Although the value of directive leadership has been widely recognized, there is a very limited understanding on the antecedents of such leadership behaviors. By integrating adaptive leadership theory and trait-activation theory, we propose that leaders’ directive behaviors are their adaptive outcomes through the interaction with team members: high core self-evaluation (CSE) leaders are more likely to adopt directive leadership behaviors when team collective CSE is lower, but reduce such behaviors when team collective CSE is higher. We further hypothesize a three-way interaction in which team collective CSE and team performance jointly moderate the relationship between leader CSE and directive leadership. Results from a multi-source two-wave field study with 203 leaders and their team members corroborated our hypotheses. Overall, the research illustrates a contingency model of directive leadership’s origins. We advance directive leadership literature by offering new insights into the complex adaptation processes that facilitate or constrain leaders to demonstrate directive leadership.