The LearnIt Podcast with Dhiraj Hariramani

In this episode, we sit down with Curtis Ennis, Director of Education and CEO of the Halton District School Board.

Born in Jamaica and raised by a mother who never went to school herself, Curtis spent years in banking before walking away from a promotion to become a teacher. Today, as Director, he leads one of Ontario's largest school systems through what he calls adaptive challenges—the problems that have no playbook.

In this conversation, Curtis shares:

• His mother's quiet conviction: how she sewed together a school uniform so he could keep going to class, and why that memory still drives his work in education.
• The volunteer day that changed everything: the moment at a school, while he was still a bank manager, when he felt something he had never felt at the bank.
• The hardest year of his life: working full days at York University and bank back-office shifts past midnight, with two young kids at home.
• Why he leads people first: how investing in a principal nobody else wanted to work with taught him that people respond to how they are valued.
• Confident humility: the leadership idea he has come to embrace, the belief that confidence and humility are not in tension.
• The student who taught him to protect his peace: a phrase from a session on mental health that he now uses for himself.

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