Thesis advisor: Patrick Proctor / This study aimed to explore middle leadership from a single K-12 district. To accomplish this, an exploratory, embedded single case study (Yin, 2018) was utilized. The district was the case while one elementary, middle, and high school were embedded “sub-units” in the case. A principal, middle leader, and 2 middle leader colleagues further represented each school. This method was employed in order to illuminate how middle leadership was experienced through multiple perspectives and contexts but within the same district. This dissertation also took a narrative approach, beginning in understanding the conditions that led to the creation of middle leadership roles, to the selection, conceptualization, and evaluations of middle leaders. Then, middle leaders were asked about how the district can further support their roles. Results indicated that external (standardized tests, changes in standards or curriculum) and internal (desire for district consistency and cohesion) and factors influenced the creation of middle leadership positions. Middle leaders were selected based on their teaching and leadership experiences. However, conceptualization of middle leaders in the district extended beyond teaching. In addition to teaching, middle leaders were also conceptualized as strategic planners, people with good interpersonal and communication skills, managers, coaches, and evaluators. Evaluation of middle leaders were based on state-based evaluation frameworks for teachers or administrators that showcased a misalignment of responsibility and evaluation processes. To support their roles in the district, middle leaders suggested a combination of internal and external support. Internally, they suggested the creation of a within-district, middle leader-specific professional learning community in order to have opportunities to share best practices and collectively think about problems and solutions. Externally, they would also appreciate the district’s support in attending formal professional development such as courses or certification programs. These results indicate that there is a need for middle leadership-specific classes, programs, and evaluation frameworks and that middle leaders would also benefit greatly in the creation of mentorship programs or professional learning communities. / Thesis (PhD) — Boston College, 2020. / Submitted to: Boston College. Lynch School of Education. / Discipline: Teacher Education, Special Education, Curriculum and Instruction.