On 12 July Leadership Cayman Class of 2025 will graduate after spending six months developing their leadership skills.
The Chamber of Commerce programme, now in its 15th year, offers 24 individuals the chance to take part in leadership workshops, a class project for charity, and 12 bi-weekly interactive seminars, featuring site visits across industries and panel discussions with expert local leaders.
As the 2025 group approach the end of their course, applications have just opened for 2026.
To explain what the programme is all about and who it’s for, Cayman Independent spoke to the chair of this year’s class, James Robinson.
Robinson, a consulting senior manager at Big Four accounting/consultancy firm EY, was co-chair last year and went through the course himself in 2021.
Who is Leadership Cayman for and how do you become part of the programme?
Leadership Cayman is open to anyone aged 25 and above who is currently a leader at their place of work, from middle management and above.
Participants can be from any sector where there are leadership possibilities.
In this year’s cohort there is a university dean, several marketing individuals, a couple of police investigators, accountants, lawyers, non-profit workers and people in government roles.
Applicants fill in an application form and if selected, they’ll go through to the interview stage. It’s two interviews in total and they’re not long, around five to 10 minutes.
Then in late November/early December time a team of 24 people is selected, before the programme starts in January.
What are the aims of the programme?
The motto of the programme is ‘Learn, grow and connect’.
After the six months it’s hoped you’ve gained a deeper understanding of the many aspects that make up the Cayman Islands, from its judicial system and government to its culture, heritage and environment.
Your leadership skills should also have grown, and you’ll hopefully have made valuable connections with people in various industries, and with your fellow programme participants.
What happens during the six months?
The programme starts with an opening retreat on Cayman Brac, where the group stays for three days, usually from Thursday to Saturday.
The first two days will be leadership workshops led by an individual from the Leadership Tampa programme that really help you understand who you are as a leader and the different type of leaders there are.
Then on the Saturday the group will explore Cayman Brac, basically getting on a bus and touring around, before heading back to Grand Cayman in the evening. Sometimes they’ll do Little Cayman as well.
After that there are 12 different seminars that happen over the six months, which each cover one of the various aspects of the islands I mentioned earlier.
Each seminar is planned by two members of the class and will involve a tour and a panel discussion with industry leaders.
So, for example, for the criminal justice seminar this year the class visited the prison.
There has been talk of renovating the facility, so the group wanted to find out more about the current conditions – which they’d heard from news reports was bad – and what impact this was having on inmates.
As part of the seminar we toured the prison then listened to a panel discussion from Cayman’s police commissioner, the director of public prosecutors and a magistrate.
Afterwards the class will reconvene to reflect on what they seen and learnt.
As well as the seminars, the class will choose a project to work together on in aid of a chosen charity.
This year the team organised the islands’ first Heritage Hunt, which was a scavenger hunt around Grand Cayman raising money for the National Trust and awareness of its heritage sites.
Everyone had different roles to play in the planning and running of the project, sometimes this was in areas they were familiar with and other times they’d take something on that was more of a challenge.
The final part of the programme is the graduation ceremony and celebration in July, which is organised by three or four of the class who have been chosen by a vote. This year they’re doing a weekend of activities to mark the occasion.
Why did you apply to take part in the course and what did you gain from it?
I’m from the US and when I moved here I wanted to immerse myself in the culture as much as I could as well as give something back and connect with people I may not otherwise have access to.
I also wanted to become a better leader, so applying for a place on the Leadership Cayman programme made a lot of sense.
In terms of what I gained, I learnt a lot about the various aspects of the Cayman Islands, which has been really useful, and I feel I got the chance to give back and hopefully can continue to do so with the connections I’ve made and knowledge I’ve built.
I also believe I became a better leader. I’m a talkative person and I learned to become more of an active listener, which has really helped me in my career.
Another big gain were the good friends I made – a couple of them are now my running buddies!
There’s a CI$75 non-refundable fee to apply for a place on Leadership Cayman. If you secure a spot, it costs $2,600 for chamber members and $2,850 for non-members.
To learn more about the programme and apply to be part of next year’s cohort, visit the Leadership Cayman website.
