The Edge of Tomorrow

Where Brave Leaders Shape Bold Futures

May 13-15, 2026 | Hilton Miami Aventura, Florida

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THE #1 Caribbean Leadership Event in the World

Honouring Our Roots, Building Bold Futures

Caribbean leaders have always stood tall in the face of change: resilient, adaptable, and rooted in community.

This is where that legacy meets the future. Step into a space built for leaders who dare to disrupt, innovate, and shape what comes next.

A Personal Message from the Founder

When I launched the Disruptive Leadership Conference in 2019, I had a simple but powerful idea: to create a space where Caribbean leaders could come together to think differently, challenge assumptions, and engage in honest conversations about the future of leadership.

At the time, there were many conferences about leadership, but very few spaces where leaders could openly discuss the complexity of the world we are navigating — the rapid pace of change, the uncertainty facing organisations, and the responsibility leaders carry when shaping the future of people, institutions, and our region.

What began as a bold idea quickly became something far more meaningful.

 

Over the years, the Disruptive Leadership Conference has brought together extraordinary voices — CEOs, innovators, policymakers, academics, entrepreneurs, and emerging leaders — all united by a shared belief that leadership must evolve if our organisations and societies are to thrive.

Together, we have explored difficult questions, challenged traditional thinking, and created a community of leaders who are not afraid to rethink what leadership can look like in the Caribbean and beyond.

This year’s conference is particularly meaningful for me.

As the founder, I am deeply grateful to every speaker who has shared their wisdom, every partner who believed in the vision, and every participant who invested their time and energy in these conversations. Your support has helped shape this conference into a space of insight, courage, and connection.

Leadership, at its core, is about creating spaces where people can grow, ideas can challenge us, and new possibilities can emerge.

That has always been the spirit of the Disruptive Leadership Conference.

While this year marks the final edition of the conference in its current format, I believe deeply that the conversations we have started here will continue — in boardrooms, in organisations, and in the courageous decisions leaders make every day.

Thank you for being part of this journey.

And thank you for believing, as I do, that the future belongs to leaders who are bold enough to shape it.

With gratitude,

Judy McCutcheon Founder, Disruptive Leadership Conference

You’re a Caribbean Leader.

This is Your Space.

You don’t need a title to lead. But the Disruptive Leadership Conference attracts those serious about shaping the future:

Brave Leaders
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Diverse voices from around the world.

Transformational Days
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Immersive learning and connection.

Bold Guides
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Visionary speakers and facilitators.

Everything You Need to Lead at the Edge & Be Ready for What’s Next

Step into a space designed for Caribbean leaders to sharpen their edge, expand their vision, and shape bold futures.

Future-Ready Strategies

Navigate rapid change with confidence and clarity.

Courageous Insights

Learn from leaders who’ve faced hard choices and won.

Powerful Connections

Build a trusted network across the Caribbean and beyond.

Practical Tools

Walk away with frameworks you can use immediately.

Rooted in the Caribbean.

Ready for the World.

The Disruptive Leadership Conference is more than an event. It’s a meeting of Caribbean minds who know what it takes to thrive despite the odds.

Here, you’ll engage in conversations and build connections that help you balance proven practices with bold innovation, turning challenges into opportunities to lead smarter.

2 Transformational Days That Will Shift Your Perspective

In just two days, you’ll learn from global and Caribbean thought leaders, gain tools to lead with confidence, and build connections that expand your influence. This isn’t preparation for the future… it’s ownership of it.

2026

2026 Speaker Lineup

We’re curating an unforgettable program of keynote speakers, panelists, and workshop leaders for 2026.

Additional speakers will be added soon – stay tuned!

hosted by

Dr. Terri-Karelle Johnson

Dr. Terri-Karelle Johnson, an award-winning media professional, international speaker, and author of My Brand Compass, returns for her seventh consecutive year as host of the Disruptive Leadership Conference. Recognized on MIPAD’s 2023 Global Top 100 Under 40 list, she is widely admired for her commanding presence, compelling storytelling, and unmistakable professionalism.

We’re delighted to have her back on stage, bringing her signature spark once again.

Moderators:

Aka Ali-Kerr

Marlon Hill

Here's a quick look at the

CONFERENCE SCHEDULE

Welcome

  • Evening Cocktail Reception
    Evening Cocktail Reception 7:00 PM – 10:00 PM

    Join speakers, partners, and fellow attendees for an evening of connection and conversation as we kick off the conference experience.

Exploring the Edge of Leadership

  • Registration and Morning Coffee 8:00 – 8:30 AM
  • Welcome, Opening Remarks, Housekeeping and Setting the Stage 8:30 – 9:00 AM
  • Conference Opening Address
    Conference Opening Address 9:00 – 9:45 AM

    Fearless Leadership: Making Bold Decisions in Uncertain Times: A powerful opening address examining the courage required to lead in an era defined by uncertainty, disruption, and rapid change. with Judy McCutcheon

  • Leadership Forum 9:45 – 10:30 AM

    Data, Digital, and Disruption: Redefining Strategy for the 21st Century: An exploration of how emerging technologies, digital transformation, and data-driven decision-making are reshaping leadership and strategy. with Rawati Heeraman, Duran Humes, Kareem Williams

  • Connection Break 10:30 – 10:45 AM

    Take a pause to connect, explore new ideas, and continue building meaningful relationships.

