Tim O'Connor admits there have been a few awkward moments during his first days as headmaster at Auckland Grammar.
It has been two weeks since he arrived from the rival Palmerston North Boys High School, where he was head.
"I was reading out the cycling results for nationals in assembly. I got to second place and it was a Grammar student. I got to first place and sort of paused.
"I read it out - from Palmerston North Boys - and there was just this silence.
"I slowly looked up, smiling, and everyone in the room started laughing."
At 44, he is a young headmaster. He was only 34 when he was appointed rector at Palmerston North Boys and says the decision to apply for the top position at Grammar came from a want to walk the talk.
"I thought applying to this job was really about a challenge. It's something that I've always said to the boys, to avoid soft options.
"When this job came up, I thought: 'I probably should have a crack at that' - because of that philosophy I'd shared with the boys.
"When I explained to them that it was about seeking new challenges and personal extension, they understood that."
Mr O'Connor grew up in Palmerston North and is an old boy of the school he headed for a decade.
In 2007 he received a Woolf Fisher Fellowship and was awarded a Sir Peter Blake Trust Emerging Leader award the same year.
His wife and two young children, aged 5 and 9, have moved to Auckland with him.
His 15-year-old son will finish the schooling year in Palmerston North before starting at Auckland Grammar next year - something his father says will test him.
Mr O'Connor is still in touch with former principal John Morris, who he has known for many years.
"I've had a lot of respect for what John's done here. There are still things that I require his expertise and his intellectual knowledge. He's got Grammar in his blood now and he wants to see the place grow and succeed."
Mr O'Connor's approach is to first understand the Grammar culture and provide a fresh perspective with the hope of maintaining the school's position as one of the best in the country.
He hopes to bring his own insights, but the main goal was for good men to graduate from the school.
"Whatever we do whether it's academia, sport or just the characters that walk out of our gate after five years here, that they are quality citizens that are going to contribute in whatever their area is."