In Fromm's view, freedom is ambiguous. Humans tend to, rather than using it, avoid its negative effects, particularly uncertainty, and submit to authorities and structures prescribing thoughts and actions. Technological modernisation and digital transformation enhance uncertainties aligned with free societies and new mechanisms of submission through ubiquitous computing, including surveillance, data mining, behavioural manipulation, and decision making by artificial intelligence. As this chapter argues, an anthropological foundation should be required as a core demand for the education of school adminstrators in the context of technological modernisation. While teachers take up the role of junior educational administrators, policy translators and, within the German system, are the sole recruitment base for senior educational leadership positions, traditional educational programmes, comprising philosophical foundations, have been swept away in the name of effectiveness and outcome orientation, and the preparation of these novice educational administrators in recent decades has become dominated by psychological notions of teaching and learning. By excluding other paradigms, particularly by falling short of anthropological foundations, creates a void regarding their knowledge base in a phase of fundamental threats to free societies.