This chapter examines some of the most widely accepted leadership styles deployed in Zambian colleges and their impact on employee well-being outcomes such as employee stress, well-being, productivity, turnover, and absenteeism. The leadership styles assessed include transactional, laissez-faire, autocratic, authoritarian, and transformational leadership. Qualitative comparative design is used to capture and understand the interplay between leadership styles and organisational well-being. The chapter will explain at length the advantages of more relational leadership styles (i.e., transformational leadership) in terms of reduced stress, turnover, and absenteeism in Zambian colleges of education.