believe in something so strongly that you are willing to do anything to make it a reality.

We naturally gravitate toward great storytellers because they are the most interesting people. Today, with the power of Internet word-of-mouth any creative leader with a vision of a better future can use the power of storytelling to inspire at scale.

Why Learn Storytelling From Business Leaders:

The eternal problem in human affairs is a general lack of good leadership. People and the institutions we form are easily corrupted over time by groupthink and the lure of the comfortable mediocrity of the status quo.

The many problems in the world are great opportunities just waiting for those with the courage to step up and try to solve them. And today, individuals have the power to mobilize others into digital tribes with shared interests and values, globally-connected by a vision of the future.

An impact of great leadership is that it inspires us to become leaders as well. Each of the storytelling leaders highlighted below are entrepreneurs who have attempted to solve big problems and elevated the consciousness of millions of people, thereby inspiring more creative people to believe in the power of their dreams.

If you have your own creative leadership aspirations, then you should learn from the best role models. Each of the following storytelling leaders are role models that you can study and emulate to improve your own storytelling skills.

Here are some of the best storytelling leaders in the world today:

1. Richard Branson

Richard Branson Branding

British entrepreneur Richard Branson is the only individual ever to have built 12 billion-dollar companies in 8 different sectors, which is a remarkable feat that may never be duplicated.

The Virgin Group he founded in the 1970s now controls more than 400 companies in various fields, he regularly funds moonshots like Virgin Galactic and he is the most followed entrepreneur on social media websites such as LinkedIn.

From his private Caribbean island Necker Island, he presides over a global empire with brand storytelling at its heart. He disrupts entire industries based on the power of brand storytelling and creating better customer experiences than his competition.

Branson’s example makes the control freak CEO look like a relic of the past because of the trust he has in his team and his philosophy of delegation. Richard enjoys a healthy lifestyle of adventure with plenty of time for making videos and blogging by delegating to his team of personal assistants who deal directly with the leaders he hires to manage his businesses.

Recommendation: Read Branson’s autobiography Losing My Virginity to see what a billionaire storyteller thinks about business storytelling.

Great quotes:

1. “Brand storytelling is a great way to get your point of across, differentiate your brand, and work out new ideas. Today, if you want to succeed as an entrepreneur or leader, you also have to be a storyteller.”

2. “You don’t learn to walk by following rules. You learn by doing, and by falling over.”

3. “Business opportunities are like buses, there’s always another one coming.”

4. A business has to be involving, it has to be fun, and it has to exercise your creative instincts.”

5. “I have always believed that the way you treat your employees is the way they will treat your customers, and that people flourish when they are praised.”

6. “There is no greater thing you can do with your life and your work than follow your passions – in a way that serves the world and you.”

7. “Luck is what happens when preparation meets opportunity.”

8. “Capitalism – which in its purest form is entrepreneurism even among the poorest of the poor – does work; but those who make money from it should put it back into society, not just sit on it as if they are hatching eggs.”

9. “If somebody offers you an amazing opportunity but you are not sure you can do it, say yes – then learn how to do it later!”

10. “My philosophy is that if I have any money I invest it in new ventures and not have it sitting around.”


2. Elon Musk
Elon Musk Changemaker

Elon Musk is unique among well-known CEOs in his polymathic mastery across science, engineering, mathematics and philosophy disciplines. He has in-depth knowledge of the intricacies of physics, rocket science, space-age manufacturing, and battery technology that completely mystifies most people.

It’s rare for an intellectual or scientist to also have great leadership abilities yet Elon Musk has inspired millions of people to embrace logic and science, and tackle today’s biggest problems not with protest signs but by actually doing something about it.

He made himself a great storyteller by living a story worth telling and tackling some of the biggest challenges of our age with robot-like precision. When your goal is to save the world from the negative impacts of the fossil fuel economy, you need storytelling to motivate your employees to work the grueling 80-100 hour weeks that are necessary.

Musk brilliantly employs brand storytelling in his launching of new products and imparting his creative vision of the future in his regular live keynotes that spread his brand stories virally through both social media and the mainstream press.

Recommendation: Read his biography by American tech journalist Ashlee Vance Elon Musk: Tesla, SpaceX, and the Quest for a Fantastic Future.

Great quotes:

1. “The first step is to establish that something is possible; then probability will occur.”

