In this qualitative ethnographic research study, I focused on a first-year assistant principal's leadership experiences in an urban PK-8 school environment and the coaching, mentoring, support, and training needed to develop an effective building administrator who will be retained in the assistant principal position. The guiding research questions included the following: (a) What are an assistant principal's leadership experiences in an urban PK-8 school environment? (b) Based on an assistant principal's leadership experiences in an urban PK-8 school, what systems and structures might build their leadership capacity and outlook on educational leadership? and (c) Based on an assistant principal's leadership experiences in an urban PK-8 school, what coaching, mentoring, support, and training might improve their leadership capacity and outlook on educational leadership? The assistant principal position serves as the gateway to a leadership position; however, many assistant principals do not receive the mentorship, training, and coaching they need to succeed. Educational leadership programs have not completely prepared candidates to enter new assistant principal positions. The training at the postsecondary level helps to prepare candidates to enter leadership roles, but they lack specificity for the assistant principal position. This study's aim was to explain the experiences of an assistant principal in a first-person narrative form and to help new assistant principals understand their roles as well as provide guidance to inform practice. The three major themes that emerged from the findings of this research study involved: (a) clash of values and expectations; (b) health, safety, and well-being; and (c) personal growth. The researcher learned that being authentic in leadership includes recognizing personal strengths and weaknesses. Situations in which leaders do not professionally reflect on their leadership practices can lead to chaotic, dysfunctional, traumatic, and unhealthy experiences. An assistant principal's health, safety, and well-being should be fostered, and this requires time designated for instructional leadership along with opportunities to build trust and relationships. An individual's ability to serve others is fully compromised when their core values are compromised. Based on this study's findings, new assistant principals need clear communication protocols, expectations, and responsibilities, along with defined systems and structures. A key recommendation from this study, regardless of geographic location, is to provide new assistant principals with a comprehensive multiyear mentoring program to foster a successful transition into the new position. [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.]