This study district provides ongoing professional development for teachers; however, there was little evidence that transfer of training was occurring and it was unclear whether the administrator role could improve the implementation of learning from professional development. The purpose of the study was to examine teachers' perceptions of administrative involvement in professional development in order to identify indicators that could strengthen nonevaluative, collaborative relationships leading to higher rates of transfer. The central research question focused on teachers' perceptions of the roles of administrator-as-evaluator and administrator-as-collaborator and whether collaboration might influence transfer of training for teachers as they strive to improve their instructional practice. The conceptual frameworks that grounded this study were professional development and transfer of training. Participants in the study were a group of randomly selected secondary level teacher leaders in a school district (n = 10). An open-ended narrative questionnaire and focus group interview were used to collect data that were then open coded and thematically analyzed. A key finding was that these 10 teachers wanted administrative involvement in professional development; however, they wanted administrative oversight, coordination, and structure rather than side-by-side instructional collaborators. A white paper was created to assist local district administrators with addressing the transfer of training needs of teachers by outlining specific protocols and structures that will lead to systemic, on-going professional growth. A school culture that is characterized by structured collaboration will lead to positive social change in that instruction will meet the needs of all students and prepare them for life after high school.