Your Leadership Story: Develop It and Share It Often

amazing leadership stories

This past winter, I had the wonderful creative opportunity to act as writing coach and contributor to the just-published Life is Good: The Book (How to Live with Purpose and Enjoy the Ride). It’s a fun and inspiring celebration of the power of optimism, written by Bert and John Jacobs, brothers and co-founders of Life is Good. Through moving, funny, and engaging stories, the brothers chronicle their personal and professional journeys as they take a simple idea and fashion it into one of America’s most well loved, widely admired and socially-conscious clothing and lifestyle brands.

We talked a lot about the power of leadership stories as we wrote the book – their ability to create powerful personal connections, to build trust, to reveal our character, our dreams and intentions, to draw others to our causes and endeavors. One conversation about the surprising recent popularity of public storytelling found its way into the book. Few these days haven’t heard about – or listened to – The Moth Radio Hour. Every week, tens of thousands across the country flock to live storytelling venues, and millions more listen on the radio as a lone human being steps up to a microphone and tells his or her candid, revealing personal story. Think about it. In this day of dazzling multimedia and visual entertainment where stunning computer-generated graphics and fantastic action sequences dance before our eyes, a lone storyteller on a bare stage still somehow has the power to hold our attention.

Stories are powerful. Always have been. Humans have gathered in caves, huddled around campfires, shared across the dinner table, or listened in the late hours when the party has wound down, our guard is down too, and the stories really get interesting. Like the Ancient Mariner, we can’t seem to help ourselves. We’re compelled to tell stories, to make sense of our experiences, and ourselves. More than that, stories connect us. My story becomes our story by embedding messages about our values, our identity as a group. Stories help shape the culture you want to create as a leader. Think of the oft-repeated stories so many families tell around the dinner table at gatherings at special gatherings. Some are immigrant stories, hardship stories, stories of a grandfather or grandmother, a father or mother or brother who met and overcame significant challenges. These stories create a common language, shape our view of ourselves, remind us what truly matters, instill pride and ambition, bond us.


The best leaders have always been aware of the power of stories and have used them naturally and authentically in a variety of ways and for many powerful purposes. If we scan history we find again and again that successful leaders – politicians, corporate and community leaders, leaders of social movements – are great storytellers. Lincoln used seemingly simple homespun stories with profound lessons embedded in them. Franklin D. Roosevelt wove them into his Fireside Chats. Martin Luther King Jr.’s dream was at heart a journey story. Ronal Reagan was a storyteller of wit and charm. Barack Obama’s rise to prominence was strongly aided by his compelling autobiography, Dreams of My Father: A Story of Race and Inheritance.


Many of today’s most successful business leaders are compelling storytellers as well. Want to learn from them? Pick up Starbucks CEO Howard Schultz’s autobiography Pour Your Heart Into It or Barbara Corcoran’s Shark Tales. Pick up Richard Branson’s Losing My Virginity, Sheryl Sandberg’s Lean In, Yvon Choinard’s Let My People Go Surfing, and many more. Pay attention to the functions of their most compelling leadership stories – drawing us in, establishing trust in their character and intentions, revealing their passions and purpose-driven work, creating connections. Their individual stories become collective tales that make us want to join them, to engage, experience and invest in their movements, ideas and brands.


One common leadership story is the founding story. Really, it’s an origin story. Just as cultures and religions shape their origin stories to tell themselves how they came to be, how they are unique, and what they value, people do too. In Life is Good: The Book, we learn that on the company’s tenth anniversary, Bert and John Jacobs decided to place a simple version of their early years on the hangtags attached to every piece of clothing they sold. They referred to it as their “heritage story:”


For five years, Bert and John Jacobs designed and sold t-shirts in the streets and in college dorms up and down the East Coast. They slept in a van, lived off of peanut butter and jelly sandwiches, and showered when they could. The ladies were not impressed. With a combined total of $78 in the bank, they thought about giving up their dream. Until three simple words showed them the way: Life is good.


