The objective of this study is to investigate whether teams are more engaged and productive when led by an optimistic manager. Furthermore, we hypothesize that optimistic managers embody positive leadership—employing a strengths-based approach, maintaining a positive perspective, and frequently providing recognition and encouragement—which increases the engagement and productivity of their employees. In a cross-sectional study of 86 employees and 17 managers in an Information Technology (IT) organization, positive leadership correlated with employee optimism, engagement, and project performance. When we looked at a subset of this data prospectively, with 39 employees and 14 managers, manager optimism predicted project performance. Our data support the claim that positive leadership is correlated with employee engagement and performance, and further extends the importance of optimism in the workplace.