A leadership development system (LDS) encompasses all methods and practices used in an organisation to train and develop effective leadership. However, the underlying assumptions upon which such a system is based are often overlooked, and the workplace as a learning site is generally under-investigated, which may cause an unreflected LDS. Using a social representations theory approach, this study explores such underlying assumptions, i.e. social representations of leadership and leadership development, among 19 employees of an organisation with a non-hierarchical business structure. To collect data, the free association method was used to reveal underlying social representations shaping the company’s current LDS. Through a transdisciplinary framing and customised design of work-integrated learning (WIL) among the employees (N = 57), the study also develops an exploratory model for facilitating the development of a deliberate LDS. The results show that uncovering social representations supports professional learning in work, which helps create an LDS that is based on articulated awareness. The study further shows that the process of uncovering hidden values, ideas, and perspectives can support a context-relevant and customised WIL curriculum for professional learning and cultivate a deliberate and purposeful approach to leadership development.