A case study approach was used to examine the perspectives of three high school department chairs and their work at providing instructional supervision to the teachers in their departments: math, science, and social studies. We sought to discover the beliefs and practices of three department chairs in one high school, located in a southeastern state. From interview data, three primary findings emerged: 1) The high school department chairs experienced role conflict and ambiguity relative to providing instructional supervision; 2) The meaning of instructional supervision for the department chairs was intuitive and reflected in differentiated approaches; and 3) The constraints of instructional supervision include time and lack of emphasis. The findings indicate that the department chairs were not prepared for the practice of instructional supervision in that the participants received little instruction to enact the role of instructional supervisor, and the participants were compelled to create their own roles given the lack of direction by the principal. The participants indicated instructional supervision was not a "priority" of either system or local school administrators. The participants did evidence some important knowledge concerning instructional supervision, albeit intuitively concluded rather than formally learned.