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This qualitative, exploratory study examines the development and implementation of diversity training in small and mid-size organizations in a Midwestern region of the United States. The results are contrasted with diversity best practices and found lacking in key elements identified as most likely to yield success. Specifically, the organizations in this study did not provide training beyond awareness level, failed to conduct front-end needs assessment, provided little if any in-depth evaluation of diversity training and showed varying support for diversity endeavors from the leadership and through connecting diversity training with other systemic initiatives. The article concludes with recommendations for additional exploration of adapting effective diversity training practices to minimize pitfalls and maximize possibilities in small and mid-size systems.