This is a study of 10 adults participating in one-to-one mentoring and/or coaching. Participants were selected for interviewing through a purposive sampling process from leading international mentoring and coaching organizations. Selection criteria included (a) being an adult, (b) participating in a dyadic learning, and (c) regarding that relationship as a successful. The study revealed five major themes to be indicative of the processes that promote learning. These themes are (a) learner-orientation, (b) openness, (c) exemplifying, (d) friendship, and (e) trust. The results of this study indicate that the essence of the learning experience is one of guided self-determination fostered by a sense of security and freedom. The ability to openly express one's views unhampered by fear or negative consequences is essential for the learning process to be successful. Unique to this study is the finding that learning one-to-one occurs best when a true friendship exists. Confidentiality should be high, and the atmosphere should be relaxed, for example, with a cup of coffee.