Due to the radical changes and complexities within academic institutions, leadership development addressed to academic leaders in the digital age has become more critical. In the available literature, the outcome assessment of leadership development and its related factors have not been evaluated rigorously. The current study investigated the contribution of peer interaction and two subscales of motivation to the effectiveness of the leadership development programs perceived by training participants in a diverse context. Of 101 participants, the majority of training workshop attendees were junior and middle-level leaders from both European universities and Chinese universities who participated in the leadership development programs organized under an EU project. PLS-SEM was exploited to validate the measurement model and test the hypotheses. The results showed that self-growth and peer interaction significantly contribute to perceived effectiveness, whereas networking motivator shows nonsignificant impact. The findings also illustrated that the two motivation patterns have significant effects on interaction quality. The mediating role of peer interaction on the relationships between the two motivational factors and perceived effectiveness, respectively, were not found in the current study. The findings contributed to identifying the role of different contributors to the effectiveness of the leadership development program in HE contexts and the potential of such a program to enhance knowledge and capacities of academic leaders regarding university governance and leadership.