After 10 National Championship wins as Musical Director of Brisbane Excelsior Brass Band, the author is often asked several questions: What does a conductor need to know to be successful on the contest stage? What needs to be done to remain at the top of the game for such a long period? What does the author do differently to others? The answers to these questions lie in understanding the various roles of the brass band conductor, and how these roles are realized in the author’s professional practice. There has been very little research done on maintaining the competitive edge over time despite other changeable factors and players. An understanding of the ongoing responsibilities of a musical director may help minimize the impact of socio-cultural changes within the band community following successive wins at a national level or a change of director. This study investigates the role of the musical director by reflecting on the responsibilities and practices of successful directors and analyzing the personal characteristics and interpersonal relationships with band members through autoethnography and interviews with other directors. Attention has also been paid to the administrative support and team dynamics within the Brisbane Excelsior community. For Brisbane Excelsior, the study found that the combination of the musical director’s ongoing self-reflection, consistent methods over 14 years (2002–2016), and intrinsic personal characteristics created an environment where band members strove to succeed, and were challenged to maintain a very high standard of playing.