This study examined the listening behaviors of organization development (OD) practitioners that result in client transformation. Interviews conducted with eleven OD consultants with extensive experience in executive coaching pointed to engaged, focused attention as a core characteristic of their listening. OD practitioners regularly use three primary listening approaches (active, empathetic, and expansive listening) to drive insight and help clients transform their perspectives. Practitioners subsequently use two secondary listening approaches (critical and reductive listening) to anchor insight into action and help clients transform their behavior. Transformative listening describes the repeating process of inquiry that blends primary and secondary listening approaches and tends to transform client perspectives and behavior. Conversely, transactional listening describes a listening approach appropriate for the negotiation and execution of agreements in the transaction of routine business. Self-awareness and use of self foster sensitivity to client needs and practitioner agility in blending the listening approaches used in transformative listening.