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Wes Moore: Lessons in Leadership

Wes Moore has led a life that has taken him from warzones to the executive suite. He reflects on his path to the Maryland gubernatorial race on this week’s “Out of Office.”

Click here to listen to the full episode.

When Wes Moore was four years old, he watched his father die. Having been denied proper healthcare, his young father returned home, only to collapse a few days and leave his wife alone with three young children. Despite being so young at the time, the memory remains vivid for the 43-year-old Moore.

Unsurprisingly, the pivotal moment shaped the course of Moore’s life thereafter. After spending his earliest years as a fourth-generation Maryland resident through his father’s side of the family, his mother moved Wes and his sisters north to the Bronx, where she’d spent her own formative years. She searched for solace, but her vibrant, smart, and vivacious son had plans to keep her on her toes.

As Moore looks back on his journey through the ups and downs of his education and his career, he points to one repetitive lesson arc that set him on the path to where he is today: the importance of leadership. The way that he metabolized those lessons took him from the military school to the top spot at one of New York City’s most impactful nonprofits. He reflects on it all and the lessons he’s learned on this week’s episode of Boardroom’s “Out of Office” podcast with Rich Kleiman and Gianni Harrell.

When Wes was 14, Moore was sent away to military school. He had been enrolled in the elite Riverdale Country School — which boasts famous alumni ranging all the way from John F. Kennedy to Tracee Ellis Ross — but he struggled to stay out of trouble both at home in the Bronx and in the school’s hallowed halls.

“So, respectfully, [did] they kick your ass out of Riverdale and say, ‘Go get it together?'” Rich asked with a laugh.

“Respectfully, yes,” Moore is quick to answer.

Years later, when he was serving as the CEO of the Robin Hood Foundation, Moore was invited back to the campus to give a speech and received an honorary degree, which hangs proudly in his mother’s home to this day. When the head of school took him out, he asked Moore what could have been different to make him succeed. After thinking on the question for a moment, he responded, “I wish they had talked to me, not about me.”

For Moore, this early observation stuck. As he has navigated various challenges and opportunities in his own life, he adopted a desire to listen deeply and profoundly to the people with and for whom he was working as a core ethos of his approach to leadership.

Wes Moore at the opening of his gubernatorial campaign office in Prince George’s County, Maryland (Brian Stukes/Getty Images)

On his first day in the docks at military school, Moore recalls trying to sidestep the 5:30 a.m. wakeup (assisted by the blaring sounds of Guns ‘N Roses) by throwing his pillow over his head and asking for a later alarm. Quickly, he learned that the rules served a more profound purpose than he first thought, and that his responsibility to his squad was much greater than his desire for a few more minutes of shuteye.

While he is not so revisionist in his storytelling to characterize his time at the school as a cakewalk, he’s grateful for the lessons that he learned, specifically about leadership. “There was this graduated sense of responsibility,” Moore recalls. He felt a sense of accountability and was introduced to leadership responsibilities in a compounding way, which he credits with forming his skills as they are today.

Plus, he learned to communicate, both to his squad and to his superiors, generating a sense of personal and collective responsibility that promised to unlock success.

Fast forward years later, and it was this same sense of accountability to his squad — and his country — that led Moore to leave a cushy career where he was jointly pursuing a doctorate at Oxford and to enlist and deploy to Afghanistan. He told those around him that he was “drafted,” but the reality is that he submitted a by-name request in order to fulfill his sense of commitment.

He returned from combat to resume a version of the life he had left behind. While he sat in boardrooms throughout the day, he also wrote a book about a man who had the very same name as himself — The Other Wes Moore — but followed a very different life path that landed him in Jessup Correctional Institution, just 30 miles from where Moore lived at the time. The experience of examining their lives in tandem led him to adopt a more sophisticated understanding of people, more generally.

“We’re very quick to either congratulate or to castigate. And we don’t yet even fully understand the backgrounds of what we’re talking about.”

Wes Moore speaks onstage during the Robin Hood Benefit 2019 at New York’s Javits Center, 2019 (Kevin Mazur/Getty Images for Robin Hood Foundation)

This deep curiosity in people led him to the Robin Hood Foundation, which has the sweeping mission to elevate New Yorkers out of poverty.

The job — “the CEO of Disney,” as Rich joked — was complex. He worked with and for everyone, from the clients that the foundation served to the top-level donors. He routinely sought out opportunities to connect with people and provide a diverse population with a seat at the table, bringing them into the design process.

But after four years, he realized his journey’s next stop was a career in politics, one that offers a chance to effect change on an even more profound sort of scale.

He sees similarities in the life of a politician to all of the careers that he has previously held. “I don’t think that progress is partisan,” he says. “I think that when it comes to being a chief executive, like the thing that you have to be committed to is the people.”

With the gubernatorial race in full swing, he’s got his eye on the governor’s mansion as the next stop in a lifetime of leadership.

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