This paper is a joint research project by the Jane Glassco Arctic Fellows  which attempts to pinpoint the kinds of learning environments – within the education system and beyond – that best foster the emergence of “leaders” in northern Canada. The Fellows conducted interviews with a total of 20 recognized leaders from all across Canada’s North who live and work in the Yukon, Northwest Territories, Nunavut, Nunavik and Nunatsiavut. Interviewees were asked about their personal educational experiences within the formal school system and informally within their family and community environments, and how these experiences shaped and sharpened their leadership skills.