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This chapter explores barriers new middle leaders encounter as they enact their roles and employ strategies to overcome these challenges. It can be argued that principals need to collaborate with other leaders on various levels of the school. This collaboration can harness the expertise of teachers in the organization and play an equally significant role in the construction of leadership practices in the school—a process called distributed leadership. However, for distributed leadership to work well, principals need to remove barriers that prevent middle leaders (heads of departments and deans) from interacting and collaborating with teachers. A qualitative multi-site case study was employed to generate pertinent data from six secondary schools in a single education district. The sample comprised six principals, 25 middle leaders, and 67 teachers. Data were collected using semi-structured interviews to garner the perspectives of principals, middle leaders, and teachers. Respondent triangulation was used to mitigate the absence of observation. The findings suggest that the following factors stymied middle leaders’ ability to enact their roles: principals’ leadership style, role ambiguity, role conflict, role overload, time constraints, and inadequate training. The findings also suggest that middle leaders used the following strategies to overcome barriers: middle leaders’ job description, deferral of issues to senior management, avoidance of conflict, big stick approach, and use of reminders.

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