Moral dilemmas related to processes of school leadership and management can be linked to a variety of subjects such as time management, human resource management, individual development support and the control and results of various processes at schools. This paper studies dilemmas produced by a necessary and frequently painful choice between two exclusive options. It does this with reference to formal school leaders and a focus on a single aspect of school leadership and management: the processes of leadership and management of organizational learning in schools. The main focus of this study is on situations provoking inner conflicts of motive or conflicts with one's environment, arising from differences which formal school leaders detect between their personal morality and the way they reflect collective consciousness. Such situations usually cause doubts about whether a solution is unambiguously correct when in fact leaders feel that no unambiguously correct solution exists, causing them to choose from options which are more or less unacceptable.