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In this paper, we expand upon our use of the cocoon metaphor for understanding and working with organizations from a psychodynamic perspective. Conceived as both defensive and generative, cocoons are relational phenomena that manifest throughout organizations and risk being mistaken as dysfunctional entities in need of dismantling. To illustrate the utility of the cocoon metaphor in conceptualizing organizational problems, we present a case study of a hospital restructuring following its acquisition by a for-profit health care system and driven by efficiency and cost-savings. The resulting disruptions across operating divisions created a set of problems that necessitated the help of an outside consultant. Engaging members of the organization in the task of solving their own problems entailed recognizing their (inter)subjective experiences and behaviors as more than just defensive hiding, or aggressive attacking, but also as holding the potential for new ways of working and relating. It also entailed showing leaders how to replace environmental impingement in the form of “looking for mistakes” with what we call, borrowing from Marion Milner (1969), a “waiting watchfulness” that fostered understanding of the emotional world inside, outside, and at the boundaries of cocoons to promote organizational learning and meaningful change.