Last week, I found myself exploring the vibrant neighborhoods and beautiful landscapes of Puerto Rico—from the lively streets of Old San Juan and colorful La Perla to the rhythm of bomba at Piñones Beach, the art of Calle Cerra, the energy of La Placita, the innovation of the T-Mobile District, the serenity of Condado Beach and Luquillo Beach, and the lush rainforest of El Yunque—reflecting on how journeys often take unexpected but profoundly meaningful turns.

Originally, I had planned to travel to Puerto Rico to interview as a semi-finalist for the presidency of the University of Puerto Rico (UPR)—an incredible institution with a historic legacy of academic excellence and cultural leadership. It would have been an absolute honor to serve as the next president of UPR, guiding its future at a critical time for higher education on the island and beyond.

However, the logistics of the interview process posed real barriers. The requirement to conduct 11 separate interviews across campuses located across Puerto Rico over a three-week period, without logistical or financial support from the search, proved to be too difficult to navigate while honoring my other professional obligations. Due to this, despite my deep enthusiasm, I ultimately had to withdraw from the search and step back from the amazing opportunity.

But sometimes, when one door closes, another meaningful one opens.

Through a fortuitous invitation from my friend and former NEA Foundation board colleague Pedro DeJesús, I was able to keep my visit to Puerto Rico to attend the Latino Leaders Magazine C-Suite & Board Directors Forum at the elegant Condado Vanderbilt Hotel on April 23, 2025.

What unfolded over those few days was nothing short of inspiring.

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A Gathering of Purpose-Driven Leaders

The C-Suite & Board Directors Forum brought together top executives, board directors, and rising leaders from across Puerto Rico and the mainland U.S. for a day of powerful conversations about leadership, governance, innovation, and diversity. It was a space for Latino excellence to be celebrated—and strategized.

The agenda featured dynamic sessions on:

• Executive presence and personal branding
• Private company governance and the future of corporate boards
• AI innovation strategies for business and leadership
• Enduring board effectiveness and sustainable organizational impact
• The personal journeys of top CEOs from Puerto Rico

Pedro DeJesús himself (pictured center below)—serving as Head of International Business and EVP, General Counsel & Corporate Secretary at Tampico Beverages—offered powerful insights during a panel on effective board leadership, drawing on his vast experience navigating corporate governance across diverse sectors.

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Leadership Lessons Across Sectors

One of the most profound experiences during my trip happened the evening after the forum. I had the privilege of attending a private dinner hosted at the historic Caribe Hilton, sponsored by KPMG and the Latino Corporate Directors Association (LCDA).

Gathering with corporate leaders, board members, and organizational changemakers around the table offered a different but deeply resonant perspective on leadership.

One particularly striking insight that emerged from the dinner conversation was this:

Boards should be comprised of people who are prepared to take the organization to where it needs to be—not where it has been.

That reflection stuck with me.

It immediately reminded me of the discussions I’ve had in educational leadership circles—from school boards to university trustee committees. In education, too often we see leadership bodies stacked with individuals chosen for their historical ties or political alliances, not for their vision of where institutions need to go.

True leadership requires forward-looking courage, not backward-looking comfort. Whether in education or in corporate governance, it’s not about preserving the past—it’s about building the future.

The parallels between corporate leadership and educational governance were clearer than ever:

• Both require diversity of thought and experience to stay relevant.
• Both demand board members who understand not just fiduciary responsibility but social responsibility.
• And both are at critical inflection points in this era of rapid social, political, and technological change.

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Gratitude for the Journey

Although my original purpose for coming to Puerto Rico shifted, I’m deeply grateful that this journey became a different kind of renewal—an opportunity to connect, to learn, and to expand the ways I think about leadership, service, and institutional stewardship.

I left Puerto Rico inspired by the leaders I met and energized by the important work ahead—whether in public education, nonprofit boards, corporate governance, or broader social justice spaces.

Special thanks to Pedro DeJesús for the invitation to the forum, to Latino Leaders Magazine for curating such a rich and affirming event, and to the organizers of the KPMG/LCDA dinner for hosting a space of authenticity, honesty, and forward vision.

While I was not able to continue interviewing as a semi-finalist for the presidency of the University of Puerto Rico, I left the island with something equally powerful: a renewed commitment to lead with vision, purpose, and the determination to help every institution I touch grow not just into what it has been—but into what it needs to become.

Because real leadership isn’t nostalgic.
It’s transformational.

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Stay tuned for more reflections from the frontlines of leadership and educational justice here at Cloaking Inequity. Please share.
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