Structured mentoring programs for new principals are designed to support and enhance their professional abilities. Providing mentoring support for new principals has benefits that extend beyond the novice principal to the mentor, school, and school district. Although the benefits of principal mentoring are established, mentoring of new principals is not a common practice in many school districts. The purpose of this study was to investigate the perceptions of principals and district administrators regarding the benefits and challenges of principal mentoring, as well as perceptions surrounding implementation. This qualitative phenomenological research was structured to describe views on principal mentoring and determine areas of focus for mentoring. This study examined views of principals and district administrators in a semi-rural area of Idaho, a state without mandated or funded principal mentoring. The data from the participants in this study produced three areas that should be part of a formalized mentoring process: personal (organization, time management, emotional support, managing stress, and professional ethics), instructional leadership (district-specific learning and curricular requirements, teacher support and evaluation, using data to make decisions, and staff development), and management (district financial and policy processes, student behavioral issues, difficult relationships and stakeholders, and legal compliance). The three areas are foundational for a program and need balance to help support student learning. Mentoring can ensure the necessary balance.