Leadership Cayman 2026 Cohort Begins Their Journey at Orientation Dinner

The Cayman Islands Chamber of Commerce officially launched the Leadership Cayman Class of 2026 began their journey of discovery at the Orientation Dinner, held last night (14 January) at Grand Old House. The evening marked the first time the newly selected 25 professionals came together to begin one of the Cayman Islands’ most respected leadership development experiences. Established by the Chamber in 2009, Leadership Cayman is a six-month immersive programme designed to deepen participants’ understanding of the social, economic, and political landscape of the Cayman Islands. It remains the only programme of its kind locally, offering bi-weekly seminars, site visits, and direct engagement with senior leaders across key sectors. 

Warm Welcome 

From Chamber Leadership Cristina Spratt, Chamber President-Elect, Leadership Cayman alumna, and former Planning Committee Chair, opened the event with a message about connection and growth. She emphasised that the cohort’s diversity—from finance and law to government, entrepreneurship, and the nonprofit sector—would be one of their greatest strengths over the months ahead. Echoing sentiments widely shared through the programme’s alumni network, she noted that Leadership Cayman often creates a sense of family, bringing together professionals who may never otherwise cross paths. Her remarks set the tone for an evening that was both inspiring and energising, encouraging participants to embrace the programme fully and step outside their usual professional silos.
Encouragement 

From the Planning Committee 

Melissa Whorms, Chairperson of the 2026 Planning Committee and Class of 2021 graduate, offered a warm and honest perspective on what awaits the cohort. She encouraged participants to prepare for deep discussions, moments of challenge, and unexpected personal growth. Drawing from her own experience, she shared that the seminars often sparked such engaging dialogue that she found herself simply absorbing the perspectives of others—a reminder of the richness that comes from learning directly from Cayman’s leaders and institutions. 

Ice-Breakers That Revealed the Cohort’s Creativity 

A lively ice-breaker quickly helped the group warm up: each participant introduced themselves, shared what they do, and then named a Marvel-style “superpower” they wished they had. The twist—no superpower could be repeated—forced participants to get inventive as the evening went on. What began as classic choices soon evolved into imaginative and humorous abilities, revealing personality and creativity while showcasing the value of bringing such a wide range of professions and backgrounds together. This diversity—accountants, lawyers, government officers, entrepreneurs, financial experts, creatives, and more—is one of the programme’s greatest strengths. 

Alumni Reflections: Growth 

Through Connection Several alumni shared reflections throughout the evening, emphasising that Leadership Cayman’s impact often lies in the unexpected: meeting people outside one’s industry, hearing perspectives not encountered in day-to-day work, and discovering new ways of thinking about community leadership. They described the programme as one that both challenges and expands participants’ understanding of the Cayman Islands and their role within it—insights echoed in Chamber reporting on past cohorts. Their contributions reinforced the sense that the 2026 cohort was stepping into a well-supported, dynamic learning community. A Strong Start to the Six-Month Journey 

As dinner concluded, participants mingled in small groups, connecting with each other and with attending alumni. The discussions were warm, lively, and filled with anticipation—an early sign of the bonds that often form during the programme. Chamber Programmes Coordinator Jada Ramoon said: “I was very happy with the turn out for the Orientation Dinner. This year’s group seems very enthusiastic to begin the 6 month process, and they have started to get along so well already I have high hopes for this year’s Leadership Cayman class, and I cannot wait to see what this group will accomplish throughout the programme. The evening captured the spirit of Leadership Cayman: openness, curiosity, and shared purpose. 

Next on the Agenda: 

The Sister Islands Opening Retreat The cohort will next travel to Cayman Brac from 22–24 January for the programme’s signature Opening Retreat, which features team-building exercises, leadership development workshops based on the Leadership Tampa model, and in-depth discussions in the unique setting of the Sister Islands. This retreat is followed by the Sister Islands Seminar, kicking off the bi-weekly series of sessions that explore core national issues—including government, sustainability, tourism, education, infrastructure, and more.