Former Superintendent Anthony Cordeiro on Relationships, Resilience, and Creativity in Education

From sweeping parking lots as a teenager to leading as a superintendent, Anthony Cordeiro reflects on his decades-long journey in education, the power of relationships, and why embracing vulnerability is essential for lasting impact.

When Anthony Cordeiro talks about education, he doesn’t begin with boardrooms or policy documents. He begins with a broom. At just 12 years old, he was hired to sweep the Halton Catholic District School Board’s parking lot every Saturday. The then Director of Education would personally hand him five dollars, sometimes twenty, along with words of encouragement. “Why don’t you think about education?” the director suggested one day. That conversation planted a seed that would grow into a 30-year career at HCDSB, culminating in his role as Superintendent of Education.

Cordeiro’s trajectory from student custodian to classroom teacher to system leader demonstrates not only resilience, but also a deep belief in the transformative potential of relationships and community. “Everyone needs to feel valued. Everyone needs to feel important. Their contributions have to be validated for the team to be working at optimum performance” he explained.

From the Classroom to System Leadership

Early in his career, Cordeiro discovered the importance of stepping into leadership roles even when doubt lingered. As a young teacher at a school in Oakville, he watched many experienced colleagues leave to open a new school, creating a leadership vacuum. Rather than retreat, he chose to step up. “You can go two ways. You can make yourself better or make yourself bitter,” he remembered. That choice to embrace challenge became a defining theme of his career.

As Superintendent, Cordeiro’s portfolio included elementary and secondary families of schools, safe and welcoming schools, and international student programs. He often spoke about the reciprocal nature of leadership. “As a system leader, I learn just as much or probably more from the persons I’m called to lead and the families we’re called to serve,” he said.

Relationships at the Heart of Learning

One of Cordeiro’s most consistent messages is that education is fundamentally relational. Whether as a teacher, principal, or superintendent, he saw trust and care as the true foundation for learning. “At the end of the day, your success is going to be determined by your relationship with that child. Do you create a safe space where that child feels they can come to you in their worst of moments and their best of moments?”

This emphasis aligns with research from the American Psychological Association, which shows that strong teacher-student relationships boost both academic outcomes and social-emotional well-being. For Cordeiro, this human connection was not just a strategy, but the essence of why he entered education.

Inspiring Innovation and Creativity

Beyond relationships, Cordeiro also fosters an environment of innovation. He emphasized that fostering creativity and innovation requires the courage to step outside of established norms. “You have to be creative, you have to be innovative… You have to step outside the box,” he explained.

His outlook resonates with the World Economic Forum’s Future of Jobs Report, which highlights that while automation may displace millions of jobs, even more new roles will emerge, requiring adaptability, creativity, and resilience. By encouraging students to pursue passion-driven projects, Cordeiro helped prepare them for that future.

Valuing Today’s Students

Perhaps one of his strongest challenges to conventional thinking is his defense of today’s learners. “Students today are far smarter than they were in the previous generation,” he said. “Their understanding of how the world works, their appreciation of each other, and their respect for diversity is unbelievable.”

In an era when students are sometimes criticized as disengaged or too reliant on technology, Cordeiro urges parents and educators to see their strengths. “Learn to appreciate that they’re learning differently. We have to invest ourselves in their learning because the jobs of today, the jobs of tomorrow, are going to be completely different than the jobs we walked into 10, 15, 20 years ago.”

Lessons for Educators Today

When asked what advice he would give his younger self, Cordeiro returned to the importance of relationships. “The stresses don’t matter because those moments with students are going to build your level of confidence. Those moments are going to raise your level of wellness so that the stresses become mitigated by the joys of the students in front of you.”

Even now, as he reflects on his career, he remains focused on vulnerability and impact. “Seize the opportunity. Seize the moment to give more of yourself and don’t be overly cautious about making yourself vulnerable, because it’s in that vulnerability that the relationship is forged with students, colleagues, and system leaders.”

A Legacy of Learning and Service

Anthony Cordeiro’s journey is a reminder that education is both deeply personal and profoundly communal. From his first Saturday mornings with a broom to his years in leadership, his legacy is one of service, resilience, and continuous growth. “Once you think you know something, the truth of the matter is there’s just so much more to learn,” he reflected. “It’s not title and position and leadership roles that necessarily speak to accomplishment, but how much you open your heart and your mind to the learning from others.”

For educators and leaders alike, his story is a call to embrace relationships, foster creativity, and never stop learning.