This article is based on the author's autoethnographical research on leading practices of Steiner school principals over a period of major change and crisis in a Steiner school's life. This research included the use of the theory of practice architectures to uncover unsustainable contradictions in Steiner schools which constrain the full promise of the educational approach as an engine room for social change and renewal. These contradictions include doubt and uncertainty about the role of the principal and of leadership itself; and the depth of the emotional load of the principal and teachers in holding the competing ideological and pedagogical tensions of the Steiner and broader educational policy environment. Maintaining the integrity of the higher purposes of Steiner education involves moving away from a leader-centric approach that does not fit well within the Steiner school ethos, to embrace capable, praxis-oriented leading practices which involve intentional hierarchy and healthy collective participation.