Leonard Bernstein’s New York Philharmonic Young People’s Concerts have served as an exemplar of classical music outreach and engagement for over six decades. The purpose of this study is to update the Bernstein model in new and different ways, both via broader examination of supporting literature in the fields of education, music, arts and religion and, through a more personal approach to the style, technique and spirit of the ambassador of classical music. Three singular research questions present the topic of classical music engagement as discrete from or at least an addition to previous research on entertainment, audience attraction, marketing or education and focuses particularly on how orchestras can better engage any audience in any type of performance. Through action research and self-study methodology, four case studies are presented with analysis of the process, product and audience response to classical music and specifically the producing/conducting/narration/and audience presentation by the author via live concert, video recorded and live stream formats. Through clear quantitative and rich qualitative data collected via online audience surveys after each concert/presentation, key factors of engagement were uncovered that can be applied not only to other classical music concerts but as well to education, other arts, entertainment or sports industries interested in creating a deeper level of participant engagement. The author’s self-examination and growth through the series of case studies reveal a way in which music directors, assistant conductors, and any other leaders who wish to connect with their communities can also approach and refine the art and technique of engagement.