The crisis of educational leadership has motivated so much debate and research in recent times in the field of educational administration. Most school leaders have not been trained in the art of educational management and leadership. It has been presumed that anyone who receives a bachelor’s degree in education or a postgraduate diploma in education through training can automatically become a head teacher or principal. That explains why in developing as well as developed countries, school managers and leaders face a lot of challenges. This article seeks to create a link between the career development of senior leadership and the different models proposed by scholars like Day and Bakioglu, Gronn, Wakins and Robbins. The researchers hope to develop strategies that can groom educational managers to assume senior leadership positions. The most influential agents of socialization by Lenka and Vandana, Gupta, Krishnan, Homan & Youngman and Ebot Ashu that enhance educational leadership development have been explored to give this work some serious focus. The primary agent of socialization considered here is the family which is the nucleus of society. The secondary agents of socialization include the schools, peer groups, the churches, work groups, communities, mass medium, social groups and the government. Focusing on Watkins’ seven seismic shifts that transit from specialist to generalist, analyst to the integrator, tactician to strategist, bricklayer to architect, problem solver to agenda setter, warrior to diplomat and supporting cast member to lead role, the researchers argue that school managers can transit to the level of senior leaders and continue to influence school administration in many positive ways. Educational leaders should take their ongoing career development seriously if they are to become relevant in contemporary society. The methodology used in this work is very apt. Based on the field experiences of school administrators, the researchers are able to arrive at findings that support the literature that has been gathered. They are able to explore the career life of educational leaders and identify factors which influence them to become senior leaders and move on as encompassed in the first three phases of Gronn’s and Ribbins’ models, with exceptional three new sub-phases within the accession phase. In all, the study agrees with the general principles of Ribbins’ model rather than the previous work of Day & Bakioglu’s and Gronn’s, who suggest disenchantment and divestiture as inevitable final phases in the career lives of senior leaders. Therefore, Ribbins’ theoretical frame-work of education leadership can be useful in interpreting the link between the career developments of contemporary senior leaders. This study concludes that socialization occurs throughout our life, but some of the most important socialization that occurs during that phase of our lives is the family, school, peers, church, mass media, community, workplace and social group. Therefore, Watkins’ contributions to administration, management and leadership can be used to educate contemporary educational managers and senior leaders in contemporary society.