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In the field of global leadership, much of the research has focused on uncovering competencies and methods for assessing competencies. The process of developing global leaders has been researched less frequently; however, it is widely accepted that this process involves learning on the part of the leader. Mezirow’s (1978, 1991) transformative learning is a special type of learning in the domain of adult education and a useful lens to better understand the disorienting triggers that are thought to induce global leadership development (GLD). In simple terms, a disorienting experience occurs when we discover that something we thought was certain is now uncertain. Conducting business in another country or merely navigating to a grocery store or restaurant there can be a disorienting experience. In these situations, people are exposed to new information that does not fit their current meaning structures or thought paradigms, and at this juncture, people have a choice: to transform their perspective or remain unchanged. When individuals transform their perspective, they are experiencing transformative learning. The first section of this chapter reviews the concept of disorienting experiences across disciplines and within the domain of learning and education. The second section explains three GLD process models with a special focus on the role played by disorienting trigger events in each one. The final section explains the Disorientation Index (Ensign, 2019), which articulates dimensions of trigger events. The chapter concludes with future research directions and practical implications.