This paper seeks to explore theoretical concepts that surround the creation of individual guiding principles, or distilled wisdom, used by leaders in the act of leading. It is assumed that leaders develop their own guiding principles which are used when addressing difficult, or ‘wicked’ problems. Personal experience is often cited in the literature as being essential in the development of tacit knowledge and of wisdom (Sternberg, 2003; Yang, 2014; Kuntz & Bamford-Wade, 2013). However, this literature often takes an entitative approach, separating the act from the situation. The paper concludes by suggesting a method of research that seeks to establish how the situation and the individual come together to generate a set of guiding principles or distilled wisdom which a leader can use to deal with future problems.