Gwen Webber-McLeod Discusses Legacy, Authenticity, and the Power of the Unexpected Leader

inspiration for the nation

We are thrilled to share the recent, powerful conversation between our CEO, Gwen Webber-McLeod, and George Kilpatrick on his program, “Inspiration for the Nation”. The interview delves deep into purposeful leadership, the importance of legacy, and the unique challenges faced by leaders of color in today’s volatile environment.

Shifting from Resume to Legacy

Gwen Webber-McLeod, the CEO of Gwen Inc. and founder of You Can’t Fail, is known for her commitment to developing leaders, especially leaders of color, across the country. In this interview, she shared that she is now “living in my legacy building years of my career”.

A central theme of the discussion is the urgent question Gwen poses frequently: “What kind of ancestor will we be?”. She emphasizes the necessity of being intentional and clear about the legacy you wish to leave, and putting that legacy into action while you are still alive to see it. When you are clear about your personal mission, vision, and values, your words, deeds, and actions become aligned.

Introducing Your Leadership Journey

This critical conversation comes as Gwen releases her new book, Your Leadership Journey: Living and Leading in and on Purpose. The book is a guide for anyone ready to lead with courage and authenticity, whether on or off the traditional path.

Gwen designed the book, written in “sistership with Susan Besaw”, as a capstone project for her legacy building journey. While anyone can benefit from reading it, she was primarily motivated by the observation that there was a lack of leadership development books specifically designed to help women—particularly Black women—examine and explore their leadership identity, unlike the resources available for well-known male counterparts. The book is also being widely used by executive coaches and mentors across the country.

Gwen explains the meaning behind the title, Living and Leading in and on Purpose:

  • Living in your self-defined purpose requires taking time for reflection to figure out what that purpose is.
  • Leading on purpose means being intentional about your life and ensuring your mission, vision, and values are manifested in visible, evidence-based ways.

Thriving as the Unexpected Leader

Based on her master’s research, Gwen trademarked the term The Unexpected Leader. This describes the phenomenon experienced by Black women, who are often the first, only, and different in their roles. When unexpected leaders go first, they are not shattering a glass ceiling, but literally shattering a cement ceiling. Because they are isolated and no one expects it to be them, they face a career-long struggle to gain and sustain credibility, even when they are often more qualified than their counterparts and consistently exceed expectations. This systemic challenge, rooted in racism, sexism, and microaggressions, is often experienced as impostor treatment rather than impostor syndrome.

Gwen’s book helps these leaders, as well as her Black male clients who often share the same experience, navigate these challenges.

In today’s climate, defined by the military term VUCA (volatile, unpredictable, complex, and ambiguous), Gwen stresses that leaders must anchor themselves in their purpose. She points to high-visibility leaders like Letitia James, Jasmine Crockett, and Maxine Waters as modern examples of unexpected leaders who are frequently subjected to “impostor treatment” and being treated like liabilities instead of assets.

To navigate these turbulent times, Gwen highlights the importance of her Four C’s of Effective Leadership:

  1. Confidence
  2. Competence
  3. Courage
  4. Calm

Gwen shares that her personal strategy for dealing with current challenges, such as the anti-DEI movement which presents an “existential threat”, is to refuse to compromise or co-opt herself. She encourages everyone to remember their history, acknowledging that “we descend from 400 years of people that thrived through moments like this”.

Leading in Every Space

Gwen challenges the stereotype that leadership requires a formal title, asserting that leadership is truly an internal process. She inspires everyone, regardless of their position—from the grassroots leader to the young mom in her neighborhood—to make a conscious decision to be the most important leader in your own life.

Her book is interactive, combining reflections, essays, activities, and worksheets that help readers translate these ideas into action, guiding them to create a leadership development plan for their own non-straight path.


Catch Gwen in Person or Online!

Don’t miss the opportunity to connect with Gwen Webber-McLeod:

  • November 11th: Conversations with The Leadership Diva via Zoom. Register Today!
  • December 4th: Syracuse at the Salt City Market. Register Today!
  • December 11th: Auburn at the Auburn Public Theater. Register Today!
  • December 16th: Conversations with The Leadership Diva via Zoom. Register Today!
  • December 17th: Conversations with The Leadership Diva via Zoom. Register Today!

You can purchase your copy of Your Leadership Journey: Living and Leading in and on Purpose through Amazon, Barnes & Noble, or Claire Songbirds Publishing House.

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