"We've thought about it, and for boys' schools it's a big topic being discussed around the world.
"In other countries they're much more advanced in being prepared, than we are. In attending those conferences, we've realised we've been a little bit naive, and that we needed to prepare so it's not a shock."
When asked about the reaction from students, O'Connor said he thought adults typically underestimated where the younger generation was at.
"We're the ones who have bigger hang-ups about bigotry and LGBTQ".
He was also confident that homophobia at the school was improving
"Absolutely. The key is to name it and have conversations with the boys. The use of 'gay' as a colloquial phrase is present in our society, particularly amongst young people.
"When you name it and say you could actually be offending someone else - our boys have understood that, and we're seeing a positive reaction to it."