As a scientific and professional discipline, the design of enterprise systems has undergone an impressive development. Today, it has achieved a well-established practice with clearly defined phases, tasks and methods. However, enterprises are challenged by increased complexity in their operations, externally imposed uncertainties and even unforeseeable events. Dynamic global operations call for speedy and effective responses to change. As a consequence, enterprises are challenged to adopt new approaches.In view of this call for probing new roads, it seems useful to examine the roots of design in an effort to re-interpret many of the original ideas. In this paper, we shall briefly study significant contributions to decision-making, systems theory, project management, behavioral science and organization theory, as well as business aspects.To further understand the nature of design, we shall discuss key features, such as purposeful intent based on a stakeholder approach, situational approach, integration of subsystems, perspectives and time horizons, the design process, and modeling.Recent developments, e.g. in design science, design thinking, managing as designing, participatory design, and agile project management, have provided a number of new approaches that in many ways represent answers to the challenges of increased uncertainty and complexity. This has led to the development of seven propositions:∙ Understanding mutual interplay of actors – unveiling self-sustaining informal learning processes∙ Involving stakeholders – clarifying who wants to see the design succeed∙ Accepting diversity – working with several perspectives in parallel∙ Experimenting with new ideas – establishing a playful and creative mood among participants∙ Enacting key features of new systems design – involving users in testing a series of prototypes∙ Including the organizational context – orchestrating a design effort in view of simultaneous development initiatives and top management’s shifting agenda∙ Acknowledging that the intentions of an enterprise information system are realized through people – An enterprise information system only sets the stage for organizational processes.If adopted in an enterprise, management will be challenged to carry out design activities in a radically different way.