The dichotomy of humility and hubris among participants in Executive Education courses presents faculty with a source of heterogeneity not disclosed through the common descriptive statistics of sex, age, education and employment. This article discusses the impact of this dichotomy on the design and delivery of effective executive education. In this domain, a premium is charged and the value of collective learning experiences is often promoted. The authors reflect on the value created from offering blended learning experiences to executives over the last decade. Attention is paid to which components can be delivered effectively through web-based course management systems (CMS) and which components need to be delivered through conventional face-to-face delivery. Particular attention is paid to the dichotomy of humility and hubris among participants. Humility is often found to be masked in an online experience while hubris can emerge with consequences to effective cohort learning. The latter is also more obvious in face-to-face delivery where it can, perhaps, be better managed. However, experience has shown that is not always so easily managed in in-house programs. Recommendations are made to enhance design and delivery that accounts for the humility and hubris dichotomy.