Work organisations face demanding challenges, such as expectations to be creative, innovative, agile, competitive, efficient and adept at using employees’ knowledge while understanding and taking care of employees’ wellbeing. Organisations are actively implementing new ICT systems and environments because they seem to increase the effectiveness of interaction and collaboration, workplace learning and work performance. Employees are expected to learn and to innovate continuously. Thus, managers often need to be social acrobats, combining basic tasks, managing projects and creating and meeting innovative goals. Work units may be potential and versatile learning and development spaces, but at the same time, existing routines, traditions and power relations in organisations create different kinds of boundaries and conflicts. Dialogic leadership might be one of the key factors in successful modern organisations. Dialogic leadership is a prerequisite to meeting the challenges mentioned above. In this paper, we examine the potential and challenges of dialogic leadership and learning when adopting and using e-Calendar (eC) in one of the Dinno programme’s professional case organisations.