Initially, they balked at putting the story out there. After all, many successful people start out in humble ways. They decided to try it for a year. As they explain in Life is Good: The Book,


“But then our retailers and customers told us what it meant to them. How they connected to the story of two regular guys stumbling their way along and forming a company based on their beliefs. They liked the fact that we’re still running the company too. The story is important to people because it’s authentic, they told us. Keep sharing it. So we do . . .


“You have a “heritage story” too. Each of us has a unique journey marked by experiences that shaped who we are. Reflecting on those formative stories occasionally can sharpen our understanding of where we came from, where we struggled and fell down, what we learned, and what we have come to value most. And when you share your story openly with others, they get to know who you actually are. These shared, authentic stories help us all build trusting relationships.”


I have worked with hundreds of managers and leaders, helping them craft and practice their leadership stories. One ready source is what leadership guru Warren Bennis called “crucible stories.” A crucible is a trial, a test, something you go through with difficulty that teaches you a great deal. Challenges that lead to new learning are often a great source for leadership stories. Among the simple prompts I use to get leaders’ story juices flowing are to think about a time when they:


  • Overcame a significant challenge
  • Came to a fork in the road and made a difficult choice
  • Achieved something great with others
  • Learned something unexpected


The best way to develop a great leadership story is to tell it. Again and again. Practice it. And in the telling, you will undoubtedly discover new depths to it, clarify the real meanings of it, hone it into a stronger, more motivating, connecting story.


How can a manager use their leadership story? Why would they choose to use it? There are many opportunities and many reasons. We don’t have to wait for moments of great inspiration. We don’t have to pull it out only on dramatic occasions like the classic football half-time speech when the team is down by three touchdowns. And we don’t have to be polished storytellers either. On the contrary, you’ll be compelling when you find your own voice and your own comfortable style of telling. And the more practical, less dramatic opportunities to tell your tale happen all the time in the workplace. Here are three common opportunities to share your leadership story with others:


  1. When taking on a new position. The new manager has a great opening window to make an impression, create trust and establish productive relationships with their direct reports. Often the early period is filled with one-on-one meetings as well as multiple team meetings as the new manager does fact-finding and rapport-building while learning their new area of responsibility and establishing priorities. Look to inject stories into these meetings. Help people understand who you are and what motivates you by telling a brief story about yourself or by sharing one of your formative experiences.
  2. When orienting a new report. There is much to talk about with a new employee as we seek to clarify their goals and responsibilities as well as help them understand the resources, tools and processes they need to rely on to accomplish their work. But don’t miss the opportunity to create a personal connection by sharing your story. The number one predictor of job satisfaction for an employee is their relationship with their immediate supervisor. Why not start out on a good, productive personal note that creates rapport and clarifies what’s most important to you. And encourage their stories too. Find out about the unique person who has joined your team and what shaping experiences they have had. They will value your personal interest in them and be more engaged in their work as a result.
  3. When launching a project. Big projects and difficult undertakings often begin with great anxiety. Can we pull it off? Will we be successful? How are we going to accomplish this new thing? Smart leaders use stories to remind their group that teams can accomplish great things together, that they have been part of successes in the past under challenging circumstances, and that they can’t wait to experience success again with this team.


Give stories a try. You’ll find them to be an essential means for expressing your authentic leadership and an invaluable and satisfying way to deepen your bond with the people you lead.

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Jim Laughlin
My passion is helping organizations develop the talent and leadership needed to create sustainable results. I help clients do so at the organizational, team and individual levels, including but not limited to defining future leadership requirements, assessing leadership potential and readiness, building the leadership pipeline at all levels, coaching and developing teams and individuals, succession planning, and change leadership. Clients and colleagues will tell you I am a creative and strategic thinker who is results- and deadline-driven and who also loves forging strong relationships through purposeful work together. As head of MDA’s northeast region, I connect area organizations with MDA’s solutions in leadership development, talent management, assessment, organizational performance, and CEO/board consultancy. For 35 years, MDA has helped large- and mid-sized companies solve their talent issues and get the results they need year after year. I was formerly a Senior Consultant and Director of Product Development for Linkage, Inc., specializing in organizational and leadership development. I led the design, development and delivery of over 60 distinct multi-day training programs and multiple assessments used in Fortune 500 businesses and leading global organizations. I have also held leadership positions in both for profit and nonprofit organizations.