The purpose of this study was to examine the phenomenon of the decision making process among secondary school leaders as they engage in an academic file review in order to make decisions regarding academic placement of a newly enrolled student. During a semi-structured interview, secondary school principals were asked to engage in a document analysis using an authentic student profile and describe how they would determine the most appropriate academic program placement for the student. Authentic insights from the perspectives of secondary school principals defined experiences and factors that influence decision making processes. Through a semi-structured, open-ended interview with secondary school principals and a document analysis of a student comprehensive file, the researcher analyzed the responses and described the experiences of secondary school principals engaged in the academic planning process for a student. Findings and recommendations for practice are included.