A Legacy of Leadership

Gwendolyn Webber-McLeod, the leading lady behind Gwen, Inc., is paving the way for women of color to lean into living in and on their purpose

By Courtney Rae Kasper / Photography by Kimberly Cook

1113 cover 1 bkgd fix edit  DSC_4586She is kind. She is smart. She is very important.

She is Gwendolyn Webber-McLeod, president and chief executive officer of Gwen, Inc.

With nearly 30 years of experience under her stilettos, Webber-McLeod has become a nationally sought-after mentor, coach and speaker in the field of leadership development. In her company’s capacity, she and her team of consultants serve as a support system to high-power executives, mid-level managers, leadership teams and anyone who identifies as a leader to help them develop the philosophies, skills and behaviors of effective leadership, or what she has termed as becoming confident, competent, courageous and calm leaders.

1113 cover story edit  DSC_4659 grainyPresently in the legacy-building stages of her career, Webber-McLeod, 57, has made it her life’s work to ensure that professional and young women of color, who she said are oftentimes viewed as society’s most unexpected leaders, will succeed in carrying on her mission. “I’ve always stood as a leader in that intersection of race and gender,” she said. “I’m intentionally conscious about being successful, doing a good job and inspiring other women of color to see entrepreneurship as a way for them. While it’s an honor to be the first and only in something, dealing with the isolation that can come with the ongoing stress of constantly needing to prove that you’re good enough, smart enough and talented enough and looking behind you to see that young women who look like you are watching you is a lot of pressure to be under. Women of my generation have a real opportunity to speak our truth in ways that I hope will make it easier for younger generations to live their lives.”

Webber-McLeod’s rallying cry for other women of color: failure is not an option. Why? Because history says you can’t. This has become the motto for her annual event, You Can’t Fail. Now in its fifth year this month, Webber McLeod’s one-of-a-kind conference acts as a “safe haven and soft landing” space for women of color and those who support them. And due to popular demand, she is happy to announce that YCF will soon expand to encompass more leadership education in the form of regular workshops, group and individual coaching and other gatherings across the state specifically designed for professional women of color.

But perhaps the most exciting adjustment made to the upcoming event, You Can’t Fail: In Her Footsteps, is showcasing local rather than national speakers during this year’s panel, Leaning In From a Sister’s Point of View, which will celebrate Sheryl Sandberg’s empowering, Lean In: Women, Work, and the Will to Lead, and the 100th anniversary of Harriet Tubman’s death — two women who Webber-McLeod truly believes are historical sisters when it comes to making a difference in women’s lives today. “My mother was probably ahead of her time because she raised a bunch of leaned-in daughters. We just didn’t call it being leaned in, so when I started hearing about and reading Sheryl Sandberg’s book, it really aligned with what I’ve always believed since I was a little girl,” said Webber-McLeod, who makes up one fourth of the iconic Webber girls of Watertown.

With this dialogue being reopened in the 21st century, the self-proclaimed feminist knew it had to be the centerpiece for this year’s conference. “I really wanted to spark that conversation with some very high level and emerging women of color to let us have the conversation where it’s just us,” she said, adding that the panelists chosen include Michele Jones Galvin, Nasha Barnes, Jackie Robinson and Sharon Contreras. “I am taken with how these women see leadership as a function of who they are and what they believe. They share a core message that a woman’s success is tied directly to her capacity to believe in herself and her dreams.”

1113 cover story DSC_4625 not cover-BWebber-McLeod began navigating her own journey into leadership fresh out of college, having been recruited to take a position as a community educator for Planned Parenthood in Auburn. It wasn’t long after that the then 25 year old became the executive director of the iconic Booker T. Washington Community Center and later served in the same role at the National Women’s Hall of Fame in Seneca Falls. It was in these first few roles where she began to understand the technical difference between just being a manager and being a leader. “I truly believe that leadership is a matter of the head, the heart and the gut,” she said. “I think way too many leaders only live in their head. People aren’t following your job title; they’re following you, so who you are has to be something that feels authentic and matches your capacity to deliver results.”

