Cultivating communities through great leaders in education

Authored by Josh Herring, Paul Weinhold

By Josh Herring and Paul Weinhold

With the expansion of North Carolina’s Opportunity Scholarship, every family in North Carolina is now eligible to have educational dollars “follow the child” rather than automatically go to the district public school. The school choice movement has been working on this for decades, and 10 states moving to establish educational savings accounts have created massive incentives for educational innovation. This is no time for school choice advocates to rest, but rather to consider the need for new models of school leadership development.

Classical education is the largest field of new schools that benefits from expanded state funding options. These schools are experiencing an enormous boom, and are successful in part because they do not participate in mainstream educational views. For this success to continue, schools need new methods of cultivating wisdom within teachers and aspiring school leaders.

We contend that the deliberate cultivation of virtues, specifically the virtue of prudence, constitutes the best preparation for classical school leaders. 

Prudence is of paramount importance because leadership arises primarily from the character of the leader, not from the mere application of ideas or skills. As with leadership, so with schools. Schools are first and foremost local communities of persons, not merely the instantiations of broad educational theories or programs. Yet leading a school community has never been more difficult than in recent years. Never before have school leaders been so inundated with crises and politicization from outside the school community. Never have they been more continuously engaged in triaging parent, student, and faculty needs within the school community. Today’s classical school leaders must possess equanimity, poise, circumspection, and wise decision-making. Moreover, they must often exercise these qualities while mediating between and among disputing factions. In short, classical school leaders must possess an abundance of prudence if they are to navigate these turbulent times well.   

Aristotle statue located at Stageira of Greece (birthplace of the philosopher)

What is prudence? Prudence, according to Aristotle, is an intellectual virtue, the one by which we calculate how to apply a universal principle in a particular situation. Knowing that the car line should be safe, efficient, and friendly is a principle. Knowing how to keep an actual school’s car line from devolving into a Hobbesian “war of all against all” takes the exercise of prudence. The prudent leader perceives both a universal principle and all of the details of his local situation; he perceives what good can be achieved in that situation; and he takes the right actions to achieve that good. In recent years, classical educators have achieved much in the way of contemplating the true, the good, and the beautiful in the Great Books and the life of the mind. But prudence is not a virtue of contemplating the eternal and unchangeable things. It is a virtue of deliberating, choosing, and acting in the variable world that we inhabit today.

It’s understandable, then, that classical school leaders often turn to consultants, management books, and modern leadership theories as models of imitation. After all, the school leader’s day-to-day does not consist of lectures, seminars, and quiet reading but of countless decisions made with incomplete information for which there are no do-overs. Yet in the same way that Dorothy Sayers argued for a recovery of “the lost tools of learning,” classical school leaders ought to take an ad fontes approach to the development of prudence. We need to imitate the great leaders of the past, leaders who read Xenophon, Thucydides, Plutarch, Cicero, Shakespeare, and others in the tradition like a quarterback watches film. They turned to these books to form their imaginations and their characters. They wrestled with the decisions of their forebears, comparing them to one another and themselves. Classical schools need leaders who have shaped their characters in the same way. 

This mode of reading from the great tradition must be distinct from merely learning about prudence. That is not the same as becoming prudent for oneself. Kenny Rogers’ song, “The Gambler,” illustrates this tension: “You’ve got to know when to hold ‘em, and know when to fold ‘em.”  Just knowing poker strategy is not the same as knowing “when to hold ‘em” and “when to fold ‘em.” That application of principle to circumstance is prudence

Yet there are challenges to cultivating prudence in school leaders. One is that it takes time. In the normal course of events, a teacher may spend many years preparing for a leadership position in a school. The challenge is that schools need prudent leadership now, not 10 or 15 years from now. The expansion possibilities enabled by school choice bills, the perpetually waitlisted grades at successful classical charters and private classical schools, and the explosion of classical Christian schools, all point to the enormous demand from parents for this kind of education. Such schools have a limited supply of people ready to step into leadership positions, so structuring for leadership development is key to increasing school options for local communities.  

A second challenge is that experience alone is insufficient to develop prudence. Prudence is not acquired by osmosis, and years on the job do not equate to greater wisdom. You have to have the right kind of experience–and experience it in the right way–with attention to the right principles. The experienced person may have a knack for deliberating well in familiar situations, yet find it difficult to navigate new challenges. 

What is needed is intentional guidance through the Great Books, intending to understand the virtue of prudence, together with the practical application of that virtue in the domain of K-12 schools.

