Managerial discretion is said to be a fundamental condition for effective leadership. Studies of managerial discretion have to a large degree focused on the magnitude of managers’ discretion and how different factors influence managers’ perceived level of discretion (Hambrick, 2007; Hambrick & Finkelstein, 1987; Hutzschenreuter & Kleindienst, 2013). In this chapter, we argue that it is insufficient to study the size of managers’ room for discretion. We also need to understand the content included in leaders’ discretionary rooms. In a study of ten successful logistics companies, one of which was studied more in-depth, we find that the managers perceive their room for managerial discretion as large. However, the alternatives considered are to a large extent operational and short-term, at the expense of more long-term, strategically relevant alternatives facing future challenges. Hence, we develop the concept “strategically relevant managerial discretion”, which, in addition to the alternatives that managers are aware of and that are acceptable for the mangers’ stakeholders, also includes a new dimension: to what extent the alternatives are strategically relevant for future challenges. We conclude the chapter by pointing out interesting directions for future research, including a call for empirical studies of the conceptual model developed in this chapter.