This qualitative study was premised on the affirmed belief of the researcher that many individuals who aspire to serve in leadership roles across various educational organizations are often unaware as to the core/foundational responsibilities and associated actions for creating and sustaining an environment that is conducive to effective strategic conceptualizing and operational best-practices. An absence of such prerequisite mindfulness when it comes to leadership, results in there being an existential threat to kind of leadership that is needed to drive efficiency while impacting the well-being of their followers. For this study, "Examining leadership styles in Higher Education Institutions (HEIs) in Kingston, Jamaica: A comparative study of a public and private institution", is relevant to bring awareness to leaders at each level within organizations. The leadership styles examined by the study include transformational, transactional, charismatic, situational, and competency leadership styles as these leadership styles have been commonly portrayed in Jamaica over the past five years. Some leaders may be unaware of their leadership style, and this paper can be used as a guide to improve leaders' ability to impact all stakeholders. Examining leadership styles in HEIs in Kingston, Jamaica is important because it should yield an improved organizational culture, a proactive impact on crisis management, a fostering of strategic partnerships, improved programs, and high impact on brand value with an effective workforce. There is a public demand for access to higher education that has become a potent force along with effective and efficient leadership, Altbach et al. (2010). [The dissertation citations contained here are published with the permission of ProQuest LLC. Further reproduction is prohibited without permission. Copies of dissertations may be obtained by Telephone (800) 1-800-521-0600. Web page: http://www.proquest.com/en-US/products/dissertations/individuals.shtml.]