The authors used a longitudinal design to investigate the relation between leadership behavior and the well-being of subordinates. Well-being is conceptualized as people's feelings about themselves and the settings in which they live and work. Staff members (N = 562) of 2 Community Trusts participated 4 times in a 14-month period. Five models were formulated to answer 2 questions: What is the most likely direction of the relation between leadership and well-being, and what is the time frame of this relation? The model with the best fit suggested that leadership behavior and subordinate responses are linked in a feedback loop. Leadership behavior at Time 1 influenced leadership behavior at Time 4. Subordinate well-being at Time 2 synchronously influenced leadership behavior at Time 2. Leadership behavior at Time 4 synchronously influenced subordinate well-being at Time 4.