He started with Courts just short of two decades ago as a buyer, and worked his way up to the CEO spot backed by a series of mentors and supportive bosses along the way.
"I think it's very important for a CEO or for any senior figure within a business, really, to have a peer network outside of the business and people that they can confide in and that can act as sounding boards, mentors," said O'Connor.
"Just as a CEO needs to be a mentor, they need to have mentors as well. Because there will be difficult moments along the way and there will be times when you question yourself."
Speaking at an SAS/NUS Business School Alumni breakfast, O'Connor said having that support network was important during recent challenging times for Courts.
It's important to bring people along with you to be very democratic about sharing information
CEO Courts Asia
The parent company in the UK had collapsed and the Asia business, which at the time included Singapore, Malaysia, Thailand and Indonesia, was sold to private equity investors.
O'Connor said it was a scary time, but also liberating.
"Clearly some of the opportunities and challenges in Southeast Asia, particularly in the consumer electronics space, weren't consistent with who our parent company was as a UK furniture retailer," he said.
Looking at the operations in the region, O'Connor said it became clear that although Courts was one company, it was running four "massively" different business with varying operational performances and management structures, and very limited best practice.
"There was no regional structure in place to synergise," he said.
Working with consultants, Courts Asia developed a turnaround plan that included shutting down the operations in Thailand and getting out of Indonesia for the time being.
For the remaining stores in Singapore and Malaysia, Courts Asia shifted the focus more toward consumer electronics than furniture.
Now that it's on a stable footing, the company has plans to grow. It aims to expand to 18 stores in Singapore and 95 in Malaysia by 2015. It's also considering getting into a third Southeast Asian country, most likely Indonesia, with its vast consumer market.
O'Connor was asked if he ever had moments of doubt about the plan.
"I don't think there's a decent CEO anywhere that will not have those moments," he said. "Those moments come with the territory. It's a bit of a cliché to say it's lonely at the top, but it is."
Lonely maybe, but he's not alone. O'Connor is involved in a number of peer organisations, including the British Chamber of Commerce and the Young Presidents' Organisation (YPO), an international grouping of under-45 corporate executives.
He says he can tap into that network when faced with new challenges within his own organisation.
"Clearly within YPO everybody's a CEO or Chairman and obviously some of those CEOs manage much bigger businesses than I do, so I can get skills or learnings imparted from them managing much more complex organisations."
The turnaround saga has also reinforced for him the importance of imparting his own "learnings" to those who might look to him as a mentor.
"I think it's important to bring people along with you to be very democratic about sharing information, to be very inclusive about people's contribution to the plan so they see it very much as 'we're in this together and it's our plan.' And therefore they build in their own accountability for execution because it came from them. "
O'Connor is also very big on getting his message out to the media in order to build the brand.
"You've got to be prepared to talk about what you're really, really good at. You've also got to be prepared to talk about things that go wrong. And I think we've built that reputation for transparency because no subject's too hard to talk about," he said.
The retail environment in general and Courts Asia in particular have changed dramatically during O'Connor's career. For example, he says Courts Asia now relies less on traditional marketing and more on social networking.
It also took a chance on opening megastores, feeling that the market was ready for them. And the company invests more in training than it ever did before.
O'Connor says he's had to change, too, using a football analogy to explain the transition.
"As business has got bigger you have to transform yourself from the star striker, the guy who gets the business done to someone who's far more interested in managing, developing, sourcing talent and they get the business done. So your role changes from a star striker to head coach."
As the coach, O'Connor knows that the team won't be perfect. He says he doesn't lose sleep over that.
But he says he will lose sleep over making sure the team is responding to changes in the market place and putting in best practices to limit mistakes. And when a mistake is made, making sure they're really sharp in recovering.