The field of special education continually laments teacher turnover and attrition. Special education teachers across all career phases, novice to veteran, describe being overwhelmed by heavy caseloads and too much paperwork, as well as having a lack of planning time for themselves and with general education colleagues. Of major concern to many special education teachers is their frustration over role expectations and a misunderstanding of special education law from their building administrators. Some teachers report these concerns force them to leave the field early. It does not have to be that way. Borrowing strategies from the fields of business and healthcare, special educators can establish a relationship with their administrators that can help both parties avoid misunderstandings and support special education teacher job expectations. The earlier teachers build a relationship, the sooner they will be able to self-advocate for themselves and the services of students with disabilities more effectively.