In this LinkedIn Live session, Haesun Moon and Carol Kauffman engage in a scholarly yet practical inquiry into the intricacies of coaching efficacy. This discussion critically examines how we can ascertain the effectiveness of our coaching methodologies and understand their operative mechanisms. Dr. Moon introduces the Dialogic Orientation Quadrant (DOQ) as an innovative heuristic and pedagogical tool, iteratively designed to enable coaches to observe and refine their practice critically. We explore how cultivating curiosity not only directs the purpose of learning but also expands the spectrum of possibilities of coaching responses while benchmarking the learning progress of a coach.