For approximately three years, the Chicago Public School (CPS) district has been undergoing a process of creating protocols, structures, and tools that will assist schools with the implementation of multi-tiered systems of support (MTSS). An on-going area of development for the district as well as for my school is developing teachers' abilities to support all students in the leveled tiers, particularly Tier 3. The purpose of this self-study is to understand, document, and analyze my actions (as the principal) while implementing MTSS Tier 3 (K-3) supports at my school. A self-study is a form of research educators use to understand their practice (Austin & Senese, 2004; Loughran, Hamilton, LaBoskey, & Russell, 2004; Loughran & Northfield, 1998). In this self-study, I recount my journey as a principal, explaining in detail how I, as the leader, support teachers in the implementation of Tier 3 supports. To inform my self-study, I document and reflect on my actions using reflective journaling. The rationale for this study is driven from a desire to understand how I can provide the tools and support teachers/staff and administrators need to effectively implement MTSS, particularly at the Tier 3 level. My findings identify that as a leader I am an advocate and more aligned to Sergiovanni's Head, Hand and Heart. [The dissertation citations contained here are published with the permission of ProQuest LLC. Further reproduction is prohibited without permission. Copies of dissertations may be obtained by Telephone (800) 1-800-521-0600. Web page: http://bibliotheek.ehb.be:2222/en-US/products/dissertations/individuals.shtml.]