This chapter begins by providing historical context and framing commonalities and differences between 21st-century musician careers and historical realities. It explores concepts of leadership through the theoretical lenses of transformational and shared leadership, and through the metaphorical lenses of musical improvisation, composition and performance. The chapter summarises the research, suggesting potential applications in the career preparation of music students in higher education. It illustrates how a transformational leader in a conducted improvisation ensemble creates both a unified musical structure and form, while highlighting the individual strengths of each musician. The chapter discusses connections between the musical expertise required of conducted improvisation and complementary transformational and shared leadership abilities, shows how the skill sets can provide useful tools addressing the challenges of creating sustainable music careers in the 21st century. The roles of the leader and players along with the creative contrasts and overlaps of composition and improvisation come together to illustrate a process-oriented, intersectional style of leadership and music-making.