The Gordian Knot of Practicing Digital Transformation: Coping with Emergent Paradoxes in Ambidextrous Organizing Structures*

Despite increasing scholarly attention on digital transformation, there are only limited micro‐level insights into how incumbent firms organize and manage their digital transformation efforts on a daily basis. Through a longitudinal, exploratory qualitative case study of a large firm, this article investigates how organizational members respond to an ambidextrous organizing model designed to accelerate digital innovations. The firm relied on a hybrid model of separation and integration to organize and manage its digital transformation efforts. This study unfolds the implications and consequences of such a model at the micro‐level. By applying a paradox lens, it shows how the coping actions of organizational members affected the digital transformation. The article illustrates how the hybrid organizing model led to the emergence of three paradoxes at the organizational level (paradoxes of organizing, attention, and knowledge sharing) that organizational members had to cope with. It shows how organizational members, through their coping with these paradoxes, indirectly affected the organizing model by altering its original design; and how the management, influenced by these learnings, subsequently adapted the model to enable a better sustainability over time. Overall, the findings show and explain why organizing for digital transformation is a particularly complex and paradoxical endeavor. They also provide important insights to managers and organizational developers, helping them to become aware of possible tensions in their organizing efforts as well as of coping strategies and practices to tackle these tensions. Finally, the article suggests different paths for further research in digital transformation and digital innovation from a micro‐level perspective.