Educational leadership and management are central to achieving equitable learning outcomes and efficient resource utilisation within Kenya's evolving education system. The transition to the Competency-Based Curriculum (CBC) and the decentralisation framework established under the 2010 Constitution have fundamentally restructured the roles of school leaders across Kenya's 47 counties. Drawing on a qualitative comparative case study methodology and secondary data from Ministry of Education reports, Kenya National Bureau of Statistics surveys, and peer-reviewed literature, this paper examines county-level leadership practices in Uasin Gishu, Kericho, and Nairobi counties, as well as Technical and Vocational Education and Training (TVET) institutions. The findings reveal that context-specific strategies, including community-school partnerships, mentorship programs, and technology-driven solutions, significantly enhance student outcomes and CBC implementation. However, persistent challenges, including resource disparities, political interference, gender inequities, limited ICT access, and inadequate TVET funding, undermine leadership effectiveness across counties. The study recommends tailored KEMI training, enhanced budgetary autonomy, strengthened school governance structures, digital infrastructure investment, gender-sensitive leadership policies, and robust monitoring and evaluation frameworks. These interventions are essential to building adaptive, inclusive, and accountable educational leadership aligned with Kenya's Vision 2030 and Sustainable Development Goal 4.