This study explored the extent of agreement between principals and teachers relative to the teachers' style, the extent of agreement between principals and teachers relative to the most effective match between teachers and students with various characteristics, and how classroom placement decisions are made. Participants consisted of 25 principals and 61 teachers. Principals and teachers completed the Teaching Style Inventory (Grasha, 1996) as a description of the teacher's teaching style. Then, participants reviewed three vignettes of students with varying characteristics and completed a Teaching Style Inventory, to identify the style they thought appropriate for each student. An additional 5 principals and 5 teachers were interviewed to explore the class placement process used in the participants' schools. Results revealed that principals and teachers were not in agreement in their ratings of teacher style, with principals rating teachers significantly higher on the delegator style, than teachers rated themselves. Principals and teachers also did not agree with each other in their ratings of the teacher styles needed by the students. Significant differences were found in the ratings depending on who completed the measures (principal or teacher). In interviews, class placement decisions were reported to be based on students' academic and social-emotional/behavioral skills, need for supplemental support services, and parent feedback, but not teaching style, as anticipated. Teaching style, however, was considered as a part of the conceptualization of the term "match". Implications are discussed relative to the class placement process and educator evaluation systems.