"We didn't really know what was going on with her tantrums and challenging behaviour," said Hope Maihi, also mother to Taylor, 7, Jordan, 5, Terina, 2 and Anthony, 4 months.
"She'd wear dresses from kindy and steal them to bring home and we'd have a major battle trying to get them off her.
"She'd also take my tops to wear as dresses and wanted long hair more than anything else, so would put a pillow case on her head and pretend it was hair.
"We thought it might be a phase, but something in me knew it was more than that."
At age three, Ollie's parents allowed her to wear dress ups at home or at the homes of close friends, but told her that when she was out in public, she had to wear boy's clothes.
"It didn't last long because it made her so unhappy and we could see that.
"The behaviour got worse and so did her unhappiness."
Concerned, Maihi approached a doctor, who took the family down the path of ADD and behavioral testing, though nothing was found.
"I said no, there was something else and then we finally got a doctor to listen to us, who referred us to Child and Adolescent Mental Health services (CAMHS)."
CAMHS assessed Ollie and referred her to the Maori Mental Health team, which in turn referred her to an intern psychologist who, according to Ms Maihi, had no experience working with transgender children.
"It actually made it worse.
"The psychologist advised Ollie's school to treat her as gender neutral and suggested we put her in neutral clothes, which wasn't easy because it was hard to get pants on her because all she wanted was flowy clothes.
"When I told her that she had to use the boy's toilets at school, she sobbed and I thought that's it."
Having approached Ollie's school, Mrs Maihi asked them to either provide a gender neutral toilet or to let her use the girl's toilets.
"They were awesome and let her use the girl's toilets and in May this year, changed Ollie's gender on their records."
On Ollie's birthday last year, when the Maihis told her that she could finally dress in girl's clothes every day, she cried happy tears.
"I actually had a little cry to myself because it was a reality.
"I'd realised that stopping her from being herself wouldn't make her happy and it hadn't for such a long time.
"You could see the difference in her from the day we changed her whole wardrobe."
Maihi said the experience had brought mixed emotions.
"It's been very hard.
"I was always questioning myself and weighing up problems.
"Bryan and I wouldn't be able to be this supportive of Ollie without our own support from family."
Another influential person in helping them to understand their role as parents of a transgender child was Wellington pediatrician Dr Andrew Marshall.
Maihi said he had been "fantastic and so supportive".
"One of the biggest things he taught us was the importance of acceptance.
"When Ollie was telling us she was a girl, we'd say well no Ollie you're a boy but you want to be a girl, which was actually more damaging.
"In her mind, it was the truth but we were not accepting of who she was."
Ollie, who also battled significant hearing imparities until two and a half, as a result of undiagnosed glue ear, would be referred to an endocrinologist at age 10 to start hormone treatment.
Apprehensive of how other school children would eventually respond to Ollie's differences, Maihi held onto the fact that her daughter already had a close group of friends.
"At kindy, as a boy, Ollie always had girlfriends and she has three or four who have transferred to primary with her and accept that she's a girl now."
Mrs Maihi, a born and bred Waikanae local, last week started her own online support group for families of transgender children.
"I started the Facebook group The Real Me for parents going through the same thing and on the first day, I had 20 people join from as far as Wellington, messaging me a lot of their different stories.
"One of them was a parent newly going through it, so it's nice to be able to answer their calls at any time and have a chat."
Ollie, who popped into the living room mid-conversation to pass her mother a hand drawn card, set with roads and puffy pink clouds, proudly showed off her scuffed white heels before disappearing again.
"Ollie is Ollie and we love her for who she is and that's never going to change," Mrs Maihi said.
"You can see the change in her by looking back at photos.
"She's blossomed."