Mentorship Advocated for Young Men by Mr Executive Challenge Founder, Winston Cumberbatch

Founder and producer of the Mr Executive Interschool Business and Gentleman’s Challenge, Winston Cumberbatch, wants to see greater focus on the importance of mentorship and guidance for young men, particularly during their early years of secondary school life.

He told the EduCreations Caribbean and the Barbados Entrepreneurship Foundation graduation ceremony of the 2025 Mr Executive Business Challenge, at Solidarity House, of the critical phase in a young man’s life when he begins to assert his independence, often in third form, where influences, both positive and negative, can shape his future.

“The value is in the fact that these young men often have a decision to make at a certain point in their lives; oftentimes it is when they begin at the level of third form, when they begin to feel they are men, but are not quite there yet. They begin to challenge everything…authority at home, at school, even the law sometimes. It is at that time that there are vultures I want to call them… unfortunately we do have individuals who are on the blocks lurking and waiting for these young men as soon as they leave school, to pull them into that society.

“Once they get there, sometimes there is not any turning back,” he said.

Cumberbatch, who spoke glowingly of the young men who have entered the developmental programme over the years, said former winners of the initiative have also seen the need for early intervention, and as such, have decided to form a new association.

“You know every year we would have finalists, one of them would ultimately become Mr Executive, and after the fifth [iteration] the idea came to form an association. The association is called MEFA – Mr Executive Finalist Association, [which has] all the students that would have reached the finals.

“They would be looking to mentor and assist the finalists each year, they would be looking to go back into the schools and promote the Mr Executive Challenge, and they would be also looking to start an initiative called SAVE, Students Against Violence Everywhere,” he revealed.

The Mr Executive Senior Boys Business and Gentleman’s Challenge was established in 2017 by Cumberbatch, former head of the 5th and 6th-year levels at St. Leonard’s Boys’ School in Barbados. Following its success at the school, the programme expanded to include secondary schools across the island. Its mission is to instil strong business ethics, entrepreneurial skills, and a sense of social responsibility in students, equipping them for success in both their personal and professional lives.