Higher music education institutions play a crucial role in shaping the musicians and music educators of today and tomorrow. Many institutions already employ innovative programmes aimed at broadening students’ horizons; however, few of these programmes are implemented in music-related areas. With a focus on Generation Z – “digital natives” born between 1995 and 2010 – this chapter considers some of the key challenges and constraints on efforts to engage the most recent generation of students in developing and strengthening their leadership capacities in higher music education. Specifically, this chapter focuses on the profile of Generation Z undergraduates based on recent research, the affordances and constraints of Generation Z’s engagement in leadership development, and the development of leadership capacities with Generation Z using an ally or “critical friend” approach. It is argued that through the development of leadership capacities, Generation Z learners gain a sense of direction and the resiliency necessary for negotiating key transitions and transformations associated with today’s fluid, fast-paced and changeable world.