By 2008, Webber-McLeod’s interest in what happens in the life of a leader transpired into the formation of her namesake incorporation, thus giving her the unique position to speak up. “We come from legacies of women, generations of them, who have stood in the worst conditions and been successful. We need to check ourselves and ask, what is going on with us? And what is going on with us is something that resides as an unspoken in most organizations or companies, and I’m uniquely positioned to say it out loud,” she said.

But Webber-McLeod will be the first to admit that it took a long 10 years to muster up the courage to make her own dream a reality. “I was raised to believe that it was my birthright to explore anything that I wanted to explore,” she said, recalling a poignant childhood moment when her mother, Barbara Webber, gave her the aspirational vision that she could be an astronaut if she wanted to. “I think that often women leaders confuse feeling powerful beyond measure with being afraid that they can’t do something. For me, sifting out what I was feeling was really the thing that cleared the path for me to do it. There was never a moment in my mind that I didn’t think that I could make this happen.” The major push was part of a grief management strategy to overcome the many hardships experienced during the start up years of her business, from her daughter’s cancer scare to her father’s death to the too-soon fatalities of several friends and her younger sister. “I’m either going to crawl to the bottom of my bed, or I’m going to lead my way out of this by doing what I think I was put on this planet to do,” she recalled.

Her next challenge was getting high level leaders to admit that they needed the support she was offering, which she approached through penning a column titled “The Leadership Journey” for The Citizen. “My willingness to humanize the profession through my writing gave people the courage to contact me, and over time, I built a tribe of followers,” she said. Still to this day the majority of Gwen, Inc. clients find Webber-McLeod via word of mouth.

A graduate of SUNY Potsdam University and Keuka College, where she earned a master’s in management, Webber-McLeod, the daughter of the late Lieutenant Colonel Charles Webber, has garnered a laundry list of awards, accolades and other civic notorieties, including the Women Who Mean Business Award and The New York State Senate Woman of Distinction Award. Yet she remains humble in her ability to never allow others to view her as a celebrity figure, or what she calls the veneer of leadership.

She credits her children, Ashley, 28, and Travis, 24, and her husband of 30 years, Tracy McLeod, as her rock and number one supporters, along with her team, who help keep the mentality of “don’t talk about it; be about it” in check. “We’ve all had moments where we’re like really, I could be at home in my pajamas eating bonbons instead of enduring this crap on a daily basis, but my husband will say to me, ‘girl, get up and get in your car and go to that meeting because don’t you ever forget about that little tiny woman walked herself from Maryland to Canada and wound up in Auburn, New York, because she believed in something. You believe in what you’re doing, so get up and go!’” she shared.

While Webber-McLeod is aware that she could be making more when it comes to signing her own paychecks, she prides cautious business strategies over monetary gain to ensure that integrity and ethical behavior always remain intact. “When I realize that every single time my company helps a leader increase their own effectiveness, we’re truly impacting generations of people because of the magnitude of the decisions these people have to make as leaders. That’s the stuff that takes my breath away,” she said. “It’s a beautiful thing to literally be in and on my purpose everyday and get paid to do it. I’m just being brave.”

1113 cover story edit DSC_4570Plus, she’s a firm believer that she has some rather courageous shoes to fill, as it isn’t by accident that she found herself claiming feminism as part of her philosophy, studying women’s history and eventually settling into the same community, much less residing directly between the former home and current resting place of the woman she most admires — Harriet Tubman. “I don’t think it’s by chance that I’m doing the work that I’m doing as a black woman leader and was attracted to this community as I’m starting to find my leadership,” she said. “I really do believe it’s because I’m following in Harriet’s footsteps. I feel very obligated to her.”

Posted in plain view from the desk in Webber-McLeod’s home office is a magazine tear out of “Good Morning America” host and ESPN’s first on-air African American anchorwoman, Robin Roberts; mementos of her Delta Sigma Theta Sorority, the largest African-American Greek-lettered organization founded 100 years ago by collegiate women with big dreams for social change; and a poster-size print of the three-line inspirational quote made famous in Kathryn Stockett’s breakout novel, written to depict strength through sisterhood in the segregated South, along with a window that constantly resonates a picture perfect view of her significant geographical location between the final dwellings of one of history’s most leaned in women — all daily reminders that this is not a pinch-me moment, this is her real life, a life she was born to lead because her history continues to tell her that she can.

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Courtney Kasper

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