2. “There have to be reasons that you get up in the morning and you want to live. Why do you want to live? What’s the point? What inspires you? What do you love about the future? If the future does not include being out there among the stars and being a multi-planet species, I find that incredibly depressing.”

3. “People work better when they know what the goal is and why. It is important that people look forward to coming to work in the morning and enjoy working.”

4. “Don’t confuse schooling with education. I didn’t go to Harvard but the people that work for me did.”

5. “No, I don’t ever give up. I’d have to be dead or completely incapacitated. When something is important enough, you do it even if the odds are not in your favour.”

6. “I’m not trying to be anyone’s savior. I’m just trying to think about the future and not be sad.”

7. “The Hitchhikers Guide to the Galaxy taught me that the tough thing is figuring out what questions to ask, but that once you do that, the rest is really easy. I came to the conclusion that we should aspire to increase the scope and scale of human consciousness in order to better understand what questions to ask. Really, the only thing that makes sense is to strive for greater collective enlightenment.”

8. “It is important to view knowledge as sort of a semantic tree — make sure you understand the fundamental principles, ie the trunk and big branches, before you get into the leaves/details or there is nothing for them to hang on to.”

9. “You get paid in direct proportion to the difficulty of problems you solve.”

10. “One of the really tough things is figuring out what questions to ask. Once you figure out the question, then the answer is relatively easy.”


3. Tony Hsieh

Tony Hsieh

Tony Hseih did what many people thought wasn’t possible.

He built a successful online shoe retailer called Zappos, which he sold to Amazon for close to a billion dollars and in the process he changed the world of customer experience.

After exiting with Zappos, he developed a creative vision to transform the dilapidated old Las Vegas downtown into one of the world’s premiere startup hubs. He also did something that other business leaders thought was completely insane when he implemented the radically disruptive Holocracy style of no bosses or hierarchy in his organizations.

He did all this by thinking big and telling great brand stories to investors, team members and customers. He knows that storytelling is key to building a transformative company culture, which is the best competitive advantage that any organization can have.

Recommendation: His book Delivering Happiness is one of the best business books ever written on creating transformative cultures in organizations.

Great Quotes:

1. “Happiness is really just about four things: perceived control, perceived progress, connectedness (number and depth of your relationships), and vision/meaning (being part of something bigger than yourself).”

2. “Envision, create, and believe in your own universe, and the universe will form around you.”

3. “I had decided to stop chasing the money, and start chasing the passion.”

4. “Personally I cringe at the word ‘leader.’ It’s more about getting people to do what they’re passionate about and putting them in the right context or setting. They’re the ones doing the hard work.”

5. “At Zappos, we really view culture as our No. 1 priority. We decided that if we get the culture right, most of the stuff, like building a brand around delivering the very best customer service, will just take care of itself.”

6. “I made a list of the happiest periods in my life, and I realized that none of them involved money. I realized that building stuff and being creative and inventive made me happy. Connecting with a friend and talking through the entire night until the sun rose made me happy. Trick-or-treating in middle school with a group of my closest friends made me happy. Pickles made me happy.

7. “We’re willing to give up short-term profits or revenue growth to make sure we have the best culture. In fact, after orientation, we offer people $2,000 not to work at Zappos. The ones who stay are right for our culture.”

8. “We believe that it’s really important to come up with core values that you can commit to. And by commit, we mean that you’re willing to hire and fire based on them. If you’re willing to do that, then you’re well on your way to building a company culture that is in line with the brand you want to build.”


4. Oprah Winfrey

Oprah Winfrey
President Barack Obama awards the 2013 Presidential Medal of Freedom to Oprah Winfrey during a ceremony in the East Room of the White House, Nov. 20, 2013. (Official White House Photo by Lawrence Jackson)

As a creative force and champion of living the life you want, Oprah Winfrey stands alone. She has hosted the highest-rated interview program ever, launched her own television network, and become a billionaire through the power of helping people share their stories.

It could be argued the Oprah Winfrey is the most influential woman in the world. She has a remarkable ability to bring out the most beautiful stories in people and to showcase the power of character.

Few people living or dead can rival her charm and interviewing skills. She is a master at helping other people tell their stories and her massive influence has launched the ideas of highly disruptive teachers like Eckardt Tolle to a global audience.

