The (re-)insurance industry is undergoing significant transformation driven by technological innovations, shifting customer needs, increasing regulatory requirements, and climate change. Companies must constantly adapt to remain competitive. However, many are facing unexpected challenges during transformations initiated in recent years. Especially in the middle of transformative processes, initial enthusiasm might wane, while the benefits are not yet fully realized, and skepticism arises. In this challenging phase, a critical factor is how leaders support their organizations adapting to the changes. Ambidextrous Leadership, or the ability to manage both exploratory and exploitative activities, can be a key tool in balancing the maintenance of proven practices with the exploration of new paths for innovation. This article examines the challenges that arise during mid-transformation processes and how Ambidextrous Leadership can help foster sustainable change.