This study investigates the evolving landscape of learning and innovation within organisations that are particularly affected by the increasing digitalisation and prevalence of remote work and trainings. Focusing on the police and technology sectors, in this research 20 individuals were interviewed, identifying both real-time and long-term challenges associated with remote learning and innovation. In the police sector, the real-time challenges included one-way efficiency, encompassing impracticality, unidimensional learning situations, and efficiency-driven multitasking. A long-term challenge was individualistic performance orientation, suggesting a shift in learning responsibility from the organisation to the individual. In the technology sector, the real-time challenges involved incomplete detections during remote innovation, encompassing missing artefacts, unlikely coincidences, and narrow observations. A long-term challenge was the weakening of social bonds, with subthemes such as community distancing and a decline in social skills. The study emphasises the critical need for appropriate remote workplace pedagogy, community reinforcement and well-planned training to address these challenges, emphasising that the values guiding remote work and virtual environments play a crucial role in shaping learning outcomes.