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Abstract visualization of digital twin GPT leadership assistants
Session 23

Twin Ambitions: Scaling Our Leadership Through Custom GPTs

Thursday, June 11, 2026 1:30 PM – 2:30 PM Pitzer · Fletcher 104

About This Session

What happens when a CIO stops using AI as a search engine and starts using it as a "grounded partner"? This interactive workshop, led by Michael Cato (Bowdoin) and Barron Koralesky (Williams), explores the creation and evolution of specialized "Digital Twin" GPTs — AI assistants built using Carnegie Mellon's FRED framework (Focus, Role, Evidence, Delivery) that act as vigilant mirrors for a leader's unique style.

The session moves well past the technical "how-to" to explore the practical and philosophical lessons from building these twins — and what it means to feed an AI your leadership philosophy, historical successes, and hard-won skills so that it understands your unique institutional context.

The FRED Framework

Focus

Defining the specific purpose and scope of the Digital Twin — what decisions it helps with, what it stays out of, and how it knows the difference.

Role

Defining an AI voice that mirrors your best days — wise, empathetic, and strategically precise — rather than a generic assistant divorced from institutional context.

Evidence

The ethics and utility of feeding your AI your leadership philosophy, historical successes, CliftonStrengths data, and TKI conflict modes — so it understands you, not just prompts.

Delivery

Programming the twin to recognize personal shadows — and teaching it to challenge natural tendencies (like a Healer's conflict avoidance) when they risk institutional progress.

Learning Outcomes

  • Apply the FRED framework to create a specialized leadership GPT tailored to a liberal arts context.
  • Identify specific evidence types — strengths assessments, philosophy statements, historical decisions — that move AI from a generic tool to a genuine thinking partner.
  • Develop a roadmap for guiding other team members through creating their own Digital Twins to manage burnout and improve reflective practice.