Studies have indicated that in education, the traditional management paradigm maintains an inward focus with the aim of cutting costs, upholding rules and division of labour. However, the 21st century has ushered in a new revolution in education leadership structures which are less hierarchical, more flattened and more fluid organizations. The purpose of the study was to examine the pressing issue of 21st century leadership skills gap in the secondary school sub-sector in Kenya and explore the way(s) to address it. A case study design was used which enabled the collection of qualitative data from three participants who were purposively sampled. It was guided by two research questions: which leadership skills are practiced in secondary schools in Kenya? What are the leadership skills needed for a secondary school principal in Kenya? The findings established that the secondary school principals in Kenya mainly practice the traditional management approach. They have not incorporated the 21st century leadership skills in the management of schools. These encompass traditional literacies, competencies and character qualities. It is therefore recommended that the secondary school principals in Kenya should embrace lifelong learning and systematic learning opportunities should be created to assist them develop these complex skills.