Cross-cultural managers who are unaware of their stereotypes risk operating from potentially inaccurate and ineffective cognitive platforms, yet there is a need for more education and training approaches in the area of stereotype awareness. Experiential approaches to social learning that have been proposed as holding high effectiveness and dialectic logic provide a specific avenue for altering perceptions. An experiential approach to stereotype awareness is developed with a multicultural group of over 370 participants. Context influenced participant outcomes in stereotype awareness development indicators and was more significant than individual traits. Participant self-efficacy was found to demonstrate a slight positive moderating influence. Stereotype awareness is established as an important trait for cross-cultural managers; the described experiential approach should be considered as a possible avenue in developing greater effectiveness for managers dealing with diverse groups and cultures. Organizations that can better educate and train people in developing personal stereotype awareness stand to ultimately advance effectiveness in cross-cultural and diversity management.