Given the critical importance of Technical and Vocational Education and Training (TVET) and the effectiveness of transformational leadership in improving individual and organizational performance, this study was conducted to explore the challenges Jamaican TVET leaders faced in practicing transformational leadership and to identify strategies that could be employed to improve transformational leadership practices among Jamaican TVET leaders. The study was guided by Kouzes and Posner's (2002a) Five Practices of Exemplary Leadership and the following three research questions: 1. How are Jamaican TVET leaders perceived in relation to Kouzes and Posner's Five Practices of Exemplary Leadership? What are the challenges faced by Jamaican TVET leaders in practicing transformational leadership? What do Jamaican TVET leaders perceive as potential strategies that could enhance their practice of transformational leadership within TVET in Jamaica? The study employed a generic qualitative research approach and used purposive sampling to select 12 TVET leaders as the participants for the study. Semi-structured interviews were used as the data collection strategy and thematic analysis as the data analysis method. The study found that Jamaican TVET leaders were perceived poorly regarding transformational leadership. The challenges faced in practicing transformational leadership were that the organizational culture stifles transformational leadership, they lack adequate leadership preparation and adequate understanding of TVET, and the system overly focuses on management and quantitative outcomes. The study found that the strategies that could enhance the practice of transformational leadership in TVET in Jamaica were leadership preparation, capacity building, TVET leadership programme, TVET leadership framework, transformational leadership culture, and industry awareness, collaboration, and international exposure. The study recommends the development of a new national TVET policy, a national TVET strategic plan, a national TVET leadership development plan, a national TVET leadership training programme, the repositioning of the Vocational Training Development Institute (VTDI) to offer TVET leadership programme, the organizational transformation of HEART/NSTA, revision of the performance management and appraisal system for TVET leaders, adoption of International Standards Organization (ISO) quality management framework, and bilateral and multilateral collaboration. A major contribution of the study is the conceptualization of the Transformational TVET Leadership Development Model as a framework to guide the assessment, preparation, and ongoing development of TVET leaders. The study has the potential to make a significant contribution to improving TVET leadership and advancing the cause of TVET as a key strategy for national development. [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://bibliotheek.ehb.be:2222/en-US/products/dissertations/individuals.shtml.]