Meet Judy Mccutcheon

We recently connected with Judy Mccutcheon and have shared our conversation below.

Judy, we’re thrilled to have you sharing your thoughts and lessons with our community. So, for folks who are at a stage in their life or career where they are trying to be more resilient, can you share where you get your resilience from?

My resilience stems from growing up in a small village in Tobago, raised by a single mother in a family of ten. From an early age, I had to rely on myself to navigate difficult circumstances. There were times when food was scarce, yet I still had to attend school and perform at my best. My mother instilled in us the belief that “Education is your way out of poverty,” and that mindset drove me to persevere.

I found creative ways to meet my basic needs—whether by picking fruit from the neighbour’s fruit trees or receiving a meal from a generous neighbour. These small acts of resourcefulness taught me how to adapt and push forward.

Additionally, reading became my refuge and motivator. I immersed myself in romance novels and other books that allowed me to imagine a life beyond my immediate reality. Those stories gave me hope and strengthened my belief that I could create a better future for myself.

My determination to break free from poverty and my unwavering belief in a better life fueled my resilience. Every challenge I faced became a reminder that perseverance and self-reliance would lead me to the life I envisioned.

Thanks, so before we move on maybe you can share a bit more about yourself?

I am, at my core, a passionate advocate for people and their potential. My work with companies focuses on improving profitability by empowering their greatest asset—their people. I do this by assisting organizations in crafting effective HR policies, conducting job evaluations, performing HR audits, and developing strategic plans tailored to their goals.

As a leadership development expert, I guide leaders and organizations in achieving sustainable and ethical growth. I am also a certified Leadership and Trauma-Informed Coach, specializing in helping female leaders transform their approach to leadership. By inspiring, equipping, and enhancing their capabilities, I aim to support women in stepping into leadership roles with confidence and self-awareness.

One pressing issue I’ve observed in the Caribbean is the lack of leadership mentorship programs and a consistent networking hub for women in leadership. In today’s rapidly changing environment, we need more women to step into senior leadership positions and lead with self-awareness, authenticity, and a commitment to creating opportunities for others. My executive coaching program is designed to contribute to this vision by fostering impactful leadership as part of a larger movement.

From a broader leadership perspective, I founded the Disruptive Leadership Conference, now in its 6th year. This flagship event will take place March 12-14, 2025, at the Miami Airport Sheraton and Executive Meeting Center. The conference is for leaders who are ready to lead boldly, inspire their teams, and succeed in today’s fast-evolving business landscape.

Through dynamic keynotes, expert-led workshops, and interactive panel discussions, attendees will gain the tools to:

Build resilient organizations that adapt to change with confidence.
Foster collaboration, inclusion, and motivation in the workplace.
Leverage technology and AI to drive growth and efficiency.
Attract and retain top talent while aligning organizational and personal values.

This is my mission: to help leaders and organizations thrive by focusing on what truly matters—people.

If you had to pick three qualities that are most important to develop, which three would you say matter most?

When I think of resilience, I think of my mother. Despite facing countless challenges, she never gave up. She kept moving forward, knowing that her perseverance could create the possibility of a better life for her children. For me, that’s the essence of resilience: pushing through adversity with hope and determination.

Learning to speak up and advocate for myself and others has profoundly shaped my journey. It taught me the importance of asking for what I want, knowing that if I never ask, the answer will always be no.

My deep desire to understand people led me to study psychology. This pursuit has allowed me to connect with others on a deeper, more meaningful level, fostering empathy and stronger relationships.

One piece of advice I would offer to others is to cultivate a strong sense of self—become truly self-aware. Self-awareness is the foundation of effective leadership. When you master the art of leading yourself, you unlock the ability to lead and inspire others to reach their full potential.

Thanks so much for sharing all these insights with us today. Before we go, is there a book that’s played in important role in your development?

Reading The Power of Now by Eckhart Tolle has profoundly impacted my perspective on trauma and its influence on leadership. Tolle’s emphasis on the power of presence and the importance of living in the moment has reshaped how I approach both personal and professional challenges.

One of the most impactful lessons from the book is the understanding that unresolved trauma often keeps us tethered to the past or fixated on the future, preventing us from being fully present. This lack of presence can deeply affect how we lead ourselves and others. By addressing and healing trauma, we free ourselves to lead from a place of clarity, compassion, and self-awareness.

Another key takeaway is Tolle’s insight that our pain doesn’t define us—it is an experience, not an identity. This realization has helped me to reframe difficult situations and support others in doing the same, enabling growth and resilience in the face of challenges.

The book also highlights the profound connection between self-awareness and leadership. As leaders, our ability to remain present and centered directly influences how we inspire and guide others. This has taught me that leadership is as much about inner mastery as it is about external strategy.

The Power of Now continues to be a guiding light in my journey, reminding me to approach every moment, every person, and every challenge with mindfulness and a deeper understanding of the transformative power of presence.

Contact Info:

Image Credits

DCJ Photography
Heston Williams

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