This study examines the potential for educational services by career counselors within administrative relationship domains through a case example. It explores the usefulness of career counseling intervention to facilitate career progress through superintendent-school board relationship difficulties as the superintendent attempts to implement reforms and improve student achievement. Reflections and discussions are used at critical moments during the case study to examine factors that divert the superintendent's attention from instructional matters and career goals by identifying effective community and board relationship strategies while addressing current contextually based relational perspectives facilitating career progress.