Levity and Learning: AI Leadership at St. Benedict CSS

Levity and Learning: AI Leadership at St. Benedict CSS

From Deep Learning Dialogues by Katrina Gouett and Whitney McKinley

March 27, 2026 · 34 min · Season 3 · Episode 23

About this episode

Jordan Figueiredo discusses AI leadership and fostering a culture of curiosity at St. Benedict CSS.

In this episode of Deep Learning Dialogues , hosts Whitney McKinley and Katrina Gouett are joined by Jordan Figueiredo the principal of St. Benedict Catholic Secondary School . Jordan shares his leadership stance on artificial intelligence, moving beyond simple "guardrails" to foster a culture of curiosity and vulnerability among his staff. The conversation explores how to manage the "ping-pong" effect of innovation and how to establish the psychological safety necessary for educators to move from "shadow use" of AI to shared, open practice. From leveraging "lead learners" in staff meetings to using AI "Gems" for analyzing student achievement data, Jordan illustrates how a human-centered approach to technology can actually amplify relationships and professional practice in a large secondary school. Jordan Figueiredo is the Principal of St. Benedict Catholic Secondary School in Cambridge Ontario. Known for his commitment to building a culture of openness and innovation, Jordan focuses on supporting both student and adult learning through collaborative leadership and professional trust. He is an advocate for "being vulnerable on purpose and out loud," encouraging his staff to…

People in this episode

Hosts: Katrina Gouett, Whitney McKinley

Guest: Jordan Figueiredo

Topics covered

  • AI leadership
  • education
  • psychological safety
  • innovation
  • collaborative leadership

Keywords

  • artificial intelligence
  • leadership
  • education
  • psychological safety
  • collaborative learning

Mentioned in this episode

Organizations: St. Benedict Catholic Secondary School

Places: Cambridge Ontario

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