Limited existing research indicates that high school department chairs may not be prepared to fulfill their duties because of varying role descriptions and training. This qualitative comparative layered case study examined the alignment of high school department chairs' contextual intelligence in an eastern seaboard region of the United States from 3 perspectives: (a) school districts' role descriptions, (b) local universities' leadership courses, and (c) a state's education department's licensure requirements. Sternberg's contextual intelligence, the learned skill of decision-making based on past experiences, present settings, and future ideals, conceptually framed this study. The primary research question explored the extent to which conceptual similarities existed amongst those perspectives. Purposeful, chain, and stratified sampling techniques were used. Institutions' public email addresses were used to request participation from 10 education professors, 21 high school department chairs, and 41 school departments. Three education professors and 4 department chairs participated in semistructured interviews. The education department's website and 6 school districts provided artifact data. Inductive and deductive content analysis strategies were used to identify, compare, and triangulate themes. Findings suggest that state department's licensure requirements for supervisor/director align with local universities' leadership courses but may not align with local school districts' department chair role descriptions. Thus, participating school districts may need to revisit role descriptions. These findings may promote positive social change by influencing school districts, universities, and a state's education department to continue to recognize and develop high school department chairs' contextual intelligence.