In post-industrial societies, careers are to a large extent unpredictable. Therefore, individuals are expected to demonstrate more and more self-directedness. Universities in general embrace the idea of developing more self-directedness among their students but mostly fail to create the learning environment needed to foster this. In this article, an explorative and qualitative analysis is given of underlying innovation processes in three university departments that successfully implemented a careers guidance programme based on non-traditional (i.e. narrative) methods. We argue that for a successful implementation "collective learning" of teachers is essential, while on a management level "transformational leadership" is necessary to support the collective learning process of teachers. First, the connections between collective learning and transformational leadership are studied. Second, by combining the results of all three cases, we explore what daily practices constitute collective learning and transformational leadership. The study aims to contribute in an explorative and descriptive way to the extant literature, by mapping the variety and richness of the concepts collective learning and transformational leadership as they pertain to realising strong career-learning environments in higher education.