What are some examples of this kind of intentional cultivation of prudence for today’s classical school leaders? Below we describe two such programs that seek to cultivate prudence in school leaders.

One is the APEX Program for School Leadership. APEX is a series of short online courses that take a virtue ethics approach to leadership. The curriculum is a combination of Great Books seminars and practical application through case studies and scenario-based learning. The mode of instruction is Socratic, dialogical, and collaborative–with the intentional aim of cultivating the learner’s prudence in preparation for K-12 classical school leadership. There are pathways for aspiring deans, assistant heads, and heads of school. APEX participants encounter real school leaders who share their experiences in a personal and transformative way. In the months ahead, APEX also plans to offer a “Lives of Great Leaders” series, so that its participants can learn from the wisdom of the past in order to pivot into the future.

Thales College, Raleigh, North Carolina.

Thales College has put together another such program. The Certificate in Classical Education Philosophy (CCEP) takes working teachers and administrators through a sequence of eight courses that help provide a philosophical framework for school leadership. Designed with working professionals in mind, the CCEP assumes that participants have, or will gain, the experiential knowledge of school management through working as Heads of schools, assistant principals, or deans. What they cannot gain is the understanding of first principles that were, until recently, the province of an undergraduate liberal arts education. CCEP courses create a structure to help teachers read deeply, discuss well, and contemplate the truths at the heart of classical education. Over this two-year certificate program, participants complete eight courses:

  • Philosophical Anthropology
  • Classical Pedagogy
  • History of Education
  • Virtuous Leadership
  • Core Texts: Humanities
  • Core Experiments + Ideas
  • Classical Philosophy and Ethics
  • Writing for Leadership

Each course is built around reading specific authors; for Philosophical Anthropology, participants read C.S. Lewis’s “The Abolition of Man,” Russell Kirk’s “Enemies of the Permanent Things, and selections of Richard M. Weaver’s “Ideas Have Consequences.” Classes are structured as nine-week seminar experiences, with courses offered each quarter through a combination of Canvas LMS and Google Meet programs. The CCEP seeks to enable working educators to engage in the habits of self-formation that build awareness of the wisdom found within the great tradition.

In recent years, hundreds of new schools have been founded across the United States, many with unique models. The variety of kinds of schools means that school leadership should be formed with a stronger focus on universal principles that can be applied in particular contexts.

In the Triangle region of North Carolina, the cities of Raleigh-Durham and their surrounding suburbs, consider the following examples: Iron Academy in Raleigh focuses exclusively on boy’s education, preparing them for lives of virtuous leadership; its sister school Academy31, just launched with a middle school (and soon high school) program focusing exclusively on girl’s education. Haw River Christian Academy in Pittsboro offers a strong humanities-based Christian classical education in Pittsboro. Sola Gratia Classical Academy is a university-model school providing a unique educational experience to homeschool families: students come in-person for 2-3 days for instruction and complete assigned homework under parental supervision. Bradford Academy in Mebane offers an academically rigorous, Christian worldview-focused curriculum. Wake Preparatory Academy, a charter school in Youngsville, combines moral instruction, athletic opportunities, and a large school experience for Wake County families. Youngsville Academy is a classical charter school seeking to convey the Great Tradition to students of all backgrounds. Each school comprises a specific community, faces unique challenges and opportunities, and pursues different goals for growth. At the same time, they all serve children and seek to form students who can thrive as adults. Each of these schools increases the educational excellence of their communities. To continue growing, they need leaders who can contemplate universal wisdom and apply it to their particular contexts. This paragraph could be replicated dozens of times with new schools that have begun across the United States.

The education revolution is rolling, and for that revolution to flourish, schools must cultivate the school leaders of the next generation in the wisdom of the great tradition. Such preparation equips them to “stand on the shoulders of giants” in whichever circumstances their schools face.

Josh Herring is professor of Classical Education at Thales College in Wake Forest, North Carolina.

Dr. Paul Weinhold directs the APEX Program for School Leadership. He has served in numerous teaching and administrative roles, including headmaster at North Phoenix Preparatory Academy for four years. He currently serves as director of continuing education for Great Hearts Academies, where he leads the national network of teachers in their pursuit of personal and professional development.  Dr. Weinhold also directs the Academy for Classical Teachers, an online intellectual enrichment program designed to deepen teachers’ pursuit of Truth, Goodness, and Beauty.

Authored by:Josh Herring


Authored by:Paul Weinhold


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