Since 2021, the Catholic Church has been engaged in a process of feedback gathering, communal reflection and discernment regarding the questions, “how are we living as Church today, and how might we become even more a Church on mission?” For a diverse global community of over 1 billion Catholics and an institution over two thousand years old, this process has introduced an unprecedented level of complexity as the Catholic Church engages two key polarities: authority and participation; and unity and diversity, among others. Since the start of this process, Fr. David McCallum, SJ, Ed.D, has been involved in the development of methodologies to support the Church in these efforts, and he serves as the executive director of a leadership formation program (www.discerningleadership.org) that supports senior officials within the Vatican and the superior generals of religious orders in grappling with the implications of this process for their roles and responsibilities. In our conversation, Fr. David will share some highlights and challenges from his experience, and we will explore the ways that complexity theory and generative learning practices shed light on this work.