In this conversation with Paul Anwandter of INPACT, Santiago de Chile, in October 2018, we discuss the new landscape of mentoring that includes applying insights from research in adult development. We discuss the obstacles and failures but also the challenges of such mentoring in reference to a class on developmental coaching I teach at INPACT, a yearly event that concludes the INPACT coaching program. An important issue in the discussion is the difference between U.S. and South American organizational culture.