Healthcare can be characterized as a complex adaptive system. New Zealand is recognized as having one of the highest rates of enmeshed clinical information and communication technology within this complex system. This paper describes the implementation of an integrated series of electronic clinical health knowledge management systems in a large New Zealand District Health Board. In combination with standard project management, the core implementation team utilized an action research reflective learning approach to enhance their capability to cope with emergent issues, and plan for each subsequent project stage. The emergent focus on “process” issues of connectedness, competency, and control were not the “technical” concerns the principal author was initially expecting, but can be understood through an appreciation of individual and group dynamics, system and complexity theories. In particular, mutual empathy for both self and others was identified as a core capability requirement to cope with the inherent ambiguity within complex systems.