In this article I examine the cultural historical context that affects the Russian national character. I refer to the Russian climate, the centuries of social unrest that have troubled the country’s history, the multi-ethnic composition of its citizens, the role of the Orthodox church, the mir, the dramatic fall of Communism and rise of materialism, the insidious “bureaupathology,” and the persistence of “Oblomovism.” I also discuss decision-making practices and power dynamics within Russian organizations, highlighting the difference between authoritarian and authoritative leadership practices and exploring the strengths and weaknesses of the Russian leadership style. I consider Russia’s history of despotic rulers — and its preference for a “managed democracy” — and how the rise of materialism brought many dysfunctionalities, including increased corruption, and (for many citizens) the loss of a moral compass. In the last part of the article I present an agenda for change, making a plea for a new, more innovative, educational paradigm for the younger generation of Russians that focuses on character development (social and emotional learning, moral reasoning, and other important life skills). I make a number of suggestions about the role management education, different organizational designs, and new leadership practices can play in inducing changes in Russian society and make a case for the need for responsible entrepreneurship.