In this report of a phenomenological study, the co-director of a U.S. early childhood program describes and reflects on the interrelationship of his collaborative work with teachers, staff members' documentation of children's work and school events, and his own professional development activities. The author presents and discusses three events that took place over the course of a year. In the first narrative episode, his recent professional development experience at a program inspired by the Reggio Emilia approach enables him to support a teacher who is feeling discouraged about challenging situations in her classroom. Together they plan an after-school event that engages families in reorganizing parts of the classroom. The second narrative episode centers on the author's documentation of a complex construction made by two children in a new space that was created by the reorganization efforts. The final narrative episode consists primarily of a reflective conversation among the author, the teacher, and two colleagues, during which documentation panels created by the author and the teacher are the basis for collaborative discussion about the events of the preceding two narratives. Each narrative is followed by a discussion and brief analysis. The paper concludes with reflections on resulting insights about collaboration, documentation, and professional development.