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“We’ve Always had a True Sense of our Values”: John Cunningham

Not many people can hold up childhood scrapbooks that point to their future career. John Cunningham can. He can still pull out a house plan he drew as a child, inspired by the ‘House of the Week’ column he read every week after school when buying copies of The Australian Women’s Weekly for his mother.

John Cunningham, Managing Director of Cunninghams Real Estate

In some respects, not much has changed for the Managing Director of Cunninghams Real Estate on Sydney’s Northern Beaches. “As a young kid, I would draw house plans. I’ve still got one of a house I designed when I was eight years old. I was also a kid who loved to talk, so houses and talking: real estate. There you go,” John recalls with a laugh.

Since he began in real estate at just 21, his career has been a constant “learning and growing exercise”. The real estate business is the trust business and his real commodity or service is people.

“The property component is just the third component to it, in my view,” he says. “I’ve always taken the view that my career has developed as I understand what my value is to clients and, therefore, what I’m worth to them. It’s really understanding where your value points are, where you make a difference, and then it comes down to how effective you are at influencing people to make good decisions.”

Despite dire predictions for real estate with the onset of COVID-19, Sydney’s – and Australia’s – property markets have boomed. John attributes that to the pandemic’s influence in turning people inward to their homes. They reassessed the meaning of their home to their lives and its value.

As a result, they became more valuable commodities. “That has driven sentiment and confidence to force the greatest boom we’ve seen in real estate in my career of 44 years,” John notes. That long career has seen booms and busts come and go, but the central tenets of operating a successful and much-lauded real estate business don’t change. At its core, it is a people business, he argues.

I’ve always taken the view that my career has developed as I understand what my value is to clients and, therefore, what I’m worth to them.

“It’s about bringing in the right people to your business,” John points out. “We’ve always had a true sense of what our values are, and making sure that we surround ourselves with people who share those values. And, yes, along the way you make mistakes and you learn from that. I think our success has been understanding how we can help people achieve their objectives.”

John is also Chair of the Pathway to Professional (P2P) initiative for the Real Estate Institute of NSW, an industry body of which he was president for two years. P2P is a formal structure to develop a more professional approach in real estate.

“It’s a journey. That’s why we call it a pathway; it’s not going to happen overnight,” he explains. “It starts in different ways across the industry, and I think there have been some significant changes.

“As a result, we forged reforms in NSW last year. We convinced government that we needed reform, so they increased education standards significantly.” Old hands will recall the advertising ‘rivers of gold’ in major weekend newspapers, which have largely disappeared as the internet took on the role.


Real estate has evolved with technology, but it is still very much a person-to-person facilitation. “Technology has dramatically changed what drives our business, but fundamentally, it is the same,” John says.

“A longstanding relationship must be built on trust, and the proof is in the delivery. I’ve always been of the view that if you want to develop long-lasting, trusting relationships, you’ve got to have transparency in what you’ve done. If you want to develop a relationship, you’ve got to know what you’re doing, and have the smarts and knowledge to actually provide that advice. You then have to deliver that and be able to execute the outcome.”

One relationship that has stood the test of time is with Rhys Rogers at Before You Bid, a company that provides a range of essential reports and assessments to John’s clients.

“Rhys had found an amazing niche in the marketplace that we were well aware of, and we just didn’t know how to fill it effectively,” he says.

“His product put in a piece of technology that brought it all together. Those integrations into our technology platform have been critical because it makes it easy for our clients to understand its benefits. It’s been a great relationship that has married into so many parts of our technology platform. We love working with guys like Rhys.”

Cunninghams Real Estate was established in 1991 by John and Ann Cunningham, and now has offices in Manly, Balgowlah and Dee Why on Sydney’s Northern Beaches.

John had a health scare about 14 years ago, which helped him focus on what was important in his life and in the lives of his team. He confesses that it changed the way he was working with everyone. It also changed his role and he found a passion for developing people, focusing on what he refers to as the three core values of the business: being principled, disciplined and responsible.

“These qualities are the cornerstones of our business. They form our DNA and our 20 key guiding principles that we work by. The fourth is, how well are we delivering our team values and behaviours to everyone with whom we are dealing?

“We instil in the team that this is how we work; this is what we call The Cunninghams Way. It’s an articulated document that fills in all those spaces,” he shares. John suggests that consistency is his primary leadership attribute, and a big part of being consistent is telling the truth. It was driven home by his father a long time ago.

“When I was a young man entering the world of real estate, my father said, ‘Always tell the truth. If you tell the truth, you never have to worry about anything.’ He was right.”

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