Critical Action Learning (CAL) involves a deliberate choice to engage with emotions and power relations generated by people's attempts to learn. This choice recognizes that there are likely to be implicit limits to learning in organizations, especially where such learning starts to undermine established ways of thinking and working. One way to manage the demands of engaging with underlying emotions and power relations is to utilize shadow facilitation as a method for facilitator reflection and action. Shadow facilitation is the process through which CAL facilitators work with an experienced, independent other to reflect on their interventions within an action learning set. The role of the shadow facilitator is to listen for the emotions and power relations that emerge from reflection and to offer them back as information to support the facilitation of organizing insight. In this paper we present and illustrate the main ideas that inform shadow facilitation and reflect on the possibilities and limitations of this method for generating organizing insight. We argue that the value of shadow facilitation is that it helps CAL facilitators to work directly on the intense emotions and complex power relations embedded in and evoked by the facilitation role.