This paper presents a role-play exercise and assignment that provides an active learning experience related to the system investigation phase of an SDLC. Whether using waterfall or agile approaches, the first SDLC step usually involves system investigation activities, including problem identification, feasibility study, cost-benefit analysis, and preliminary project planning. These topics are normally covered during business-oriented introductory information systems courses and in more depth during systems analysis courses. The role-play case has evolved over several iterations since the 1990s, and it grew from a simple in-class exercise with informal discussion to a full-fledged assignment involving project planning and budgeting, utilizing both face-to-face and online collaboration. Specific roles include a CIO, systems analyst, and representatives from three functional business areas. The paper presents these roles, describes and gives examples of student deliverables, and discusses experiences and lessons learned using the exercise in an IS course.