Eventful challenges are intellectually compelling to study, in that they stand out as different from the background of the common everyday practice of leading. Through four case studies, this doctoral thesis focuses on leadership challenges in academia. An analysis of the cases shows that the challenges contain various notions and practices of leading that reach a state of tension or conflict with one another in stressful situations. These tensions are here understood as organisational paradoxes, i.e. problems that cannot be solved but can be lived and led. The findings also suggest that a both/and approach, and the psychoanalytic concept of holding can be helpful in an understanding of leading towards constructive outcomes of these leadership challenges. Thomas Sewerin has 45 years of experience working with teaching and consulting in the field of leadership, team and organizational development. In this doctoral thesis, he links the the learnings from his own business practice with the generous and plentiful world of knowledge and rigour that the university and research offer.