In this conceptual paper, we consider the challenge of managing millennials from two perspectives. We describe the millennial generation as coming of age awash in technology, resulting in a tendency toward what we label complexity avoidance. We then briefly review the findings of others who identified rising levels of narcissism associated with the generation. We turn to Argyris’s (1970) Organizational Development Intervention and Method model to describe how these characteristics present challenges to learning, development, and management in general. We then turn to recommendations for facilitating the learning and development of generationally typical millennials and then for millennials who also possess narcissistic traits.