How to Share Your Leadership Story and Leave a Legacy with Shelley Goldstein

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The epitome of leadership is the ability to share your leadership story and leave a legacy. I discuss how to do that with my guest, Shelley Goldstein.

Shelley Goldstein is a leadership development coach specializing in communications affectionately known by clients as “The Coach Whisperer”. The moniker stems from her intuitive ability to pinpoint untapped potential in leaders and cultivate it into speaking mastery with remarkable ease and speed.

As the architect of Remarkable Speaking, Shelley has created a proprietary framework that has evolved into a global leadership development platform. Rooted in 30-plus years of experience in leadership, entrepreneurship, marketing, and design, her expertise allows her to creatively integrate time-saving drills, persuasive storytelling, and behavioral psychology, driving significant real-world impact.

Your Leadership Story

Your leadership story begins with the origins of why and how we do things. It can go back to your youth when you’re joining a music program or getting involved in sports. It’s a study of behaviors involved with those activities. It’s those stories that build one on top of the other that become your legacy, who you are today, and why you lead the way you do when situations call or leadership.

Shelley’s Leadership Story: Back to the Beginning

Shelley says her story goes back to when she was eight or nine years old and her and a group her friends put together a neighborhood newspaper. The three of them were about the same age. They included hosted a beauty pageant and had articles and recipes that they got from their neighbors. Being able to organize that at such a young age and publish it month after month had a profound impact on leadership in Shelley’s adult life.

Looking back, she learned a lot about leadership skills and taking the initiative at a very young age. Some of the things she carries forward with her today is the idea of sharing that responsibility and delegating to other people. Whether she was aware of it or not, it just naturally happened. And Shelley believes that’s what helps her be a better leader today; that sharing of ideas and giving people autonomy to create some of the most innovative, creative ideas of their childhoods.

Leadership Showing Up

Shelley remembers her earlier career as a costume designer. She had the responsibility of creating a look, making sure the costumes could be perceived from the audience. That meant meaning when that curtain goes up, she can’t be up there with the assistants hemming and sewing. It was showtime. Shelley believes that whole idea of “it’s showtime” was an early leadership development experience in her adult life. She realized that she can’t do everything.

She had to prioritize and realized you can’t sweat the small stuff. To lead through that and make sure her team understood that the work that they were doing as individuals contributed to their combined success; and that bigger vision of what things need to happen.

The Beginning of Leadership in Your Adult Life

It’s so hard to say where it actually begins.

If you have an idea, let’s start with the incubating. You have a great idea. How you strategize that, how you move forward with that, that’s an innate leadership skill. I’m going to have a marketing strategy. I’m going to have a sales strategy. I’m going to develop my brand this way. Those are all leadership skills because you’re making important decisions. Those stories of how you eventually do that, that becomes the legacy. That becomes your competitive advantage and unique story to only you.

The stories are so important because that’s where the money flows. Money is how people respond to the stories. That’s what people buy into. That’s the journey.

The Structure of a Great Leadership Story

A great leadership story is the journey, the mistakes, the decisions you made when you were building your business. You know what? I’m going to go with my marketing strategy and hire this team and go forward with them. And let’s say it’s a bomb. Nothing happened. Six months, you spent thousands of dollars. That’s a learning moment. So, what did you do to compensate for that, to switch gears and become the success you are today?

It’s the little things that we think are so unimportant. For example, Shelley coached a young guy who was a very successful entrepreneur. He made well over a hundred million dollars in his twenties. He was a college dropout, and he created a watch company.

He built his company and sold the organization for hundreds of millions of dollars. After the company’s sale, he came to Shelley and said, “I have nothing to talk about. The company sold and that was my identity. I don’t know what to talk about and how to show up now. Who am I? I’m nothing without that organization.”

What they unpacked together was the fact that that journey, whether it’s in the past or it’s current, is part of that story, is part of that legacy. Identifying with that as an entrepreneur and focusing in on the little moments, the pivotal moments, the early days where you had no followers, let’s say, to the time where you had millions of followers, to the time where you couldn’t fulfill your first order for your product, to the time where you sold hundreds of millions of units. All those details are every bit of who you are today and where you’re going tomorrow.

And changing that story and being able to express that story changed everything for this young entrepreneur. He’s now running a lot of other businesses based on that experience because that’s what people want to know and that’s what they’re buying into.

We also dive into topics including:

Why it’s important to create and share your genesis, or origin story with the world.
The failures as well as the successes, the nuanced moments when you felt that it was over; that’s what inspires people.
Why superheroes are great examples of origin stories; they share their weaknesses, vulnerabilities, and failures with the comic world. You should in your world too.
How to keep on keepin’ on during the dark times in your life.
The importance of creating and following a vision for your business and how to do it.
When to hold the course and when to change directions in life.
Where the growth and change happen along your journey and how to embrace them.
The definition of “legacy” and how and when to create yours.
How to move your audience forward by sharing your legacy.
Why and how “the money flows as an extension of your story”.
How to get people to buy into your legacy.
The importance of vulnerability and humbleness in leadership.
Why you need to have an open-door policy with your team for sharing ideas and feedback.
How to create a safe environment for tough conversations.
How to get the people around you to embrace and share their legacy.
The one thing, above all else, you need to do to share your leadership story and leave a legacy.

…and other golden nuggets of advice!

You can get my book here: “Idea Climbing: How to Create a Support System for Your Next Big Idea”

About My Guest

Shelley Goldstein is a leadership development coach specializing in communications affectionately known by clients as “The Coach Whisperer”. The moniker stems from her intuitive ability to pinpoint untapped potential in leaders and cultivate it into speaking mastery with remarkable ease and speed.

Through a fusion of her multicultural experience and multidisciplinary approach, Shelley has personally coached over 1,000 C- and V-suite executives, senior officers and managers, and has led more than 150 cohorts worldwide. Her extensive work spans a diverse array of industries, with a particular focus on the technology, financial, legal, and manufacturing sectors.

The Remarkable Speaking brand speaks for itself; empowering high-achieving leaders and visionaries with the directness, clarity, and composure essential to command authority and truly influence individuals and industries.

Connect with Shelley on LinkedIn!

Check out Shelley’s Book!

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