How do educators become successful leaders? This qualitative study set out to learn more about The Lookstein Center ELAI program as well as mentoring and leadership training in general, with the hope of offering insights to other school leadership programs. The mentor-mentee relationship was seen to develop into a collaborative partnership, with the reflective relationships becoming enriching for both the mentor and mentee. The findings also emphasize the value of mentoring for midcareer educators. In addition, the importance of the cohort experience was stressed. Finally, unique to the ELAI program, location was viewed as a very influential aspect of this leadership training program for Jewish educators.