An instructional leadership program (ILP) has offered education and support to three cohorts of educational leaders in Nova Scotia, Canada, amounting to approximately 130 participants. Quantitative and qualitative feedback from a convenience sample (n = 90) suggests that the ILP offers an extremely useful practical program; in fact, 95 percent of the sample indicates advances in the categories of professional growth, improved instructional leadership, and tangible progress in administrative effectiveness. Systemic and school environment trends have dictated that educational leaders need a skill set that positions them to respond more aptly to issues of poverty, socioemotional health, and mental health while attending to improved community building both within the school and in the greater public. This study uses surveys, interviews, and focus groups to identify emerging and impending challenges