This paper presents findings of a study that examined the effectiveness of a New York City mentoring program in meeting the needs of first-year principals. Data were derived from: (1) a survey of 44 out of 109 new elementary school principals who participated in the Bank Street College of Education mentoring program in New York City; (2) a focus group interview with four elementary school principals who described their mentoring experiences as helpful; (3) in-depth interviews with five elementary school principals who reported positive mentoring experiences; and (4) interviews with Bank Street College personnel. A majority of the new principals reported that mentoring was a helpful experience. Factors that affected program productivity centered on structure and mentor characteristics. Structural considerations included scheduling, site, group size, confidentiality, and agenda. A helpful mentor possessed knowledge of the school system had experience as an administrator and superintendent, and was resourceful, accessible, and trustworthy. (Contains 88 references.) (LMI)