The purpose of this theoretical study is expressed through the following research question: What potential does third-generation coaching as transformative dialogue hold for school leadership for equity and social justice? The research question is explored through two sub-questions: (1) What characterizes first-, second-, and third-generation coaching? (2) What is unique about third-generation coaching? The chapter is organized as follows: Initially, it explores and defines coaching in relation to and, although overlapping, distinct from therapy, advice, consulting, supervision, mentoring, facilitation, and even teaching. Then it describes what characteristics there are between first-, second-, and third-generation coaching. Following that, it describes what is unique with third-generation coaching in the light of three main characteristics of our society: globalization, complexity, and reflexivity. The discussion revolves around three essential aspects for understanding third-generation coaching: value orienting, sensemaking, and narrative co-creation. It is argued that these aspects show the potential for extending the coaching’s reflexive room and how to ensure a deep dialogue about establishing equity and social justice. The chapter contributes to the literature by emphasizing how school leaders through dialogue can use the potential for self-reflection, to explore and understand challenges fundamentally on a personal level. Likewise, transformative dialogue aims to create space for reflection for meaning and understanding related to specific situations. Moreover, transformative dialogue invites school leaders and teachers, and even students to change their perspectives. In sum it extends simple solutions and urge them to deeply investigate their challenges, which is a critical potential in an increasingly complex society.