A review of a study of leadership styles and job satisfication at a Caribbean high school is reported. Using an adapted LBDQ survey and a researcher-constructed job satisfaction questionnaire, a positive correlation was found between leadership style and the degree of job satisfaction (R = .70; p<.01). A stronger correlation existed between the consideration "leadership style" and teacher job satisfaction (R = .70) than between initiating structure and teacher job satisfaction (R = .50). The review explores methodological changes that might give better insights into leadership style and job satisfaction, especially because of the increasing complexity demanded of leaders in the emergent digital age. The method was found appropriate to obtain preliminary data but not the additional data required for triangulation and in-depth analyses that have a futuristic value. A conceptual matrix was recommended to improve data collection, analyses of data, and reporting.