Technical and vocational education has become a strong focus area for Caribbean countries as they seek to advance their social and economic status in the globally competitive market. Given this context, schools in the Caribbean offer technical and vocational education and training (TVET) subjects to students from various examining bodies. This paper looks at how schools in Jamaica are doing in TVET in the Caribbean Secondary Education Certificate (CSEC) examinations and the leadership and management principles and practices used in administering TVET in selected top performing schools.