This study revisits the term “artist-educator”, which was first conceived in the nineteenth century to describe the professionally distinct roles of artist and pedagogue. Since then, this double-barrelled identity has become a default notion among performers in the field of education, which embraces personal philosophy, professional practice, educational experience and teaching methods. As research rarely articulates the distinctive pedagogical approaches among veteran conductors, this study highlights characteristics of professional knowledge of one artist-educator in the field of conducting and orchestral music-making, Maestro Lim Yau. In the being as a Cultural Medallion recipient in Singapore, Lim Yau embodies traits of a veteran artist-educator. Data collected through qualitative methods of semi-structured interviews and observations with the Maestro and his students at NAFA were analysed thematically to present dimensions that extend Shulman’s perspectives of pedagogical content knowledge, including principled practical knowledge and personal practical knowledge. The insights shed light on idiosyncratic tenets that define a conductor’s pedagogical signature, manifested through cumulative musical and life experiences, philosophical principles underpinning his musical beliefs and skilled approaches to relational listening, aural visualisation, risk-taking, reflection and an awareness of the aesthetic potential of sound. Examining the hallmarks of a pioneering artist-educator in Singapore, this chapter celebrates a dynamic relationship between a conductor and his students, revealing an in-between identity that bridges the chasm between a traditional professor of the arts and a practitioner who teaches in the conservatoire.