This basic interpretive qualitative research study explored the personal and professional backgrounds, training experiences, perspectives, and perceptions held by adult volunteers serving as crew advisors in the Venturing program of the Boy Scouts of America (BSA). Venturing is the BSA’s adventure oriented youth development program for coeds age 14-through-20. Upon joining a Venturing crew, youth members are known as Venturers, and the top adult volunteer of the crew is the crew advisor. According to the aims and mission of the BSA, crew advisors are expected to facilitate the positive development of her/his crew’s Venturers, yet an analysis of the basic training provided to crew advisors suggests that skills related to the facilitation of positive youth development are not a part of the training curriculum. In order to identify the knowledge, skills, and attitudes that would support a crew advisor’s ability to facilitate the positive development of the Venturers in her/his crew, primary data were obtained from a three-interview series with five Venturing crew advisors residing in Mid-Atlantic States of the USA who were considered by their peers and by the researcher to be relatively successful at delivering the Venturing program. Other data were obtained by observations of crew advisor trainings and interviews with professionals from other youth organizations responsible for adult volunteer training. Data analysis described four capabilities that appear to be present in relatively successful crew advisors, assessed crew advisors’ willingness and ability to utilize a youth development resource produced outside of the BSA (the 40 Developmental Assets for Adolescents), and a suggested training scheme for preparing adult volunteers for supporting positive youth development within their youth-focused programs and organizations. Ultimately, this research presents suggestions for optimizing the training and preparation of adult volunteers to improve the efficacy of the Venturing program for facilitating the positive youth development of its Venturers. Written as a scholarly personal narrative, the researcher’s personal and professional background, including 23 years of experience as a member and volunteer of the BSA, provided context for the inquiry and a frame of reference for the data analysis.