Digital Transformation (DT) has become a major focus with the rapid advancement of digital technologies. However, achieving successful digital business transformation (DBT) goes beyond simply implementing new technologies; it requires a strong emphasis on the organisational dynamics and the behaviours of leaders and staff. This paper shares findings from a focus group of nine experts who work as the Enterprise Transformation (ET) team within various organisations. The aim was to explore their lived experien ces regarding organisational behaviour and workplace politics exhibited during DBT, as well as the challenges these behaviours pose to managers. Participants highlighted that disruptive transformations often lead to negative organisational behaviours to sa botage the efforts of the ET team, noting the paradox that high-performing employees are often the most resistant to change. They also observed that the organisation fails to recognise and celebrate the success of the transformation. The experts suggested alternative strategies for successful transformation, arguing that traditional change management approaches — designed to reduce disruption —are not suited to DBT. Furthermore, they recommended starting the transformation with a small, isolated team or depart ment and gradually expanding once success is achieved. A key insight was that executive leaders must be fully committed to the change and adopt a ‘chaos management’ approach, which differs from conventional change management practices. Key propositions are suggested, emphasising that successful digital transformation hinges on addressing aspects of organisational dynamics - leadership, culture, communication, and processes - to navigate the complexities of disruptive digital transformation.