Whilst adaptive experts have well-researched beliefs and attitudes towards learning, what is unclear are the interactions that occur within the learning environment that constitute their learning experiences. The practice of geriatric medicine emphasises the interdisciplinary care of complex frail older adults. Our study sets out to understand the learning experiences of adaptive experts in geriatric medicine by examining how interactions at the intra-personal, inter-personal and organisational levels contributed to the development of adaptive expertise. We conducted an exploratory qualitative study through semi-structured interviews of 16 geriatricians experts from a tertiary hospital in Singapore. Data were analyzed via reflexive thematic analysis. The core essence of the learning experiences was described as a journey of 'knowing when we do not know', which was characterised by three themes: (i) Anchoring ethos of person-centric care where the experts drew upon their values to develop a holistic view of the patient beyond the medical domain, (ii) Enabling stance of being curious where their curiosity and openness to learning was nurtured through the practice of reflection, and with the benefit of time as a commodity and for development of expertise, and (iii) Scaffolding organisational culture of inquiry where an environment that is supportive of learning is built on the culture of psychological safety and the culture of mentoring. Taken together, our study highlighted the importance of interactions at the intra-personal, inter-personal and organisational levels in the learning experiences of adaptive experts.