Health coaching may improve the health of patients with chronic conditions, and the model is growing in popularity. However, little is known about the experience of becoming a Health Coach. We explored our experiences as medical assistants moving into new roles as health coaches, a trainer of health coaches, and their supporting team. A focus group was conducted in November 2012 with three health coaches and one health coach trainer. Using participatory methods, our whole team, including the health coaches, took part in data analysis. We found that learning to become a Health Coach required embracing a radically new role and "unlearning" old ways of thinking, which is transformative but also at times uncomfortable. In our new role as health coaches, in contrast to our work as medical assistants, we work to meet patients "where they are at," and we are more focused on the needs of the patient, rather than the needs of the clinician. Health coaching is emotionally intensive; as health coaches we need robust emotional and instrumental support in our new role. Organizations training Health Coaches should be aware of the dramatic shift in perspective that this new role requires and the support that is needed to help medical assistants as they move into this new role.