This chapter presents the diversity and inclusion efforts of a practitioner tasked with an enormous task: to attend to the social-emotional welfare of students with regards to diversity, equity, and inclusion; mental health; and substance abuse prevention, intervention, and recovery. A detailed history of the position’s development precedes a discussion of the author’s approach to tackling these tough issues through data use, community discussions, learning opportunities, and more. The author describes the challenges – both expected and unexpected – she faced in this journey and ends with outlined advice for school leaders preparing to initiate similar district-wide changes.