This self-study researched my professional development as a teacher educator who was supervising and teaching Graduate Teaching Assistants (GTAs). I chose self-study as my research method primarily because it allowed me to document and study my own pedagogical thoughts and actions in relation to my supervisees, construct my personal practical knowledge out of my experiences and introspection, and have my subsequent actions progressively reflect the newly generated knowledge. The research questions are: (1) In what ways are my assumptions and actions as a supervisor challenged? and (2) How do tensions that arise during my work with GTAs in instructional practices, professionalism, and idea-elicitation contribute to the refinement of my clinical pedagogy? To answer these questions, I reflected on my dual-role experience working with GTAs based on Burns and Badiali's conceptual framework for clinical pedagogical skills, foregrounded the process and the tensions as I tried to grow as a supervisor, and listened to my own varied voices as interpretative lenses to study my action. I want to share my findings with others who are in similar situations as teacher educators seeking to prepare novice instructors and simultaneously manage frustrations. I also aspire to reach novice teachers who are interested in understanding the clinical faculty's side of the process. The challenges, tensions, and development in clinical pedagogy examined in this article offer insights on teacher preparation and contribute to the creation of a more productive and collegial experience of teacher education for both supervisors and supervisees.