There is no school administrators' pre-service training in the CIS (Former USSR) countries. As for the in-service training, it has been traditionally focused on educational management. As a result, schools in the CIS countries are run as well-oiled machines but there is a big question mark over whether these machines are running in the right directions. Doing things right implies certain beliefs by school administrators about what is "good and bad" in education. However while in their everyday lives educational decision makers are confronted by ethical dilemmas, there is little or no attention at all to these issues in the system of their training. There is an assumption that it is an impossible goal to influence and change their values and attitudes. After some 30 years of continuous attempts to challenge this assumption one should admit that it is indeed a very difficult goal to achieve. Through research, this author has identified seven ethical dilemmas faced by school administrators in the region. Responding to these ethical dilemmas is still the key challenge of democratic educational leadership in the CIS countries.