Strategic decision-making in organizations, especially in healthcare, faces increasingly complex challenges in the face of rapid technological, demographic, and societal changes. Understanding and anticipating possible futures is crucial to keep organizations resilient and adaptable. While the concept of diegetic prototypes within design fictions has helped to discuss and visualize complex future issues in other fields, their application in the context of ageing and particularly from the perspective of a health insurer is largely unexplored. Tangible future scenarios enable decision-makers to experience potential challenges and opportunities not only intellectually, but also emotionally and practically. In the context of ageing, where demographic changes will have significant implications for healthcare and society at large, the need to make possible scenarios tangible is even more critical. This research has the potential to provide insights into the ways in which speculative design, particularly diegetic prototypes, can enhance strategic decision-making. This is relevant for health insurance executives and boards of directors, as they face the twin challenges of both meeting the current needs of their customers and anticipating and responding to future developments.