The current study sought to identify and gain a deep understanding of the elements of mentoring support that experienced principals perceive to be most effective in developing beginning principals’ leadership capacity. Q-methodology was utilized to investigate the subjective opinions of public school principals within one school district in North Carolina. The research design of Q-methodology allowed the researcher to capture experienced principals’ beliefs and viewpoints about elements of mentoring support through the collection of both quantitative and qualitative data. Data analysis indicated four statistically significant factors that were named in the study: (1) Trust is the Prerequisite, (2) A Safe Place to Learn, (3) Instructional Leadership in an Era of Accountability, and (4) Relationship is Key. In addition to the statistical analysis, post-sort interviews were conducted for each emergent factor in order to gain further insight about the principals’ perceptions of mentoring support. The findings pointed to gate-keeping mechanisms that lead to better practices for mentoring support. While the content of instructional leadership rose to the top as one of the focus areas for mentoring support, findings notably highlighted the elements of trust and relationship as critical to achieving growth in leadership capacity. The current study’s findings generated implications for policy, further research, and educational practice, which are herein discussed