The Human-Computer Interaction Laboratory (HCIL) and the Maryland Department of Juvenile Justice (DJJ) have been working together to develop the ProgramFinder, a tool for choosing programs for a troubled youth from drug rehabilitation cente rs to secure residential facilities. The seemingly straightforward journey of t he ProgramFinder from an existing user interface technique to a product design r equired the development of five different prototypes which involved user interfa ce design, prototype implementation, and selecting search criterion. While HCIL 's effort focused primarily on design and implementation, DJJ's attribute select ion process was the most time consuming and difficult task. We also found that a direct link to DJJ's workflow was needed in the prototypes to generate the nec essary "buy-in". This paper analyzes the interaction between the efforts of HCI L and DJJ and the amount of "buy-in" by DJJ staff and management. Lesson learne d are presented for developers.