School Leadership: The Unsung Catalyst for Student Success and Well-being in 2026

In the ongoing conversation about improving education, much attention is often placed on curriculum, technology, and funding. However, a recent interview published by Education Next with Greg Richmond, a seasoned education administrator with experience across district, charter, and private school sectors, underscores a critical, often understated, factor: school leadership. Richmond, who recently stepped down as superintendent of schools for the Archdiocese of Chicago, shared insights gleaned from decades of experience, suggesting that effective leadership is the single most important element in a school's success.

His reflections offer a valuable lens through which to view the challenges and opportunities facing schools today, providing practical takeaways for parents, teachers, and school administrators alike. Understanding the nuances of school leadership can help stakeholders advocate for environments that genuinely support learning and well-being.

The School as the Unit of Change: Beyond the Classroom

Richmond's core belief, according to Education Next, is that the school itself, rather than individual classrooms or entire systems, is the fundamental unit of change in education reform. He posits that school culture acts as a critical driver of improvement. While an individual teacher might excel, their impact is limited if the broader school culture doesn't universally expect ambitious instruction or foster collaboration among staff. "It is the adults inside who determine that school’s expectations and norms," Richmond stated, highlighting that adults also dictate whether students feel known and supported, and whether quality instruction is consistently delivered.

This perspective suggests that focusing solely on teacher training or classroom resources, while important, may miss the larger picture. A robust school culture, nurtured by strong leadership, creates an environment where every educator can thrive and every student can benefit. For parents, this means looking beyond individual teacher evaluations to understand the overall ethos and support systems within a school. For teachers, it emphasizes the importance of collective responsibility and a shared vision for student growth. Students, in turn, benefit from a consistent, supportive, and high-expectation environment that permeates every aspect of their school day.

Leadership: The Foremost Driver, Not Just a Facilitator

When discussing various factors like governance, autonomy, accountability, and market pressure, Richmond firmly asserts that "leadership is what matters most in a school." He explains that a strong school leader can unite the school community around a shared vision of excellence, ambitious instruction, collaborative teaching, and behavioral norms that foster growth. These external forces, such as governance or regulation, can either help or hinder a leader, acting as a "headwind or a tailwind." However, Richmond emphasizes that even favorable external conditions cannot produce an excellent school without a strong leader at the helm. Conversely, a strong leader can often overcome significant challenges posed by unfavorable external factors.

This insight is particularly relevant in 2026, as schools navigate evolving educational landscapes and continue to adapt to new technologies. For students seeking additional academic support, platforms like COSMIQ offer free voice-driven AI tutoring, providing personalized assistance that can complement a strong school environment. A good school leader understands how to integrate such resources effectively to empower both students and teachers, further strengthening the school's overall educational offering.

Navigating Sector Differences: Resources vs. Flexibility

Richmond's experience across district, charter, and private schools provides a unique comparative analysis. He notes that district schools often have the advantage of greater funding, though this frequently comes with "over-politicization and over-regulation." Charter schools, he observes, typically have slightly less funding but also less politics and regulation, creating "better conditions for teaching and learning, but fewer resources." Private schools vary widely, with some elite institutions having substantial resources and others operating on much tighter budgets, but generally benefit from less politics and regulation.

Intriguingly, Richmond personally preferred the environment with "less money, less politics, and less regulation because it’s what best empowered our educators." He provided a vivid example from the pandemic, where Catholic schools in Chicago remained open for in-person instruction during the 2020-21 and 2021-22 school years, unlike public schools in the same city. This, he attributes, to the Catholic schools' greater flexibility in setting calendars and schedules, and their ability to recruit talent from diverse professional backgrounds, including those who transitioned into teaching from other sectors.

This flexibility, while not always tied to greater funding, can be a powerful tool for leaders to tailor educational experiences to their specific communities. For parents considering different school options, understanding these trade-offs between resources and autonomy can be crucial. It highlights that the "best" school isn't solely defined by its budget but by its ability to adapt and serve its students effectively.

Protecting Principals: The Instructional Leader's Role

One significant shift in Richmond's perspective came when he moved from overseeing to actually running schools. He became more attuned to the administrative and compliance demands placed on principals. He argues that excessive administrative burdens diminish a principal's time and capacity to be an instructional leader. When principals cannot fulfill this role, teachers may become isolated, leading to an erosion of alignment, rigor, and overall school culture.

Richmond shared an example where he deliberately protected principals from a central administration demand for teachers to watch numerous, universally disliked online videos about the Catechism. By successfully advocating for the removal of this burdensome requirement, he allowed principals and teachers to focus on more effective, less time-consuming activities. This illustrates a critical aspect of effective leadership: balancing institutional demands with the needs of those on the front lines of education. For teachers, having a principal who acts as an instructional leader and shields them from unnecessary bureaucracy can be transformative, fostering a more collaborative and focused teaching environment. Students ultimately benefit from a school where leaders prioritize pedagogical support over compliance for compliance's sake.

Connecting and Learning Across Sectors

Despite the distinct characteristics of each sector, Richmond expresses concern about the lack of convergence and connection between them. He describes feeling like he had entered a "parallel dimension" when transitioning to Catholic education due to the unfamiliar organizations and issues. This disconnection, he believes, is a "real loss for everybody, because there are positive things happening in all three sectors that the others could learn from."

He cited higher levels of parent engagement and cost-consciousness in Catholic schools as examples that district and charter schools could learn from. Conversely, he noted that many charter schools excel in having a clearly defined vision and mission, which lifts the performance of the entire school community. District schools, he applauded for their greater willingness and ability to serve all students, particularly those in special education and English Language Learners – an area where some Catholic schools, he admitted, could improve. This exchange of best practices is vital for the continuous improvement of the entire educational landscape. Tools like COSMIQ for schools can help bridge some of these gaps by providing accessible learning support regardless of a school's sector or resources.

Conclusion

Greg Richmond's reflections provide a powerful reminder that while resources and policies are important, the human element of leadership is paramount in shaping a school's success. Strong leaders cultivate positive school cultures, empower educators, and navigate complex environments to create optimal learning conditions for students. As schools continue to evolve, recognizing and investing in effective leadership at all levels will be crucial for fostering environments where every student can thrive academically and emotionally.