Empowering leadership is characterized by a decision-making process that entails investing in human capital within the workplace through power-sharing and embracing uncertainty. To better understand the decision-making process of leaders who take risks and foster empowerment among their followers, we draw upon prospect theory and propose that leader perceived organizational support (POS) acts as an antecedent to empowering leadership, subsequently influencing follower outcomes (task performance, Organizational citizenship behavior, and voice). Furthermore, we introduce leaders’ supervisor close monitoring as a boundary condition in this proposed mediation model, as it determines leaders’ autonomy in their leadership decisions. Our results from a time-lagged investigation on 202 leader-follower dyads indicate that when supervisor close monitoring is low, the relationship between leader POS and empowering leadership and the indirect effects of POS on follower outcomes remain negative. This negativity arises from leaders adopting a risk-taking perspective on decision-making when pursuing empowering leadership. Conversely, when supervisor close monitoring is high, the relationship between leader POS and empowering leadership and its indirect effects on follower outcomes becomes positive. This is because high supervisor close monitoring reinforcing the resource utilization when leaders possess high POS, thereby fostering empowering leadership and follower outcomes.