In this episode, we sit down with Michael Deperro, Michael Deperro, Senior Coordinator of Faculty Development & Professionalism at Case Western Reserve University, to uncover how AI is shaking up higher education. Michael pulls back the curtain on how his team is using AI to clear away the “digital laundry” of repetitive back-office work, build a retrieval-augmented generation hub that simplifies faculty processes, and make room for staff to focus on what really matters: people.
Join us as we discuss:
- [5:45] Why legacy systems are one of the biggest hurdles to AI integration
- [10:33] “Boring AI” use cases that really work
- [16:38] Trust, transparency, and responsibility in AI adoption
Check out these resources we mentioned during the podcast:
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Episode Prompt:
Episode prompt:
Initial Setup Prompt:
I need to work through a strategic decision/challenge and want to use you as a thought partner. Here's my situation:
**Challenge/Decision:** [DESCRIBE YOUR SPECIFIC SITUATION OR DECISION]
**My Current Thinking:** [OUTLINE YOUR PROPOSED SOLUTION OR APPROACH]
**Context:**
- My role: [YOUR POSITION]
- Institution type: [E.G., PUBLIC UNIVERSITY, PRIVATE COLLEGE]
- Stakeholders involved: [LIST KEY GROUPS AFFECTED]
- Timeline: [WHEN DECISION NEEDS TO BE MADE]
- Resources available: [BUDGET, STAFF, TIME CONSTRAINTS]
I want you to act as a critical thought partner. Your job is to:
1. Challenge my assumptions and reasoning
2. Identify potential blind spots or risks I haven't considered
3. Suggest alternative approaches or solutions
4. Help me stress-test this idea before presenting it to stakeholders
Please be direct in your feedback - I need honest analysis, not validation.
Round 1: Devil's Advocate Analysis
Now I want you to play devil's advocate with my proposal. Assume you're a skeptical colleague who needs to be convinced this is a good idea.
Push back on my reasoning by addressing:
- What are the weakest points in my logic?
- What could go wrong with this approach?
- What am I not considering about implementation challenges?
- How might different stakeholders react negatively?
- What are the opportunity costs of pursuing this direction?
- Where might I be overestimating benefits or underestimating costs?
Be specific about potential problems and explain your reasoning.
Round 2: Alternative Solutions
Based on our discussion, now help me brainstorm alternative approaches to this challenge.
Consider:
- What would a completely different solution look like?
- How would someone with [SPECIFIC EXPERTISE - e.g., finance background, student affairs experience, technology focus] approach this differently?
- What if we had unlimited resources? What if we had severely limited resources?
- What are 2-3 entirely different ways to solve the underlying problem?
- What would the "do nothing" option look like and what are its implications?
Present these alternatives with brief pros/cons for each.
Round 3: Implementation Reality Check
Let's get practical about implementation. Assume my organization decides to move forward with [CHOSEN APPROACH].
Help me identify:
- What are the first 3 concrete steps we'd need to take?
- What resistance should I expect and from whom?
- What metrics should we use to measure success?
- What would "failure" look like and how would we know?
- What contingency plans should we have ready?
- How long should we expect this to take realistically?
- What skills or resources do we need that we might not have?
Be specific about potential roadblocks and mitigation strategies.
Cross-Model Analysis Prompt (for use with different AI models):
I've been working through a strategic decision with another AI model. Here's what I proposed and the feedback I received:
**My Original Proposal:** [RESTATE YOUR IDEA]
**Previous AI's Analysis:** [PASTE KEY FEEDBACK FROM OTHER MODEL]
Now I want your perspective:
1. Do you agree or disagree with the previous analysis? Why?
2. What did the other model miss or get wrong?
3. What additional considerations should I factor in?
4. How would you refine or modify the previous recommendations?
Feel free to challenge the other model's reasoning if you see flaws in its logic.
Final Synthesis Prompt:
I've now worked through this decision with multiple AI models and perspectives. Help me synthesize everything into a final recommendation.
Based on all our discussions, provide:
**Recommended Action:** What should I do and why?
**Key Success Factors:** What are the 3 most critical elements for success?
**Primary Risks:** What are the 2-3 biggest threats to watch for?
**Communication Strategy:** How should I present this to stakeholders?
**Decision Timeline:** What's the optimal sequence and timing for implementation?
**Metrics for Success:** How will we know if this is working?
Keep your final recommendation concise but actionable.
Guest Name: Michael Deperro, Senior Coordinator, Faculty Development and Professionalism
Guest Social: https://www.linkedin.com/in/michael-deperro/
Guest Bio: Michael DePerro designs and leads leadership development programs for faculty at Case Western Reserve University School of Medicine, where he's passionate about helping individuals and institutions think creatively, embrace change, and pursue bold ideas through innovation and entrepreneurial thinking. His approach combines practical leadership development with forward-thinking strategies that prepare academic leaders for an evolving landscape.
Michael launched the first AI Council for Administration at Ohio University's College of Business and co-founded AI Woodstock Cleveland, a grassroots initiative bringing together technologists, business leaders, and problem solvers to explore AI's potential. He now helps higher education leaders build AI literacy, focusing on responsible and ethical implementation that enhances human expertise. His work spans healthcare education, business administration, and institutional leadership, always with an eye toward practical applications that solve real problems and elevate the unique skills educators bring to their work.
