Podcast Summary

Hillsdale College K-12 Classical Education Podcast

Episode: Apprenticing Excellence: Inside Hillsdale's School Leader Fellowship Program
Date: January 19, 2026
Host: Scott Bertram
Guest: Benjamin Payne, Director of Leader Support, Hillsdale College K-12 Education Office
Length: ~25 minutes

Main Theme

This episode gives listeners a thorough look inside Hillsdale College's K-12 School Leader Fellows Program—a unique, paid yearlong fellowship designed to cultivate exceptional school leaders rooted in the classical education tradition. Benjamin Payne explicates the program's structure, its hands-on apprenticeship model, professional development curriculum, and the transformative impact it has on participating fellows and the broader classical education movement.

Key Discussion Points and Insights

1. Program Overview and Mission (01:05–02:50)

• The School Leader Fellows Program is a one-year, paid apprenticeship aimed at preparing future heads of classical schools. The two primary components:

  • On-site Apprenticeship: Fellows spend a year at a member school, shadowing and assisting experienced school leaders without the pressure of final decision-making responsibilities.
  • Professional Development: Monthly virtual sessions along with in-person conferences at Hillsdale, fostering both philosophical and practical leadership skills.

• Alignment with Hillsdale’s founding mission from 1844: “Preserve liberty through sound learning.”

  "We need to bring in and train up the best leaders possible to lead our schools and to lead this effort."
  —Benjamin Payne (01:45)

2. Distinctiveness of the Fellowship (03:06–04:49)

• Unlike many online, asynchronous leadership programs, this fellowship uniquely blends real-world, in-person experience with live, interactive professional development.

• Fellows participate in:

  • Parent meetings
  • Planning sessions (scheduling, HR, budgeting)
  • Shadowing roles such as assistant principal or dean
  • Implementing projects and observing the nuances of school leadership

  "You get a full year, basically without responsibility, to shadow really strong school leaders on the ground and learn what it's like...”
  —Benjamin Payne (03:37)

• The fellowship also builds a cohort community, fostering peer learning and support.

3. Ideal Candidate Backgrounds (04:49–06:23)

• The program seeks candidates who are smart, humble, industrious, and committed to forming self-governing citizens.

• Successful fellows come from varied backgrounds:

  • Veteran teachers moving into administration
  • Corporate executives seeking purpose in education
  • Military veterans
  • Homeschooling parents called to institutional leadership

  "You have to love children and believe in education as one of the primary ways that we're going to restore this American experiment to what it should be."
  —Benjamin Payne (05:58)

4. Apprenticeship Experience in Detail (06:23–08:55)

• Structure: July 1–June 30; fellows join school preparation before the academic year, participate in daily administrative life, attend board meetings, interact with parents, and assist in various projects.

• Opportunity to observe, reflect, and develop a personal vision for effective school leadership without the weight of final responsibility.

  "It really equips that person to reflect on how they would handle all of these challenging situations that school leaders face."
  —Benjamin Payne (08:22)

5. Intellectual and Professional Development (08:55–11:13)

• Readings span the classical canon (e.g., Plato’s Republic, Hicks’ Norms and Nobility) and modern leadership texts (Teach Like a Champion, Lencioni, The Culture Code).

• Monthly group discussion deepens understanding.

• Focus on blending philosophical grounding in “the true, the good, and the beautiful” with pragmatic leadership and management skills.

  "It's important to remain rooted in those texts and that thought... At the same time, you...have to be equipped with the skills and leadership practices to do that well."
  —Benjamin Payne (10:18)

6. Real-World Skill Development and Resources (11:13–13:03)

• Fellows gain hands-on skills in:

  • Financial management
  • Fundraising
  • Teacher coaching
  • Board governance

• Access to Hillsdale's K-12 online library (3,000+ resources), teacher support team, and exclusive professional mentorship.

  "I don't know another opportunity quite like this for an aspiring leader."
  —Benjamin Payne (12:17)

7. Capstone Project (13:03–15:53)

• Each fellow completes a capstone project, presented at the annual summer conference.

• Projects address practical or philosophical challenges in classical education, e.g.:

  • A resource for engaging parents throughout the school year
  • New approaches for supporting struggling students through classical frameworks

  "The purpose...is to allow each Leader Fellow an opportunity to dive a little deeper into a topic that they feel passionate about...that will benefit our entire movement."
  —Benjamin Payne (13:46)

8. Ongoing Feedback and Self-Development (15:53–18:09)

• Monthly mentorship sessions and journal reflections, reviewed by the K-12 office.

• Fellows use OptimalWork and the Self Authoring Suite to clarify and pursue long-term aspirations, guided by classical philosophical principles and research from Jordan Peterson and others.

  "...it gives each fellow a framework to intentionally articulate a vision for themselves as individuals and as leaders."
  —Benjamin Payne (16:23)

9. Success Stories and Placement Outcomes (18:09–19:49)

• Graduates have:

  • Become principals at member schools
  • Moved directly into founding new classical schools as head of school
  • Taken on assistant principal and director roles

  "Our past Leader Fellows flourish...ready to lead this engine moving forward."
  —Benjamin Payne (18:25)

10. Diversity of Placement Sites (19:49–22:25)

• Fellowship sites include award-winning and geographically diverse schools (e.g., Michigan, Ohio, California, Idaho, Georgia, Wisconsin).
• Sites chosen for strong leadership and high performance (Salvatore Prize winners/runners-up).
• Some placements offer direct paths to founding head-of-school positions.

11. Program Benefits and Community (22:25–25:26)

• Full salary during the fellowship—rare among leadership programs

• Participation in multiple national conferences and school visits

• Extensive networking and sustained peer relationships

  "Our Leader Fellows are forming bonds and friendships with other really strong leaders that will last the rest of their careers and lives."
  —Benjamin Payne (24:41)

12. Application Advice (25:26–26:26)

• Prospective applicants are encouraged to research classical education, especially the Hillsdale model, and visit local schools for on-the-ground experience.

  "Dive into that...see what that excellence looks like on the ground. And then whenever you're ready, just reach out, go to our website and apply."
  —Benjamin Payne (26:02)

Notable Quotes and Memorable Moments

• On true leadership preparation:

  "It's not enough to just be a good person or to just, just want to do it well, but you actually have to be equipped with...leadership practices to do that well." (10:09)

• On the fellowship experience:

  "You get a year of learning for an entire year while still having that access to all that leadership has to go through." (07:33)

• On the cohort dynamic:

  "You go through this experience together, and our Leader Fellows are forming bonds and friendships…that will last the rest of their careers and lives." (24:41)

Timestamps for Important Segments

• Program Overview & Mission: 01:05–02:50
• What Makes It Unique: 03:06–04:49
• Ideal Candidates: 04:49–06:23
• Detailed Apprenticeship Experience: 06:23–08:55
• Intellectual/Professional Learning: 08:55–11:13
• Skill Development & Resources: 11:13–13:03
• Capstone Projects: 13:03–15:53
• Feedback & Self-Development: 15:53–18:09
• Graduate Outcomes: 18:09–19:49
• Placement Site Diversity: 19:49–22:25
• Program Benefits: 22:25–25:26
• Application Advice: 25:26–26:26

Tone and Language

Throughout the episode, both host and guest maintain an inviting, earnest, and mission-driven tone. Benjamin Payne is passionate about nurturing future leaders and transparent about the program’s strengths. The conversation is practical yet aspirational, reflecting the blend of philosophical roots and real-world application that define classical education and the fellowship.

For Further Information

• Learn more or apply: k12.hillsdale.edu
• Direct link to School Leader Fellows Program in episode description