Transformational leadership has been widely researched and associated with followers' performance, attitudes, health and well-being. However, less research has focused on the antecedents of transformational leadership behaviors. A few studies have examined the characteristics of followers and the attitudes of transformational leaders themselves. There is, however, a lack of knowledge on how the context may encourage transformational leadership behaviors. A study of 58 middle managers from two companies in Denmark; a private accountancy firm and a public elderly care explored this. Using the Experience Sampling Method and questionnaires it was found that both situational factors and working conditions were associated with transformational leadership behaviors at work. The results suggest that research strategies using multiple levels and methods can provide additional information on the antecedents of transformational leadership behaviors in middle managers.