Using a field experiment in the United Arab Emirates, we compared the impact of directive versus empowering leadership on customer-rated core task proficiency and proactive behaviors. Results demonstrated that both directive and empowering leadership improved work unit core task proficiency, but only empowering leadership improved proactive behaviors. Examination of boundary conditions revealed that directive leadership improved proactive behaviors for work units that were highly satisfied with their leaders, whereas empowering leadership had stronger effects on both core task proficiency and proactive behaviors for work units that were less satisfied with their leaders. We discuss implications for both theory and practice.