Exit Planning

Defining your leadership legacy

leadership legacy

As a leader, how do you want to be remembered?

What lasting impact do you want to have on your employees, business, and community?

What will be your leadership legacy? 

Vistage Chairs Phillip Thomas and Michael Flannery talk about why legacies matter and how to craft yours. They also explain how executive coaching offers an opportunity to leave an ongoing, positive impression.


Why your leadership legacy matters

Flannery shares that he has spoken with many leaders who have regrets about the influence they left. In one case, Flannery’s close friend and CEO of a large construction company had a life-changing experience that motivated him to reflect deeply on his life.

“He had the chance to apologize to some of his employees but unfortunately was not able to reconcile with everyone,” says Flannery, “this was very disappointing to him.”

Leaders at every level will one day look back on their leadership legacy. None one wants to be tormented by how they treated people.

“There’s going to be a day when you’re going to reflect back on your career. You’re going to reflect back on the impact you’ve had on others. How do you want to feel about that?”

Thomas has been thinking about his impression for a long time. He founded a company, Legacy Ventures, based on leaving behind what he calls “a noble legacy.” Some of the company’s pursuits included breast cancer treatment and improving patients’ access to medicine.

“As a CEO, you’re going to leave some sort of legacy behind — good, bad, or indifferent,” he says. “You may as well associate yourself with noble causes and things that have scope and dimension to it that are going to help a lot of people. Not just focusing on the money.”

3 steps to crafting a leadership legacy that lasts

Maybe you want to start thinking about your ongoing influence, but you’re not sure where to start. Fortunately, there are some simple steps you can take to start building your legacy.

And no matter where you are in your leadership journey, you can begin following these tips today.

“You don’t have to think about this as a retirement thought,” says Flannery. “From a leadership perspective, are there things that you want to imprint on your current managers or directors that you could start today and see the results in one year, two years, three years down the road?”

1. Understand your values and vision

One essential step in crafting a legacy is to ensure your impact aligns with your values and vision. When you seek clarity regarding your purpose, your team understands it better and can help work towards applying your beliefs.

Don’t assume everyone knows what your vision is. Instead, make it clear on an ongoing basis.

Thomas says that one company he’s worked with has its core values posted on the wall in the conference room, where workers see them every day. Another company assigns an employee to talk about one of the business’s key principles and what it means to them for five minutes during each staff meeting.

One value Thomas subscribes to is creating a “mutually supportive” environment, where people come to work because they love what they do, as opposed to a “dog-eat-dog” atmosphere.

2. Build lasting relationships

Your work environment can help you create your ideal legacy. A happy, healthy environment enables you to do your best work; it’s also a reflection of the impact you’re moving toward.

If your employees are able to thrive, they’ll be more motivated to carry on your influence after you leave.

Aim for positivity, accountability, and a sense of trust that goes both ways between you and your employees.

Flannery references “The Leader’s Guide to Radical Management” by Steve Denning. One lesson Flannery applies from the book is to ensure employees have a direct line of sight into how they’re making a difference. This direct line leads to a higher level of engagement and satisfaction.

“People really want to know how they matter,” he says. “They want to know that they’re more than just somebody sitting in a seat that gets a paycheck every couple of weeks.”

3. Determine your unique offering

You have distinctive skills, talents and viewpoints. Part of leaving a lasting legacy is using these qualities to the best of your ability. As you do so, you’ll stand out from the crowd and make a difference in your business and community.

Perhaps you’re a fantastic public speaker. Part of your legacy could be speaking to audiences about important topics related to your values. If you’re a great writer, you could build a library of educational materials. Or, you could write a book that will help readers long after you’re gone.

The goal is to consider what you can offer that no one else can. If you have trouble identifying your special attributes (or how to use them), a coach can help.

Executive coaching: a lasting impact

An encore career as an executive coach can give you a new opportunity to build your legacy.

“One thing that drew me to Vistage was the nobility of the role,” says Thomas, for whom nobility is a core value. As a coach, he says, “You’re leaving a legacy of growth and development, and hopefully better products, better services and just a better world. Think of it in that context, and you will love this job.”

Thomas mentions Vistage CEO Sam Reese as an example of a positive legacy. As Thomas puts it, Reese’s impact is helping thousands of businesses and leaders be better. This creates a domino effect that leads to helping each company’s entire community.

Flannery’s work as a peer advisory group facilitator gives him the opportunity to “help CEOs achieve their visions.” Part of a coach’s legacy is to guide other leaders as they decide how they want to be remembered.


Related Resources

3 steps for starting an encore career

Rethinking the ‘Second Mountain’

Category : Exit Planning

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About the Author: Vistage Staff

Vistage facilitates confidential peer advisory groups for CEOs and other senior leaders, focusing on solving challenges, accelerating growth and improving business performance. Over 45,000 high-caliber execu

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