Succession literature addressed factors affecting the development of successors’ leadership skills. Yet the role professional advisors play in this process is not well understood. This study contrasts the detailed descriptions of four advisor-directed leadership development processes, to suggest a grounded theory of how advisors can facilitate the construction of successors’ leadership. Adopting an insider–outsider approach to the collection and analysis of ethnographic data, the study revealed that the assumption of a transitional leadership role by advisors—an interim leadership held by the advisor while supporting the successor’s leadership development—was critical to moving the succession process forward.