This study examines how mentoring through post observation conversations can provide opportunities for feedback and teacher reflection as part of teacher professional development. Using Conversation Analysis, and building on our previous work, we draw attention to procedural details by which a different role within the professional role-set is enacted in post observation conversation: feedback-provider vs. facilitator of reflection. The different role enactment constructs some episodes as more feedback-oriented while others are more reflection-oriented. Furthermore, the analysis illustrates how “reflecting through conversations is a discursive process”, situated within the matrix of interaction, which in turn, is shaped and constrained by sequential organization. This study shows the applicability of Conversation Analysis as an approach to better understanding post observation conversations and presents a few suggestions for better handling such interaction for teacher professional development.