The purpose of this qualitative, grounded theory study was to understand the relationship between positive psychology coaching and thriving in the workplace. Thriving was defined as a marked sense of learning, vitality, energy, and connectivity to others and the work, and positive psychology coaches included coaches who are trained in strengths-based, appreciative, co-active, and positive psychology coaching methods. Twenty people who had participated in positive psychology coaching as a method for achieving change in attitudes, behaviors, or skills were interviewed to understand the key activities of the coaching process that contribute to thriving as well as to understand the individual outcomes of thriving and how they contribute to emotional well-being and vitality. Data analysis indicated a need to revise the definition of thriving since coachees did not distinguish between states of vitality and energy and thriving is more temporal than originally predicted. Other findings revealed that positive psychology coaches utilized strengths-based assessments and activities to help coachees learn how to identify, use, and regulate their strengths, the results of which led to three types of transformation. Coachees experienced personal transformation in their connectivity to others and their work by making personal changes in themselves and how they interacted with others. Physical transformation occurred as coachees learned to recognize changes in their bodies, energy levels, and state of flow. Emotional transformation occurred as coachees changed their self-perception, self-worth, and self-efficacy. As they changed their self-concepts, coachees were able to reframe their attitudes and thinking, become more resilient, and change their careers to align their work with their values and strengths. This study is unique in that it is the first to investigate positive psychology coaching and thriving, and it did so from the coachees’ perspective, which is seldom investigated. Understanding how coachees transform, the processes that enable transformation to occur, and the outcomes that are possible is important since organizations are investing significant resources in coaching and human development processes. Finally, positive psychology coaching is a change methodology coachees can use to create sustainable change that enhances their well-being, relationships, and careers—all factors that can lead to personal fulfillment.