The arts industry in Singapore is still young and developing, and thus has yet to experience massive shifts in leadership. As new generations enter the scene and the inevitable threshold for retirement approaches, it is critical that companies plan for succession. This research seeks to understand how theatre companies that have undergone leadership renewal or succession planning prepare for and move forward during the transition. The research covers critical points in understanding the types of leadership and models of succession planning, and discusses the experiences of several Singaporean theatre companies. This study is conducted through the lens of understanding succession planning as a social phenomenon, which can be done in many ways and must take into account the nuances and social complexities of the arts industry. The research concludes that although succession planning is rare, there are instances where it does happen. It also finds several factors that can contribute to the success of a succession plan which include: establishing a dual leadership model system, creating development and residency programmes, ensuring that employees and successors have a strong connection to the vision, culture, values and ethos of a company and lastly, holding more conversations about succession planning between arts leaders in the scene in order to create a better reception to the notion of succession planning.