It even persuaded the Australian prime minister that he should tail her for a week, capturing the candid moments usually reserved for insiders.
The resulting photo essay earned him a Walkley and two PANPA/Canon awards last year, and admiration from colleagues across the industry.
But it was a love of backyard cricket, not politics, that led Hillyard to photography. That and football – and maybe tennis and baseball, too.
“I was sports mad,” the 39-year-old photographer confesses.
“But I realised at some point, I was not going to be good enough to make it as a pro sportsman. So I thought, ‘why don’t I take pictures? That’ll get me into the sports events for free’.”
What began as a teenager’s scheme to watch sport became a lifelong passion and career.
At 13, his mother returned from a trip abroad with his first camera, a brand new SLR.
Even at this young age, he was an avid reader of the now-defunct Adelaide News
“Since then, photography has been a part of my life every day. It was a hobby that turned into a profession,” he says.
He graduated high school at 17 and took a job in the now-defunct Adelaide News darkroom: “The News was the sports paper, so it’s what I read as a kid,” he recalls.
There were no guarantees, but his hard work was rewarded with a cadetship.
Yet his biggest break came when the newspaper closed in 1992.
Fresh out of a job, Hillyard decided to spend a day at the Oakbank race meeting, and took along a borrowed camera.
He was on the barriers watching as jockey Simon Mills fell from his saddle, was caught in his stirrups and dragged down the straight.
The incident made headlines around the world.
“Once something makes news around the world, people want the pictures,” he says – and he had a whole set.
The photographs earned Hillyard enough money to kit himself out and begin working freelance, before joining the Adelaide Advertiser as a news and then sports photographer.
He made the move to Sydney’s News Limited tabloid, the Daily Telegraph, in 1998 – perfect timing for the 2000 Sydney Olympics.
The plan was to stay for two years but he’s been on the paper ever since – which is where the prime minister comes in.
“I got a phone call,” Hillyard laughs.
“I was in here doing a sports shift, as I generally do, and my picture editor asked, ‘it looks like we can get some access with the prime minister this week – are you in a position to go down and do it?”
A week with Australia’s leader is a big assignment. But this week was special.
It was late June 2010, and Julia Gillard had just ousted Kevin Rudd in a dramatic spill that caught global attention.
Australia’s first woman prime minister was hot property.
“I was happy to give it a go, but it was something that was foreign to me after spending years and years and years doing mostly sport,” says Hillyard.
“Parliament House to me was the big building on the left as you drove down to Canberra stadium from the airport.”
Hillyard took his opportunity, travelling with the Prime Ministerial entourage for five days.
But he wanted a meeting with her before the project began.
“I started by talking to the press officer but he didn’t think that was possible. And I said, ‘look if I can’t get to talk to her, I probably can’t start the series.”
Hillyard got his meeting.
“I was a bit nervous,” he remembers. “I actually showed her some of my personal work that I’d done in black and white, so I think that showed her that I knew how to handle a camera.”
The meeting meant an opportunity to gain her trust, and in turn, a level of access other photographers were denied.
The back seat of the PM’s car is usually off limits to press. But Hillyard was allowed to travel beside her, and captured one of the most iconic shots of his black and white Gillard series.
“She had to make a phone call to [former prime minister] Bob Hawke at the time, and she just went about her job, and I went about mine,” he says.
“Being a sports photographer, and thrown into an assignment like this, I just had fresh eyes.”
At heart, Hillyard remains a sports photographer. He has three Olympics and a dozen tours with the Australian cricket team under his belt.
But photographing cricket is a totally different ball game to following the prime minister.
“To be a cricket photographer, the number one thing you need is patience,” Hillyard says.
“Sessions are two hours each and the news story of the day can happen at any one particular ball out of the 90 overs of play during the day.
“And you’re supposed to have that picture. So I guess it’s a good thing that I love cricket.”
If endless hours of waiting for ‘the shot’ have honed Hillyard’s patience, it’s likely his early days in Adelaide News darkroom sharpened his eye.
“I remember one of the senior photographers said to me, ‘What you need to do, son, is look at everybody’s work, and look at how they work, and you need to pick out the best part of every photographer that’s in this place, and take it and learn from it’.
“And he said, ‘if you can do that, you’ll be better than all of them’.”
But taking lessons from other photographers only goes so far, he says.
“You can learn a lot of things from others but photography is about seeing. Only you can teach yourself that.”