At some point in time a company’s leadership changes. The individual serving as CEO and Chairman relinquishes the CEO role and passes this on to the next generation, but he or she remains as the Chairman of the Board. Since this individual is no longer an employee of the company, how should he or she be compensated? This is a tricky issue and one that needs careful thought and actions that are consistent with the needs of the company and the individual. This paper provides a summary of the prevalence of this practice, and what has been critical to successful transition.