Hillsdale College
March 10, 2022
One Academy LN, Hillsdale, MI
Job Type


About the job

Hillsdale College seeks prospective school headmasters for its network of affiliated public charter and private schools. Headmasters are hired by each school's board, but vetted and approved by Hillsdale College's K-12 Education Office. Strong applicants will be interviewed by Hillsdale College and, if chosen, recommended to local founding boards. Learn more about Hillsdale College's work in K-12 education and see a map of our affiliated schools at k12.hillsdale.edu.


Job Description 


A classical school leader is an important figure in a school and its surrounding community. He or she is entrusted with the education and well-being of its students and the academic reputation of that community, acting as a steward of substantial public or private funds and, ultimately, a contributor to the future of the nation through the passing on of wisdom and virtue to its future citizens.


The leader of a classical school knows that he or she is shaping young men and women for lives of virtue, and that a classical education is a training for both the mind and the heart. The leader is equally attentive to the school's curriculum, pedagogy, and culture, because he or she knows that ethical and intellectual living is practiced in and outside of the classroom. The school leader is an example of virtuous living and the love of learning for its own sake to the students and his or her community. He or she understands the value of a liberal arts education, and can articulate that clearly and effectively. As a proponent of American classical education informed by the Western tradition, the school leader builds a culture focused on principled self-government and civic responsibility.


Qualities and Characteristics

  • Leadership. Specifically, the ability to discern the ends that fulfill the nature and purpose of the organization, and to chart a course to reach those ends; the ability to inform and inspire people to follow, to commit, to take responsibility, to perform, and to cooperate in an effective manner. The ability to raise up leaders in an organization.
  • Intellectual depth and serious understanding of the life of the mind befitting of the leader of an academic institution with a love of learning demonstrated by the ongoing personal pursuit of knowledge and the desire to share that knowledge with others.
  • A commitment to school reform, energized with courage and governed by prudence.
  • A generator of trust and confidence from others within his or her leadership by exhibiting unwavering personal integrity, honesty, and decisiveness.
  • A person of excellent moral character.


Knowledge and Skills

  • A broad understanding of the classical liberal arts, its roots in the Western tradition, and its historical presence in American education prior to the 20th century.
  • An understanding of the ills that plague contemporary primary and secondary schools and the root causes of those problems.
  • Knowledge of the craft of the educator, and the ability to teach well.
  • The ability to coach teachers to greater degrees of effectiveness in the classroom.
  • The ability to communicate effectively in both oral and written forms.
  • The ability to maintain a high degree of energy and personal productivity, and to effectively manage the yield of others. The ability to prioritize and get things done.
  • A general understanding of personnel management principles, including recruiting and hiring, supervising and evaluating, and individual and organizational development.
  • The intellectual and emotional strength to have difficult conversations.
  • A general understanding of financial management principles, including planning a budget and managing to it throughout a school year, the needs and expectation of regular auditing, and a system of sound fiscal controls.
  • An understanding of the school’s state accountability or accreditation system for public or private schools, as appropriate, and laws relevant to same.

Duties and Responsibilities

  • Provides general management of all school operations, including academic, financial, personnel, regulatory, and facility areas.
  • Observes teachers at defined intervals, documents results, and provides feedback as mentor and supervisor.
  • Reports at regular school board meetings on the status of operations and plans for upcoming activities.
  • Represents the school as the senior executive leader in interactions with the public, the school constituencies, the authorizer or accreditor, and other government agencies.


Other Expected Characteristics of a Classical School Leader

  • The school leader is well-organized and takes responsibility for everything that occurs within the school, carrying out his or her charge with humility and flexibility with a willingness to take on any task even if it seems menial. He or she is keen on delegation with clear direction, yet accountable for every facet of the school.
  • The school leader is pleasant, engaging, personable, and empathetic—important traits as he or she interacts with parents, community members, teachers, students, and others. The school leader knows how to build trust through excellent communication, which oftentimes means only listening, and by being consistent with expectations and follow-through. The school leader is firm and kind, prudent and just.
  • The school leader can build an administrative team. He or she knows the mission and knows how to hire well to support that mission. A school leader knows his or her own strengths and weaknesses, and will hire assistant principals and deans who will offset those weaknesses.
  • The school leader is rooted in the classical tradition and has an appreciation for the art of teaching, with a clear vision for his or her own classroom, having experienced it firsthand.
  • The school leader understands and communicates with the broader classical movement to promote better education in our country and is committed to the larger network of schools of which he or she may be a part.
  • The school leader regularly coaches each teacher on classroom management, instruction, and culture.
  • The school leader has a clarity of focus, and yet is open to ideas and implements the best of them from his or her community, not just from personal preferences.
  • The school leader is public-spirited, ambitious about the school and its effect on the wider community, state, and nation. He or she is committed to the local community as an active participant, an energetic advocate for classical education as being good for all learners.
  • The school leader likes interacting with children and believes that classical education leads them on the path to true happiness.
  • The school leader has a recognizable executive aptitude for the business and operational aspects of school leadership. He or she is able to put first things first and has the capacity to multi-task.


Applicants should email K12@hillsdale.edu a resume, cover letter, and a brief statement on classical education (1-2 pages).


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