Collaboration has become a dominant mode of scientific inquiry, and good collaborative processes are important for ensuring scientific quality and productivity. Often the participants in these collaborations are not collocated, yet distance introduces challenges. There remains a need for evaluative tools that can identify potential collaboration problems early and provide strategies for managing and addressing collaboration issues. This paper introduces a new research and diagnostic tool, the Collaboration Success Wizard (CSW), and provides two case studies of its use in evaluating ongoing collaborative projects in the health sciences. The CSW is designed both to validate and refine existing theory about the factors that encourage successful collaboration and to promote good collaborative practices in geographically distributed team-based scientific projects. These cases demonstrate that the CSW can promote reflection and positive change in collaborative science.