Since both modern and traditional ways of life are observed in Lesotho, community members often find themselves in a complex situation, being either citizens in relation to local councillors or subjects of traditional leaders. Local councillors preside over contemporary democratic laws, policies and processes in a manner that stifles the genuine role and influence of traditional leaders. Notwithstanding these far-reaching implications in post-colonial settings, traditional leaders continue to receive popular support in Lesotho. This chapter employs a qualitative research method grounded in a critical desktop literature review. It examines the legal, institutional, and structural challenges that impede the efficiency and effectiveness of traditional leadership in the local government system and seeks solutions to enhance its role in Lesotho’s local government system.