Social workers are required to become effective boundary spanners to address complex social problems with community-based and cross-system collaboration. However, substantial tensions exist in the literature about how to build successful collaboration, stemming from the massive use of the two competing paradigms: functionalist and critical paradigms. Using a dialectical analysis, this article attempted to uncover and synthesize paradoxical understandings of the major elements of successful collaboration. Significant contradictions between the two contrasting paradigms are identified at the multidimensional levels, including (1) member capacity for developing objective/consensus knowledge vs. subjective/dissensus knowledge, (2) unity vs. diversity in membership, (3) centralized vs. decentralized network governance, and (4) stable/standardized vs. flexible/responsive coordination. The results suggest that there is no consensual approach to developing transformative collaboration that promotes members’ critical capacity, equal relations, democratic governance, and empowering coordination. Social workers should identify and utilize inherent contradictions as a catalyst for developing and maintaining transformative collaboration by considering its dynamic process, context, and interconnection with other systems.