How do leaders make decisions when faced with complexity of organizational life? When leaders are called to exercise judgement how do they know what to do? This chapter uses learning theory to explore how leaders develop a set of guiding principles that are used when making judgements. The focus here is on daily decisions about action, on acts of leading undertaken by people in hierarchical organizational leadership positions. Well established theories from the fields of adult, management and leadership learn-ing are drawn on in order to develop theoretical understandings of how leaders decide what is best to do in a given situation. One core question that will be explored is whether the decisions by organizational leaders are purely instinctive responses, a form of practical coping, or whether they are in fact influenced by a set of tacitly held and developed values or principles.