Understanding how a new piece of technology fits into a user’s working environment is perhaps the classic definition of human factors or ergonomics — a view which fails to address the role of the organization in optimizing this fit. This paper presents a framework which tries to address this failure. The framework (the Dynamic Dilemmas model) is dynamic in that components of the framework are responding in real time to the behavior of other components — over and above any natural tendency they may have to develop and change on their own. And it is dilemma-based in that each component has its own needs and limits, not all of which can be met simultaneously, creating tricky choices concerning accommodation and optimization. In this framework traditional usability is a part of a complex process optimizing the three-way fit between people, technology and organizations, with the fit being assessed in relation to the activities, skills, limits, needs, philosophy and whims of the people, technology and organization.