The purpose of this research was to explore how principals in eight high-functioning elementary schools in one American school district balanced teacher supervision and evaluation in their role as an instructional leader. Using the theoretical framework of "wicked problems," to unpack the circular used to problematize teacher supervision and evaluation, the findings analyse how elementary principals in these eight buildings acknowledge the tensions and conflicts between supervision and evaluation, specifically as they relate to improving teacher instruction. Specifically, the results of this study highlight not only the differences between supervision and evaluation, but also the intersection between the two functions, as well as how high-performing elementary school principals serve as an instructional coach rather than a manager of teachers. While the two functions of supervision and evaluation are inherently different, it is the acknowledgement of the intersection between the two functions that can allow building principals to progress as instructional coaches who can better develop human resources and create higher-functioning school systems. Overall, this study points toward the importance of elementary principals having the instructional leadership skills to differentiate supervision and professional development need for teachers, which in turn influences the evaluation of a teacher is in her/his respective career.