Executive leadership and development in relation to expatriation have been vastly researched over the years within various industries particularly in Western and Eastern nations. Many scholars have identified the advantages expatriates possess that allows them to be perceived as more suitable for executive positions in multinational companies and by extension the hospitality industry. The Caribbean hotel sector is no exception in regards to having a high representation of expatriates occupying executive roles. The globalization of the Caribbean hotel sector, have provided employment for much of the local populace in various capacities which have also prompted an increase in local employee’s development and advancements initiatives for career progression in the sector. The Caribbean hotel sector, has been heavily criticized for favoring international foreign workers over locals for these roles and as a result, have promoted this research. The study discusses why expatriates are perceived to me more suited than local managers for executive positions by showing the advantages expatriates have over locals in the parameters of critical competency gaps and the cultural influences that exist in the Caribbean region. A qualitative approach was used for this study and data was collected from interviewing 20 participants using three sample groups of executives from different hotels operating in the Caribbean region–international executives, local executives, and human resource practioners. The study also used document reviews as secondary data. The Data analysis was done using open coding and axial coding techniques to formulate aggregate categories for the findings. The study findings identified hotel involvement and government intervention as means of aiding in the development of their local employees in terms of implementing succession planning programs, collaboration with local schools and hospitality associations and proper management of expatriate hiring. Lastly, the study provided practical implications for the hospitality industry, Human Resource practitioners and other developing countries.

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