Recommendation: Her book What I Know For Sure is a modern classic.

Great Quotes:

1. “I see all art as a complement to telling people’s stories. I’m in the storytelling business. I believe that the humanity that all of us share is the stories of our lives, and everybody has a story. Your story is as important as the next person’s story.”

3. “Think like a queen. A queen is not afraid to fail. Failure is another steppingstone to greatness.”

4. “The more you praise and celebrate your life, the more there is in life to celebrate.”

5. “Turn your wounds into wisdom.”

6. “Passion is energy. Feel the power that comes from focusing on what excites you.”

7. “Be thankful for what you have; you’ll end up having more. If you concentrate on what you don’t have, you will never, ever have enough.”

8. Surround yourself only with people who are going to take you higher. One of the hardest things in life to learn is which bridges to cross and which bridges to burn.

9. “You don’t become what you want, you become what you believe.”

10. “You get in life what you have the courage to ask for.”

11. “The key to realizing a dream is to focus not on success but on significance — and then even the small steps and little victories along your path will take on greater meaning.”


5. Stuart Butterfield

Stuart Buttefield

Stewart Butterfield is a Canadian entrepreneur who co-founded the photo-sharing website Flickr and he is the founder of the team-messaging application Slack, the fastest-growing and most viral business app ever created.

He studied philosophy in University, a discipline shared by a disproportionately large group of highly successful entrepreneurs and investors in Silicon Valley such as Reid Hoffman of LinkedIn, Peter Thiel of Founders Fund and Paul Graham of Y Combinator.

As an entrepreneur, designer, and technologist he has spent his life building startups that empower people to share their art and communicate more openly. 

He actually stumbled across both of his big business ideas while pursuing his passion for multiplayer online role-playing games and trying to create more immersive video game experiences.

Recommendation: Listen to the Masters of Scale podcast on his Big Pivot.

Great Quotes: 

1. “If there’s one piece of advice I could go back to give myself, it is to concentrate on that storytelling part, on the convincing people. If you can’t do that it doesn’t matter how good the product is, it doesn’t matter how good the idea was for the market, or what happens in the external factors, you don’t have the people believing.”

2. The workplace of the future is hard to predict specifically, but one thing we can predict is that we will increasingly rely on human intelligence and creativity as opposed to human capacity to perform repetitive tasks.”

3. Every customer interaction is a marketing opportunity. If you go above and beyond on the customer service side, people are much more likely to recommend you.

4. Slack is actually a technical term in product management that means the excess capacity the system has to absorb any failures or to take on new work. That’s something that was really on our minds when we came up with it.

5. There’s a lot of automation that can happen that isn’t a replacement of humans but of mind-numbing behavior.

6. When we first started Glitch, there were four co-founders of the company. We built Flickr and worked together at Yahoo and then started Tiny Speck. We were split in Vancouver, New York, and San Francisco. So we used an old chat technology called IRC. Almost nothing went through email. That experience lead to Slack.

7. I had hippie parents, and I found it difficult to figure out how to rebel against them. For the first five years of my life, I grew up in a log cabin in coastal British Columbia in a very small town, like 300 people, mostly hippies. No running water, no electricity. When I was 12, I changed my name from Dharma to Stewart. At that age, you just want to be normal. 

8. Some people will know exactly what they want to do at a very young age, but the odds are low. I feel like people in their early- to mid-20s are very earnest. They’re very serious, and they want to feel like they’ve accomplished a lot at a very young age rather than just trying to figure stuff out. So I try to push them toward a more experimental attitude.

9. This is the greatest software development methodology: Don’t think about what you’re doing, have no ego. There’s no speculation.

10. When key users told us something wasn’t working, we fixed it – immediately.

11. The outward expression of empathy is courtesy.


6. Brian Chesky

Brian CheskyAn American billionaire who co-founded the peer-to-peer lodging service Airbnb, Brian Chesky built one of the most successful companies of startup boom in the last decade by disrupting the $500 billion hotel industry.

Like other startup founders who have built “Unicorns”, startups valued at more than a billion dollars, Brian Chesky and his billionaire co-founders Nathan Blecharczyk and Joe Gebbio are the rare exception in a startup industry where 95% fail and only 0.001% exit and become billionaires.

