Abstract: Organizations, as a whole, have traditionally faced serious challenges and have incurred tremendous costs in recruiting, motivating, and retaining employees. The retention literature outlines seven major themes of factors that contribute to employees staying with a company. Motivation theory has also been applied to work settings and provides business examples of different motivators for employees. Furthermore, Enneagram theory may provide additional insights into what contributes to different employees’ joining, staying with, or leaving organizations. This study used an online survey of International Enneagram Association members and affiliates to evaluate various hypotheses around differences in employment-related decisions to join, stay with, or leave an organization being explained by differences in Enneagram type.