It is appropriate for the IS field to examine the suitability of its practices in light of the complexity of developing electronic business systems. Research shows that planning and developing business-tobusiness electronic trading systems (ETS) is fraught with difficulties concerning the priorities and power of individual organisations. This paper evaluates the usefulness of Triple Loop Learning in managing the diversity associated with planning such systems. The study concludes that approaches associated with Triple Loop Learning can offer insight for managing inter-organisational complexities. The authors propose that such approaches could enhance planning methods for electronic trading systems.