Although transformational learning is widely acknowledged within coaching, little is known about how such learning could be achieved in practice through coaching. Even less is known about how transformation can be achieved within a short period of time. This article reports on research that explores whether transformational shifts in the room can be achieved. The study was conducted using a grounded theory approach with 12 coaches and five clients. Findings demonstrated that transformational shifts evolve over the course of the coaching engagement, rather than happening live in the room. This led to the development of the Evolving Transformational Shift (ETS) model that identifies the interventions that help to increase the possibility of such learning to occur.