Storytelling in leadership research is usually approached positively and seen as a non-problematic resource or even a “tool” for leadership purposes. However, using stories and narratives involves challenges for leaders. Storytelling may result in intended outcomes, but it also carries a risk for undesirable leadership consequences. In the storytelling approach, there is a hidden assumption that listeners are homogeneous and that they are not critical or active. Empirical studies rarely approach failed storytelling experienced by leaders: the feelings of failure, reasons, and consequences. In this chapter, we focus on the risky nature of leadership storytelling as well as the element of learning to be a better leader inherent in it. Based on empirical qualitative data, we apply thematic and content analysis on interviews from 13 leaders. Based on the findings, we present the following five special dimensions/themes of failure, illustrating the risks involved in leadership storytelling: (a) diversity of the audience, (b) situation/context, (c) loss of authority, (d) storytelling skills, and (e) audience misinterpretation. We interpret the findings in the context of the leaders’ personal experiences, their meaning for the leaders’ self-reflection, and the leaders’ leadership learning for the future. Moreover, we discuss these dimensions from the perspective of diversity and the hidden assumption in the storytelling approach that the listeners are a homogeneous group.