Individuals high in tolerance of ambiguity (TOA) are comfortable with, desire, and strive to manage ambiguous situations. We predicted leader TOA would be associated with better follower performance outcomes, depending on the level (Study 1) and nature (Study 2) of follower role ambiguity. Data were collected from employees (Study 1, n = 423) and managerial employees (Study 2, n = 326) who rated their leader on three facets of TOA and provided self-reports of their own performance outcomes. Positive implications of leader TOA for follower learning goal orientation and job performance (Study 1) were most pronounced when followers perceived low role ambiguity and, in the prediction of situational coping (Study 2), when ambiguous work situations were categorized as challenges (unexpected events requiring problem-solving) compared to hindrances. Findings have theoretical implications for understanding when TOA in leaders is optimal and have practical relevance for leaders seeking to adapt to the situational needs of their followers.