Auckland Grammar School Headmaster: The Truth About Teenage Boys & NZ Education System!

2025-07-09

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Tim O’Connor is the long-standing headmaster of Auckland Grammar School.When he started the job in 2012 he became only the 11th headmaster at Grammar in the schools 156 year history.In this conversation, Tim shares the highs and lows of his 13-years at Grammar. And his 10 years as the head of my old school, PNBHS, before that.This podcast offers a rare behind-the-scenes look at the culture, discipline, and deep traditions that define Auckland Grammar.We talk about everything from navigating r...

Tim O’Connor is the long-standing headmaster of Auckland Grammar School.

When he started the job in 2012 he became only the 11th headmaster at Grammar in the schools 156 year history.

In this conversation, Tim shares the highs and lows of his 13-years at Grammar. And his 10 years as the head of my old school, PNBHS, before that.

This podcast offers a rare behind-the-scenes look at the culture, discipline, and deep traditions that define Auckland Grammar.

We talk about everything from navigating risky behaviors and toxic masculinity to fostering mental resilience and identity in teenage boys.

Tim opens about his own path through education, the mentors who shaped him, and the leadership lessons he picked up at Harvard that now guide his everyday decision-making.

This is more than a conversation about a school. It’s a masterclass in leadership, vulnerability, and the future of education in a digital world.

It’s hard to think of many people who have done as much for young men in New Zealand in this century as what Tim O’Connor has done.

I enjoyed my time with Tim, and I think you will too.

***

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