This article reports on the values and moral dilemmas of one Icelandic headteacher. The article draws on doctoral research currently being conducted with educational leaders in Icelandic basic schools. The research explores the values underpinning the work of female and male educational leaders and how values impact upon their actions, in particular when encountering moral dilemmas. Data were collected from semi-structured interviews with participants who all work in Reykjavik, the capital of Iceland. The main tool of analysis is an adapted version of Begley's "arenas of administration". This article adds another theoretical dimension, that of gender, to Begley's model. Results show that the motivation behind the headteachers' values is primarily based on consensus. They also show how the headteacher attempts to act as a mediator between competing values of the various leadership arenas while coming to terms with her own. Gender was found to effect on the headteacher in various ways as she felt the need to negotiate and contest her values and leadership actions against stakeholders of various arenas. (Contains 1 note.)