  • Fireside Conversation
    Fireside Conversation 10:45 – 11:25 AM

    The Leader’s Inner Game: Healing, Self-Awareness, and Legacy: A reflective conversation on the inner work of leadership and how personal growth shapes leadership impact. with Johnathan Johannes

Choose ONE of the following interactive sessions:

  • Leadership Lab 1
    Leadership Lab 1 11:25 AM – 12:25 PM

    Unlocking Potential: How Leaders Coach for Performance and Growth
    with Aka Ali-Kerr

  • Leadership Lab 2
    Leadership Lab 2 11:25 AM – 12:25 PM

    Design Thinking for Everyday Leadership
    with Dr. Rochelle Haynes

  • Networking Lunch 12:25 – 1:55 PM
  • Fireside Conversation
    Fireside Conversation 1:55 – 2:35 PM

    The CEO’s Dilemma: Balancing Profit, People, and Planet
    A candid discussion on navigating the competing pressures leaders face while building sustainable organizations.
    with Larry Lawrence

  • Leadership Forum 2:35 – 3:20 PM

    Women at the Edge: Bold Leadership for Bold Futures
    A dynamic conversation exploring how women leaders are shaping the future through courage, innovation, and influence.
    with Alison Browne Ellis, Stacey Liburd, Audrey Joachim, Ingrid Murray

  • Day One Closing Address 3:20 – 4:05 PM

    From Fragile to Resilient: Building Organisations That Thrive Amid Disruption
    An inspiring closing session on how leaders can build resilient organizations capable of thriving in uncertain environments.
    (Speaker TBA)

Shaping Bold Futures

  • Morning Coffee 8:30 – 8:45 AM
  • Reflections from Day One and Opening of Day Two 8:45 – 9:00 AM
  • Opening Keynote
    Opening Keynote 9:00 – 9:45 AM

    Leading on the Edge: Reimagining Leadership in the Age of AI:
    An exploration of how artificial intelligence and emerging technologies are transforming leadership and the future of work.
    with Cliff Worley

  • Leadership Forum 9:45 – 10:30 AM

    Caribbean Leadership on the Global Stage: Amplifying Our Voice:
    An exploration of how emerging technologies, digital transformation, and data-driven decision-making are reshaping leadership and strategy.
    with Melissa Noel,Amad Rashad Thompson, Yvette Noel-Schure

  • Connection Break 10:30 – 10:45 AM

    Take a pause to connect, explore new ideas, and continue building meaningful relationships.

  • Fireside Conversation
    Fireside Conversation 10:45 – 11:25 AM

    Courageous Conversations: Using Your Voice to Shape the Futurey:
    A reflective conversation on the inner work of leadership and how personal growth shapes leadership impact.
    with Adam Witty

Choose ONE of the following interactive sessions:

  • Leadership Lab 1
    Leadership Lab 1 11:25 AM – 12:25 PM

    Harnessing Data for Smarter People Decisions
    with Rawati Heeraman

  • Leadership Lab 2
    Leadership Lab 2 11:25 AM – 12:25 PM

    AI at Your Desk: Putting AI to Work in Your Day-to-Day
    with Kareem Williams

  • Networking Lunch 12:25 – 1:55 PM
  • Fireside Conversation
    Fireside Conversation 10:45 – 11:25 AM

    The Future of Work Cultures: Psychological Safety, Trust, and Accountability:
    An insightful discussion on how leaders can create cultures where trust, psychological safety, and accountability thrive.
    with Dr. Luz Longsworth

  • Leadership Forum 2:35 – 3:20 PM

    Well-Being as Strategy: Mental Health, Burnout, and Balance:
    A discussion on how organizations can prioritize well-being as a strategic leadership priority.
    with Nadine McNeil, Ryan Utsman, Marissa Toussaint

  • Conference Closing Address
    Conference Closing Address 3:20 – 4:05 PM

    Shaping Bold Futures Through Inclusive Leadership:
    The final address of the conference, exploring how inclusive leadership will shape the organizations and societies of tomorrow.
    with Carina Cockburn

HOTEL ACCOMMODATIONS

Enjoy a special booking rate at the Hilton Aventura, Miami
Use code “GOBLUE” for your Conference Discount

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at the Edge of Tomorrow

Join bold, forward-thinking leaders from across the Caribbean and beyond for two transformational days of learning, connection, and celebration.

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2026 Disruptive Leadership Conference

The Future Won’t Wait.

Neither Should You.

Seats are limited. Join the movement of bold, brave Caribbean leaders shaping tomorrow.

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