The most challenging problems for school leaders are that those which recur and display the characteristics of a leadership dilemma: with tension between a concern for organisational goals and a concern for collegial relationships. A critical competency in school leadership is the ability to manage such dilemmas. To do this, leaders must be able to recognise and articulate dilemmas, reflect critically on their own problem-solving beliefs and actions, and learn skills which enable them to apply strategies which result in positive, lasting solutions. Principals can become aware of defensive approaches which block both personal and organisational learning. They can learn how to make a transition to productive approaches to problem-solving which are the foundation of effective dilemma management.