This essay concerns the design of transformational executive programs. A transformational program presupposes a change in behavior of the attending executive so that the latter becomes more effective in personal or organizational change. To understand what influences the transformational process three triangular conceptual frameworks (building on the short-term dynamic psychotherapy tradition) are presented: the mental life triangle, the conflict triangle, and the relationships triangle.The first shows that cognitive and emotional processes need to be taken into consideration to create changes in behavior. The second describes the sources of thoughts and feelings that may prompt anxiety and cause defensive reactions prohibiting change and productive use of talents. The third relationships triangle explains how an individual's previous experiences create patterns of response that are repeated throughout life and can become dysfunctional.Five major challenges in program design are also examined: selecting participants; identifying the focal issue on which participants need to work; the creation of a safe transitional space that enables the change process; using the group dynamic to foster transformation and to arrive at internalization of the change process; and the educational implications for faculty, facilitators, and coaches.