The development of managerial expertise is a combination of acquiring further knowledge and integrating it with past experience and beliefs. To do so in isolation limits the potential for positive outcomes in one’s management development. Peer coaching is one experiential learning method that can be used to enhance the depth of learning in managerial education. In this chapter, the experiences of 43 students who participated in a peer-coaching program as part of their post-graduate management education are revealed. Powerful learning effects are reported as well as characteristics of successful peer-coaching relationships.