This research study explores the intersection of school leadership and ethics. This study used the hermeneutic phenomenological approach described by Max Van Manen (1990, 2014) to explore the question: How do school leaders experience ethical dilemmas in their role as school leaders? Hermeneutic phenomenology seeks to find the meaning of a phenomenon, which in this case is the experience of an ethical dilemma. Hermeneutic refers to the interpretive-reflective-analytical component and phenomenological refers to the descriptive concrete life-experience phenomenon component (Creswell, 2007; Van Manen, 1990, 2014; Vagle, 2014). This study looked at experiences recounted by four practicing school leaders and found that the experience of an ethical dilemma involves contemplating (cognition) the uncertainty (chance) about the moral merit (values conflict) of a situation and ones capacity (power) and opportunity (options) to act in response. The lived experience themes of time and being watched were also found to be of particular relevance. These hermeneutic themes were drawn from experiences that the school leaders who participated in the study shared during rounds of conversational and analytical interviews. 'Lived experience is the starting point and the end point of phenomenological research....[which] is to transform lived experience into a textual expression of its essence' (Van Manen 1990, p 36). The experiences include experiences of ethical dilemmas regarding student behavior, teacher supervision, program changes, decisions that other school leaders make, parents, and complex systems with multiple actors.