My dissertation investigates how principals in rural Massachusetts districts seek to improve instructional practices, focusing on the implementation of teacher evaluation. It examines how their beliefs and attitudes shape their planning and actions within an environment influenced by various stakeholder expectations and demands. Additionally, this study highlights how principals navigate the challenges of using teacher evaluation as a tool for school improvement, considering characteristics commonly found in rural school settings, though not necessarily unique. Essentially, I aim to understand how principals' beliefs and attitudes drive their actions and to identify patterns in strategic planning related to the teacher evaluation process in rural schools, which can inform the development of tailored professional support for rural principals. My findings indicate that, overall, principals in rural areas tend to plan and act in ways that extract value from the teacher evaluation process, aiming to improve instruction. Their strategic decisions aligned with their beliefs and tended to emphasize the context of their schools. Specifically, I discovered that principals in rural schools focus on building trust and creating opportunities for teachers to collaborate regarding teacher evaluation. My evidence also indicated that, due to the remoteness often characteristic of rural schools, they tended to view teacher expertise as a key component of this process. They reported actively seeking involvement from teachers to help carry out their responsibilities related to teacher evaluation. My evidence also indicates that as principals develop strategies for teacher evaluation, they manage a complex array of expectations driven by local policies and state laws aimed at promoting high-quality instruction. Essentially, they continuously balance teachers' individual instructional needs with these expectations by creating allowable variances (an affordance of the system) and employing context-setting strategies to adapt their practices.