In this chapter, the authors emphasize the importance of reflexivity in the ongoing work of challenging assumptions and biases as it relates to helping. They posit that individuals need to consider their positionality in addition to issues of knowledge, language, and power before engaging in meaningful community action. Drawing on a Freirean conceptualization of dialogue, they call for authentic listening and introduce a Model of Critical Dialogic Synergy to illustrate an approach to learning from self and from others that involves reflection, agency, and action.