Leadership Cayman 2026 Explores the Sister Islands Experience
The Leadership Cayman Class of 2026 has officially begun its six?month journey of deep learning, connection, and community engagement. Fresh from their Orientation Dinner at Grand Old House on 14 January — the first time the newly selected 25 professionals gathered as a cohort — participants stepped immediately into one of the programme’s most defining experiences: the annual Sister Islands Opening Retreat on Cayman Brac.
For years, this retreat has served as the opening immersion into Leadership Cayman’s signature method of experiential learning, encouraging participants to step outside their daily environments and examine leadership through new lenses. The 2026 class followed this well?established pattern, travelling to Cayman Brac for several days of workshops, reflection, and hands?on exploration designed to build trust and set the tone for the months ahead.
Central to the retreat is the intensive leadership workshop that spans the first two days. As in previous years, the sessions were facilitated by Dr. Peter Hammerschmidt, a specialist in team building and conflict resolution, who guided participants through a series of interactive exercises, personality insights, and collaborative challenges that helped them better understand their leadership styles.
Programme Coordinator Jada Ramoon reflected on the energy and cohesion of the new cohort, sharing:
“The opening retreat was a massive success; the class was very interactive with Dr. Hammerschmidt. They all meshed so well together and hit it off immediately. I am looking forward to continuing to work with the class and to see what they will achieve.”
A central highlight of the retreat each year is the Sister Islands Perspective seminar, held on the Friday evening. This year’s seminar featured a three?speaker panel, each offering a unique lens on life, leadership, and community development in Cayman Brac and Little Cayman.
Mark Tibbetts, Cert. Hon., JP, District Commissioner of Cayman Brac & Little Cayman, provided an authoritative overview of the Sister Islands’ priorities, infrastructure, and governance.
Inspector Leslie Laing?Hall, Area Commander for Cayman Brac, offered insights into community policing, public safety, and the evolving needs of the Sister Islands population.
Mr. Josh Baker, Deputy Registrar & Campus Manager of the UCCI Cayman Brac Campus, spoke about tertiary education, workforce preparedness, and opportunities for upskilling within the local community.
Together, the panel gave participants a multifaceted and grounded understanding of the opportunities and challenges unique to the Sister Islands, reinforcing how local leadership intersects with community heritage, public services, and long?term development.
No Sister Islands retreat is complete without exploring Cayman Brac itself. True to tradition, the class set out on a guided tour, including stops at the iconic Lighthouse perched high on the bluff, a visit to the historic Heritage House, and lunch at the farm?to?table restaurant Le Soleil. In past years, the itinerary has also included a walkthrough of Faith Hospital, giving participants insight into the healthcare landscape of the Sister Islands.
As the cohort returns to Grand Cayman to begin their full schedule of bi?weekly seminars, site visits, and leadership dialogues, the foundation laid in Cayman Brac becomes an anchor for the months ahead. Alumni frequently describe the retreat as the moment the class begins to feel like a family — a sentiment clearly shared by this year’s participants, who stepped into the experience with enthusiasm, curiosity, and a shared commitment to growth.
With the Sister Islands retreat complete, the Leadership Cayman Class of 2026 is now fully underway, poised to explore the major social, economic, and civic issues shaping the future of the Cayman Islands.