Although the workforce has become more diverse, there is still a predominance of White men in positions of senior leadership. This is incongruent with social norms and values, evolving population demographics, and political movements (e.g., the MeToo and Black Lives Matter). Further, it suggests that, despite progress in shattering the glass ceiling, there may still be obstacles to senior leader roles for people who vary from the expected demographic profile. Eagly and Carli (2007a) addressed this issue for women by developing the labyrinth metaphor; however, few researchers have explored how the labyrinth and its inherent challenges might apply to others. We strive to broaden the discussion of the labyrinth metaphor, increasing its applicability, by considering two types of labyrinths—unicursal and multicursal. We also deepen the theoretical foundation by positioning the labyrinth metaphor within two prominent organizational perspectives: institutional theory and social identity theory. Relying on arguments culled from these theories, we build a typology consisting of four different categories of challenges—identity, acceptance, access, and expectations—leaders may face on their path to senior leader roles. We then explicate how these challenges create differential paths for individuals who align with the traditional leader prototype and those that do not. We believe that awareness of the underlying mechanisms of the challenges leaders may face will particularly help create solutions to these obstacles faced by individuals who are diverse in gender, race, sexuality, religion, and other important factors.