Adaptive expertise, an individual's ability to perform flexibly and innovatively in novel and unstructured situations, could have particular relevance for expedition and outdoor leaders. This element may be recognized in leadership practitioners who are able to act more effectively when problem-solving in complex, ambiguous and unpredictable environments. The authors present a number of perspectives intended to assist individuals in making better use of experience to develop adaptive expertise within their leadership routines. Analysis of the literature suggests that when learning to enhance expertise, individuals benefit from extensive deliberate practice, variation in that practice and reflection on their experiences. Also, adopting proficient thinking can guide reflective processes towards making balanced judgements about how and if an experience may change a leader's current understanding. We provide examples of applying some of the concepts that are relevant to developing adaptive expertise in the context of expeditions, and discuss some of the broader implications of the paper for outdoor leadership. (Contains 3 tables and 1 figure.)