Kierkegaard, in his description of Don Giovanni (Either-Or) and the concept of seduction, emphasizes the mutuality between seducer and seduced. Both are seduced by desire and subjects to desire. The same goes for charismatic/transformational leadership. This paper offers a comparison between 1) Don Giovanni and 2) Bernhard Bass’ concept of transformational leadership (1996). Transformational leadership creates a mutual atmosphere of trust in which the employee is voluntarily seduced: “voluntarily” as a free subject. The leader’s means to create this trust is by showing respect of others, having coaching skills; exerting responsibility, and facilitating “cognitive team players”. Analyzing these common features through Luhmann 2000), both leader and follower are observing how the other is observing themselves. It is this mutual observation of the other’s observation that creates the seduction. Contemporary ideals of school leadership in Denmark bear strong connotations to this figure of transformational/charismatic leadership (OECD 2007, see also Leithwood 1996). I investigate 22 interviews with Danish head teachers on strategic leadership, relating it to Kierkegaard's Don Giovanni and Bass' notion of transformational leadership.