The purpose of this qualitative, phenomenological study was to understand why black Caribbean women were underrepresented in leadership positions. Semi-structured interview protocols were used to gather the data from ten female leaders who were in senior-level positions in the business sector and academia. The findings showed that black Caribbean women have progressed academically at increasing rates, however, their roles in leadership positions have not increased correspondingly. Additionally, it was revealed that organizational support for mentoring and career networking is currently needed to develop leadership skills for black Caribbean leaders and aspiring leaders to attain and maintain career progression in their desired leadership positions. Well-developed programs would help to create gender diversity and ample opportunities for black Caribbean women.