Attracting and retaining highly qualified school leaders is becoming increasingly important in our nation. The purpose of this study was to identify factors that motivate or inhibit practicing teachers from seeking administrative positions. Using exploratory factor analysis, survey responses of 329 students enrolled in Master of School Administration programs were analyzed. The findings indicated that factors such as "Challenge, Altruism, Personal/Professional Benefit/Gain", and "Leadership Influence" motivate teachers to transition into administration, whereas factors such as "Insufficient Gain/Personal Benefit, Personal Needs/Issues", and "Increased Risk" inhibit teachers from becoming administrators. Conclusions and implications of these findings were examined. (Contains 3 tables and 2 figures.)