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In the Moment: What Working in Prison Taught Jeff Jacobs About Trust and Empathy

In this episode of What’s Possible: In the Moment, Ilene Schaffer sits down with Jeff Jacobs to explore the powerful leadership lessons he learned while working in maximum-security prisons.

Jeff talks about how his time with incarcerated individuals challenged his assumptions, deepened his empathy, and taught him the importance of psychological safety, trust, and genuine human connection. He learned the value of showing up with curiosity, asking thoughtful questions, and respecting the lived experiences of others.

This short conversation offers a deeply human reminder that trust begins when…

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