Hillsdale College K-12 Classical Education Podcast

Episode: Portrait of a Graduate
Date: April 28, 2025
Host: Scott Bertram
Guest: Dr. Steven Shipp, Headmaster at Seven Oaks Classical School

Overview

This episode explores the concept of a "Portrait of a Graduate," a document designed to articulate the aspirations, values, and long-term educational goals of Seven Oaks Classical School. Dr. Steven Shipp explains the genesis, purpose, and application of this portrait, sharing its role in classical education and why such clarity of vision is crucial for schools, students, and communities engaged in this educational tradition.

Key Discussion Points & Insights

1. Defining the Portrait of a Graduate

• Purpose: Provides a concise, aspirational vision for what kind of person a school seeks to graduate—serving as both an anchor and "North Star."
• Format: Typically one to two pages, with headers, brief narratives, and/or bullet points illustrating the desired attributes in graduates.
• Speaker Quote:
  • “It’s the sort of document that has the opportunity to really showcase ways in which your school might be distinct.”
    — Dr. Shipp [02:28]

2. Mission Statement vs. Portrait of a Graduate

• Mission Statement: The foundational "bedrock," focusing on what the school aims to do during a student's tenure.
• Portrait of Graduate: Extends beyond the mission, focusing on the hoped-for long-term impact in students’ lives after graduation.
• Connection: At Seven Oaks, the portrait is visually and thematically anchored by the mission statement—fostering coherence.
• Speaker Quote:
  • “The mission... is a kind of bedrock. It is a starting point of an organization... The portrait kind of extends the field of vision.”
    — Dr. Shipp [03:17]

3. Intended Audience

• All Stakeholders: Internal (faculty, staff, students) and external (parents, community, prospective families).
• Utility: Communicates vision and expectations clearly; functions as a living document for ongoing reflection and guidance.
• Speaker Quote:
  • “It is again a kind of anchor…a succinct summary of what we’re trying to accomplish.”
    — Dr. Shipp [05:11]

4. Origin and Motivation

• Growth-driven Need: As Seven Oaks expanded into a full K-12 institution, Dr. Shipp recognized the need to articulate the lasting mark they hoped to leave on students.
• Foundational Perspective: While the school is present for a significant period (up to 13 years), its influence is only the beginning of a student’s broader journey.
• Speaker Quote:
  • “It feels like a time that's ripe for trying to give articulation to what it is... what kind of lasting mark we hope the education will leave.”
    — Dr. Shipp [06:54]

5. Crafting the Portrait: Process & Choices

• Aspirational vs. Actual: Chose to describe the ideal graduate rather than the statistical average, serving as a “guiding light.”
• Category Selection: Settled on three classical virtues—moral, intellectual, and civic—as core organizing themes, closely reflecting the school mission.
• Pitfalls to Avoid:
  • Over-quantification (“paint-by-numbers” approach reduces richness)
  • Narrow definitions of success (e.g., only “college prep” or “future leaders”)
• Speaker Quote:
  • “You want to find ways to paint a portrait that… is painting a picture of a kind of ideal, but in another way is actually potentially attainable by virtually anyone.”
    — Dr. Shipp [14:40]

6. Staying True Amidst Growth

• Continuity of Leadership: Leadership consistency aids in keeping the original vision alive.
• Faculty Alignment: Intentional hiring practices ensure teachers are aligned with mission.
• Cultural Practices: Recurrent recitations and integration into code of ethics and teacher evaluations ensure continual presence.
• Speaker Quote:
  • “There have to be keepers of the vision.”
    — Dr. Shipp [10:43]

7. Making It Unique (or Not)

• Universality of Good Schools: Most classical schools will have overlapping ambitions and language, which is desirable.
• Individual Flavor: Minor differences may arise in chosen themes and points, but strong similarity signals alignment with classical ideals.
• Speaker Quote:
  • “Good schools should be attempting to do essentially the same thing. And so I would hope that there are many schools that could paint a portrait very similar to the one that we paint.”
    — Dr. Shipp [15:43]

8. Practical Applications and Benefits

• Award Selection: The portrait gives substance to distinctions such as the “Founder’s Award” for students most embodying the school’s mission.
• Teacher Evaluation: Assists administrators in evaluating faculty’s effectiveness in advancing the mission via student formation.
• Organizational Focus: Serves as a tool for recurring reflection on the first principles and core purposes of education at the school.
• Speaker Quote:
  • “It’s a gift that just keeps on giving… it helps clarify some thoughts so that as I coach teachers or as we approach the end of year teacher evaluations…”
    — Dr. Shipp [16:49]

Notable Quotes & Memorable Moments

• “We do have students for a lot of time. It’s a remarkable thing that we have approximately 180 days with students for up to 13 years.”
  — Dr. Shipp [06:41]
• “You want to talk about character, I think, as well.”
  — Dr. Shipp [13:08]
• “Most classical schools are going to be painting with the same set of colors… with a similar palette.”
  — Dr. Shipp [15:57]
• “Going through the process of writing a portrait and having a document like this… just helps focus the mind and draw us back to basic questions about what school is for, what high school is for, how to gauge if we’re doing well.”
  — Dr. Shipp [17:47]

Important Segment Timestamps

• Definition & Purpose of Portrait: [01:57]–[03:03]
• Mission vs. Portrait Discussion: [03:03]–[04:39]
• Intended Audience: [04:39]–[05:55]
• Backstory & School Growth: [06:06]–[07:45]
• Crafting Approach (Aspirational Ideal): [07:52]–[10:16]
• Challenges of Growing School & Staying True: [10:16]–[12:22]
• Mistakes & Pitfalls in Crafting: [12:22]–[15:08]
• Universality vs. Uniqueness: [15:08]–[16:39]
• Practical Application & Benefits: [16:39]–[18:28]

Final Thoughts

Dr. Steven Shipp emphasizes the importance of creating a Portrait of a Graduate as a clarifying, unifying, and practical document at the core of the classical education movement. Rather than simply parading idealistic slogans, it serves as a thoroughly considered standard—aspirational yet accessible—by which schools, teachers, students, and families can measure purpose and progress.