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Through semi-structured interviews, this study focused on understanding the transition of former school counselors into school administration. Research shows that school counselors often struggle in their roles because their school administrators do not understand their role and how to leverage them to address school priorities. After interviewing six school administrators, preliminary findings indicate that former school counselors who transitioned into school administration are well-positioned to become school administrators given their holistic understanding of school systems, collaboration with all school community members, and training as school counselors to be active listeners, problem-solvers, and multi-taskers. Results from the study inform leadership pipelines in school districts, school administrator training, and school counselor training.