School leaders are expected to play an important role in the implementation and development of monitoring systems that enhance and sustain good educational performance. Implementing these governance tenets is not an easy task and requires dedication, which can sometimes be complicated by the different contexts where schools are situated. This chapter explores the roles of principals in managing teaching and learning in multiple deprived contexts which are affected by limitations of social inequalities in public secondary schools. This study that underpins this chapter followed a narrative inquiry methodology and a qualitative approach. It is the narrated story of successful secondary school principals who are performing well even though their schools are situated in socially affected areas and lack resources. The principals of the schools under discussion took the initiative to ensure that teaching and learning take place to achieve good academic results. This chapter discusses how the principals’ roles have a bearing on learner’s performance; however, other stakeholders must also be involved in teaching and learning to ensure good learner’s performance. The main study findings reveal that the principals were aware of the school context and used collaborative leadership to involve all stakeholders in ensuring that teaching and learning took place. Delegating duties to all stakeholders promoted teamwork and accountability in their schools, with monitoring being used as a key tool for managing teaching and learning. Principals were also involved in teaching and learning, and discipline was applied to teachers and learners who did not attend classes.