This chapter examines the impact of digitalization on leadership ethics. It moves beyond viewing technology as a mere tool, analyzing it instead through the lens of philosophy of technology, particularly the work of Ernst Cassirer. The discussion highlights how digital technologies shape social practices, redefine possibilities for freedom and autonomy, and can either support or undermine deliberative processes. It argues that in the information age, leadership is best understood as operating within networks where technology and humans are co-actors, making an understanding of these new dynamics essential for contemporary ethics.