Recent leadership research has demonstrated a need for better understanding the process of becominga leader because it might be qualitatively different to being a leader. If so, there is likely to be a need for pedagogies designed deliberately to support first-time outdoor leadership experiences and any such pedagogies must be informed by the needs of first-time leaders. Becoming a leader in outdoor educational settings involves moving from the relative equality of being one participant among several in a group to a position of some influence in the group. This paper draws on empirical data from in-depth semi-structured interviews with adult outdoor education (friluftsliv) students in Norway to explore factors influencing initial leadership experiences in a formal educational setting. We found that becoming an outdoor leader involves transformations that can be complicated by the educational setting. We discuss implications for pedagogical approaches to outdoor leadership development in formal education settings.