Airbnb and Brian Chesky’s leadership as CEO and Head of Community has been pivotal in the evolution of storytelling in the age of social media where customers are now part of the story and they can reshape and share it in a way that makes a product viral.

Recommendation: Learn about the power of brand storytelling and smartphone apps in this age of viral social media in The Airbnb Story.

Great Quotes:

1. “Culture is a thousand things, a thousand times. It’s living the core values when you hire; when you write an email; when you are working on a project; when you are walking in the hall. The stuff that matters in life is no longer stuff. It’s other people. It’s relationships. It’s experience.”

2. “Travel is a new experience that can transport you out of your everyday routine to create memories with the ones you love. Repetition doesn’t create memories. New experiences do.”

3. “Airbnb is different from most brands. We’re a community of individuals, and yet there’s a consistency holding us together through the values we share. We have a common belief in belonging, but everyone’s expression of it will naturally always be a little different.”

4. “The American dream, what we were taught was, grow up, own a car, own a house. I think that dream’s completely changing. We were taught to keep up with the Joneses. Now we’re sharing with the Joneses.”

5. “Build something 100 people love, not something 1 million people kind of like.”

6. “Our shared vision of belonging is the thread that weaves through every touchpoint on Airbnb.”

7. “The people with the passports, the people who travel more, tend to be the most understanding. And it’s ironic that the people who travel the least have the strongest opinions about the people they’ve never met.”

8. “No matter how certain I am about some culture or some group of people, my opinions are only as accurate as the amount of time I’ve spent with them.”

9. “When you start a company, it’s more an art than a science because it’s totally unknown. Instead of solving high-profile problems, try to solve something that’s deeply personal to you. Ideally, if you’re an ordinary person and you’ve just solved your problem, you might have solved the problem for millions of people.”


7. Phil Knight

Phil Knight Nike

Phil Knight and his co-founder Bill Bowerman started Nike in 1964 and built the greatest empire in American sports based around their trademark “just do it” brand story.

They built Nike into what it is today not by focusing on how great their shoes were but by telling the stories of the world’s greatest athletes and how they achieved their greatness while wearing Nike shoes.

They inspired a monumental personal growth and fitness industry in the United States, which has spread globally by empowering people to learn from the examples of athletes that a daily fitness routine is often the best medicine and fuel for growth.

Recommendation: Read his autobiography Shoe Dog, one of the best business books ever written.

Great Quotes:

1. “Life is growth. You grow or you die.”

2. “I’d tell men and women in their mid-twenties not to settle for a job or a profession or even a career. Seek a calling. Even if you don’t know what that means, seek it. If you’re following your calling, the fatigue will be easier to bear, the disappointments will be fuel, the highs will be like nothing you’ve ever felt.”

3. Nike is one company that embraces the power of the story. In 1970, Nike designated their executives “Corporate Storytellers” as part of their corporate culture. The stories the company leaders told ranged from recounting the company history —  “the Nike story” — to many tales of people simply getting things accomplished. By helping all their employees understand the company’s past, the stories help shape the company’s future. Imagine hearing the story of how Nike founder Bill Bowerman went to his workshop one day after a brainstorm session and poured shoe rubber into the family waffle iron. That was the birth of the famous Nike waffle sole. The telling of stories like this reflects “the spirit of innovation” at the shoe company, while connecting today’s work to Nike’s heritage and roots.

4. Whether it’s sharing a mission, selling shoes or inspiring a commitment to performance, storytelling is a powerful tool that can mean the difference between extraordinary status and being just another brand. More businesses are realizing what Nike has recognized: the power of storytelling. Business communication doesn’t just have to be bullet points, simple statements, or rhetorical rants. A dose of the human element, emotions, and branded thinking can result in a memorable message. Stories build messages that people care about. Stories help people bond to messages. People remember what they care about and bond with. When you engage listeners in a powerful, entertaining, and informative story, they remember it, and many times they ask for more.

5. “So that morning in 1962 I told myself: Let everyone else call your idea crazy . . . just keep going. Don’t stop. Don’t even think about stopping until you get there, and don’t give much thought to where “there” is. Whatever comes, just don’t stop.”

6. “When you see only problems, you’re not seeing clearly.”

7. “Like books, sports give people a sense of having lived other lives, of taking part in other people’s victories. And defeats. When sports are at their best, the spirit of the fan merges with the spirit of the athlete.”

