The Board That Got It Right: How Aligned Leadership Can Accelerate Mission

When I first heard Derrick Chubbs speak at a conference earlier this year in Florida, I was instantly drawn in. You know when someone just has it? That mix of poise, humor, and authenticity that makes you sit up and think, “Okay — I need to know more about this person.” Derrick was that.

He was well-spoken, personable, accomplished, and relatable all at once — the kind of leader who makes you believe in the power of calm confidence. And as I listened, I realized something: Derrick has the secret sauce so many leaders spend years searching for — a board that actually supports him. It’s no surprise then that Orlando Magazine named him as one of the “50 Most Powerful People in Orlando,” topping the list of Philanthropy and Community Voices.

A Story Rooted in Purpose

Derrick’s journey isn’t the kind you find in a textbook. He was adopted — an experience that shaped his empathy and purpose from an early age. He’ll tell you that being given a chance made him want to spend his life opening doors for others.

He earned his bachelor’s degree from Georgia State University and later his MPA from the University of Texas Rio Grande Valley. Before accepting his current role as President & CEO of Second Harvest Food Bank of Central Florida — which serves seven counties across Central Florida — he served as CEO of the Central Texas Food Bank.

These days, when he’s not feeding communities, you might find him relaxing on a golf course — his favorite way to clear his mind and recharge.

At Second Harvest, the impact is staggering — 300,000 meals a day, 98 million pounds of food distributed last year. But what stood out most was the way Derrick talked about the people behind the numbers — the team, the partners, and especially the board that makes it all possible.

A Board That Gets It

Here’s what makes Derrick’s board exceptional: they don’t just show up — they step up.

They bring expertise, networks, and strategy to the table — not to micromanage, but to multiply impact. With 100% board giving, they send a clear message: we’re not just invested — we’re all in.

And importantly, they take strategic board recruitment seriously — making sure the right voices, expertise, and lived experiences are always at the table.

They ask smart questions. They connect the dots between funding and long-term sustainability. They show up when it’s hard, not just when it’s convenient. And above all — they’ve built something that can’t be faked: trust.

Derrick and his Board Chair have what every CEO dreams of — open communication, shared accountability, and genuine partnership. They talk often, not only when there’s a crisis. They plan, reflect, and celebrate together. That rhythm shapes the culture across the organization.

The Real Lesson

As someone who has worked with hundreds of boards, I can tell you — this doesn’t happen by accident. It takes time. Intention. Humility.

And Derrick leads with all three.

He’s proof that when a board and CEO move in harmony, magic happens. The mission gets clearer. The strategy gets stronger. People get fed — literally and figuratively. At the end of the day, Second Harvest isn’t just feeding families. They’re feeding hope. And that hope starts in the boardroom.

Because when the board leads with vision — and the CEO leads with trust — everybody eats.

Boards, Take Note.

What Derrick and his board have built isn’t luck — it’s culture. It’s clarity. It’s courage. It’s the result of a board that understands its role isn’t to hover or disappear — it’s to partner.

If your board isn’t pushing strategy forward…If your CEO is carrying the mission alone…If your meetings feel more like reporting than reimagining…

— then it’s time to pause and reset.

Because boards don’t just protect missions. The best ones accelerate them. And when the board believes, gives, recruits strategically — and shows up like it matters — the entire organization rises.

Written by Christal M. Cherry, The Board Pro — on a mission to build boardrooms where everyone feels seen, valued, and empowered to lead.