This study explores the experiences of leaders who have led organisations and teams through an extended period of crisis management whilst completing a UK work-based master’s programme. This paper examines contemporary approaches to work-based learning and explores the effect of organisational and workforce demands in a volatile era of global economic uncertainty. Theoretical and conceptual foundations relating to experiential learning, digital education and communities of learning are analysed and discussed. Taking an inductive qualitative approach, the study analyses semi-structured questionnaire data from senior leaders. The widespread adoption of technology exposes challenges to facilitation and the academic-employer interface, impacting upon learning communities and knowledge exchange opportunities. The findings also suggest enhanced leaders’ adaptive traits, including confidence and self-reliance. This study illuminates critical issues associated with contemporary work-based learning, specifically relating to prolonged macro uncertainty and the effect upon workplaces as sites of knowledge and learning, and risks to dynamic relationships between the psychosocial work environment, genuine opportunities to learn and learner well-being. This work seeks to inform the design of future programs, specifically in terms developing inter and intra-organisational communities of learning and knowledge exchange to enhance best practice and inculcate crucial leadership skills.