Organizations are unique in their cultures, and paths to gender equality may vary depending on context. The necessary solution for gender equality, therefore, may rely on the opportunities to provide organizations with contextualized insights into the dynamic barriers specific to that workplace, and the ability of that organization to identify creative and evidence-based solutions so that everyone can thrive in a dynamic context. This chapter presents the SOLL Model (The Service-, Operational, and Lecture Learning Model) as a guide for how to facilitate contextualized insights into barriers towards equality in the workplace. SOLL stresses the importance of content learning, skills practice and skill application through service-learning to facilitate thoughtful awareness of problems and credible mastery of relevant skills. Service-learning benefits include reduced stereotypes, increased 140capacity for diversity and increased sense of social responsibility. Although designed for academic contexts, the current work is the first initiative to translate SOLL into an applied organizational learning method.