8. “Have faith in yourself, but also have faith in faith. Not faith as others define it. Faith as you define it. Faith as faith defines itself in your heart.

9. “Like it or not, life is a game.”

10. “It’s not enough to do good things. You have to let people know what you’re doing.


8. Steve Jobs

Steve Jobs

Wait, isn’t Steve Jobs dead? Even from the grave, Steve Jobs remains one of the most influential people in the technology industry.

His mission to empower creative people with elegantly designed tools that were easy and fun to use was pivotal in the development of Apple, which is considered the #1 most valuable brand in the world.

His creative vision of a better fusion between technology and the Liberal Arts has transformed how we use our devices. His experience launching Pixar with a team of the world’s best storytellers taught him the power of business storytelling to craft a great brand story and empower brand evangelists to spread it.

Love him or hate him, his companies Pixar and Apple have set the “vision, values, and agenda of an entire generation that is to come” in the words of his biographer Walter Issacson.

Recommendation: The authoritative biography of his life is Walter Issacson’s Steve Jobs.

Great Quotes:

1. “The most powerful person in the world is the storyteller. The storyteller sets the vision, values and agenda of an entire generation that is to come.”

2. “People think it’s this veneer – that the designers are handed this box and told, “Make it look good!” That’s not what we think design is. It’s not just what it looks like and feels like. Design is how it works.”

3. “When you grow up you tend to get told the world is the way it is and your life is just to live your life inside the world. Try not to bash into the walls too much. Try to have a nice family, have fun, save a little money. That’s a very limited life.   Life can be much broader once you discover one simple fact: Everything around you that you call life was made up by people that were no smarter than you and you can change it, you can influence it, you can build your own things that other people can use.  Once you learn that, you’ll never be the same again.”

4. “Most people never pick up the phone and call, most people never ask, that’s what separates the people that do things from the people who just dream about them. You’ve got to act. You’ve got to be willing to fail. You’ve got to be willing to crash and burn.”

5. “If you want to hire great people and have them stay working for you, you have to let them make a lot of decisions. You have to be run by ideas, not hierarchy. The best ideas have to win. Otherwise, the good people don’t stay.”

6. “Death is very likely the single best invention of Life. It is Life’s change agent. It clears out the old to make way for the new. Right now the new is you, but someday not too long from now, you will gradually become the old and be cleared away. Sorry to be so dramatic, but it is quite true.

Your time is limited, so don’t waste it living someone else’s life. Don’t be trapped by dogma — which is living with the results of other people’s thinking. Don’t let the noise of others’ opinions drown out your own inner voice. And most important, have the courage to follow your heart and intuition. They somehow already know what you truly want to become. Everything else is secondary.”

7. “People say you have to have a lot of passion for what you’re doing and it’s totally true. And the reason is because it’s so hard that if you don’t, any rational person would give up. It’s really hard. And you have to do it over a sustained period of time.

8. So if you don’t love it, if you’re not having fun doing it, you don’t really love it, you’re going to give up. And that’s what happens to most people, actually. If you really look at the ones that ended up, you know, being “successful” in the eyes of society and the ones that didn’t, oftentimes, it’s the ones who were successful loved what they did so they could persevere when it got really tough.

And the ones that didn’t love it quit because they’re sane, right? Who would want to put up with this stuff if you don’t love it?”

9. For the past 33 years, I have looked in the mirror every morning and asked myself: ‘If today were the last day of my life, would I want to do what I am about to do today?’ And whenever the answer has been ‘No’ for too many days in a row, I know I need to change something.

10. Creativity is just connecting things. When you ask creative people how they did something, they feel a little guilty because they didn’t really do it, they just saw something. It seemed obvious to them after a while.

11. Technology is nothing. What’s important is that you have a faith in people, that they’re basically good and smart, and if you give them tools, they’ll do wonderful things with them.

12. The people who are crazy enough to think they can change the world are the ones who do.

Tell Your Story With Video

The fastest way to build your personal brand as a storytelling leader is through video storytelling.

Take my free 5-day Video Storytelling For Social Media challenge and learn how to film high-quality videos with your iPhone or Android smartphone.

The challenge covers a step-by-step process to get confident in making videos and how to create your own storytelling flow so you can quickly make unscripted videos.

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