Digital transformation and the increasing use of Artificial Intelligence are changing how SMEs receive and pass on information and transform it into organisational knowledge. Transparent, recursive, and timely information transfer to decision-relevant stakeholders harbours considerable potential for identifying, making accessible, and collectively utilising existing knowledge within the company. However, these efforts are often hampered by inhibiting factors that cling to traditional methods and limit organisational learning capacity. While some stakeholders hope that digital technologies will relieve experienced knowledge holders of routine tasks and enable them to perform more demanding activities, there are fears of potential knowledge gaps or wrong decisions being uncovered and of losing one’s job through Artificial Intelligence. This raises the question of whether medium-sized companies’ knowledge management can effectively link personal and systemic knowledge, foster organisational learning, and develop strategic competitive advantages. These companies’ communication and management processes provide key entry points for critically analysing knowledge management design. This article examines the specific organisational and process design for communicating information and decision-making in day-to-day operations. Empirical findings from an interdisciplinary literature analysis (n = 177) and a qualitative survey (n = 26) illustrate the organisation in practice. The evaluation includes the prompt and recursive provision of information and managing fears and uncertainties as barriers to organisational learning. Finally, the impact of specific design choices on learning ability is analysed.