There is immense pressure on school leaders to show evidence of continual school improvement. To drive these improvement efforts, there are essential considerations when planning for implementation, specifically the development of a system that supports reflective practices to increase teacher autonomy and improved student outcomes. The research presented in this article explores the attitudes and beliefs that teachers and administrators have for reflective practices through the supervisory actions of administrators in a rural Northern state. The findings from this study include, 1) the importance of a formal leadership role and the lens used when considering evaluative and non-evaluative feedback; 2) the use of reflective practices to drive changes to instructional practices; and, 3) the connection of reflective practices to school culture, professional development, and student engagement. These findings are important in that they are practical to schools and inform how the United States (US) education system might shift policies to support more formative practices that target instructional improvement.