What do Trinidadian executives confront as they come to lead Jamaican companies? What are the biggest obstacles they face? Where do they get in trouble? What surprises them the most? In a report from our breakthrough 2006 study, we attempt to answer these and other related questions based on interviews with over 30 executives. While we looked specifically at Trinidadian executives, the lessons learned here apply to any executive moving to lead a company in Jamaica.