This paper utilised a two-part mixed-methodology to examine the value placed on judgement and decision-making by a sample of qualified mountain leaders in the UK. Qualified leaders (N = 331) completed a web-based survey and a smaller sample (N = 8) were then interviewed. Survey data showed that mountain leaders place greater value on their judgements and decision-making when compared to the technical skills of mountain navigation and rope work; however, the process for developing these judgement skills was unclear. Interview data identified that judgement skills appear transferrable from other domains experienced by the leaders (e.g. emergency services, military) but are then recontextualised and modified for effective use within mountain leadership. The leaders facilitated this via a nested reflective process that combines in-action, on-action and on-action/in-context aspects that rely on metacognition. This combination of reflection and metacognition allows for rapid development of judgement making skills in-context. Implications for mountain leadership training are discussed.