Asymmetrical power relations, imposition and hierarchy characterize much of the field of development. Design and decisions are often dominated by the few as programs determine what is best for the local communities they seek to assist (Cooke & Kothari, 2001). The multiply wounded nation of Nicaragua is no exception to the norm, and the country has a long history of outside intervention by non-governmental and governmental organizations seeking to distribute materials or empower communities. Originally founded through a partnership between the University of Pennsylvania's Graduate School of Education and a Nicaragua Corporate Social Responsibility Division, the Digital Seeds Program strives to push against the common impositional and assistencialist approaches to development through a collaborative, relational and holistic approach. Relational trust and authentic dialogue are centerpieces of what the Program calls accompaniment, or the direct, personalized support of educational actors inside and outside the classroom, and it is within these interpersonal encounters that Digital Seeds' facilitators join teachers in their daily lives. Informed by over six years of participant-observation and insider-outsider evaluation of the Program from its inception in 2009, this participatory action research project seeks to understand how participants make meaning of Digital Seeds as they understand the nature and role of trust and dialogue in thee iterative construction of the Program. It is my contention that a core group of emotionally intelligent and professionally gifted staff embody this deeply relational and dialogic accompaniment model, and their example serves to show the possibilities of reciprocal vulnerability and mutual trust in cultivating respectful partnerships.