Based on literature arguing that risk encourages conservative leadership that supports existing routines and strategies rather than innovations and proactive behaviors, this study focuses on the connection among leadership styles, perceived school productivity, and leaders' perceived risk. Results testify to the moderate levels of role risk that school leaders perceive and the relatively high variance existing among these perceptions. Although perceived risk measures are negatively correlated with transformational leadership and positively correlated with transactional and passive leadership, it appears that under conditions characterized by perceived risk, leaders in effective schools are those who act proactively. Such conduct demonstrates high accountability, since risky circumstances increase the potential for mistakes and, therefore, also the threat that individuals experience.