Levity and Learning: AI Leadership 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 experiment with new tools like AI without the fear of failure. Beyond his administrative duties, Jordan is active on Instagram (@jordangfigueiredo), where he shares reels aimed at bringing levity and joy to the role of school leadership. He is currently exploring the potential of AI assistants to streamline school operations and better align with strategic system goals.

Episode Resource Links:

-WCDSB Zero to Infinity Scale

-Tutorial Video: How to create a Gem

-Webinar: AI-Resistant Assessment: the ADAPT Framework

Want to know more?

You can check out our: WCDSB GenAI Guidelines, infographics, and Innovation website: https://innovate.wcdsb.ca/

Feedback? You can ask your questions or give us feedback on the show here 

Want to get in touch? Contact Katrina & Whitney by email at: katrina.gouett@wcdsb.ca and whitney.mckinley@wcdsb.ca or on LinkedIn

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