"I wasn't expecting to win -- it was a very close competition."
It was the second time entering the awards for Mr Bailey, who does not come from a farming background.
He moved from the United Kingdom to Wairarapa at age 9, after his father, a geography teacher, landed a job at Chanel College in Masterton.
It was when his parents bought their house in rural Carterton that, as a 13-year-old, he first developed a "thirst" for milking. Since then, he's been "hooked on it".
"The house was surrounded by a dairy farm. I would see the farmer milking the cows and thought, 'that looks cool', so I asked him if I could learn from him," Mr Bailey said.
"That led to getting relief milking jobs on other farms all through high school and in the school holidays. I got a real thirst for what it was about."
After attending Carterton Primary School and Chanel College, Mr Bailey explored career options such as joining the NZ Defence Force and the police force.
"But I found dairy farming stuck out for me -- it was in line with a lot of my interests."
He describes himself as a "very outdoors person", having played football during high school and now refereeing the sport.
"For me being outside is a lot better than being stuck in the office. I'm an active person -- I can't sit still for more than five minutes."
Mr Bailey, who has been milking cows in Greytown since 2014, aims to progress to a managing role within the next few years.
He is "exploring the business side" of dairy farming while studying for a Level 5 certificate in primary industry production management.
Head judge of the category and Hawkes Bay dairy farmer Nikki Halford said Mr Bailey was able to articulate ideas on some of the issues facing the industry.
"He stood out. He talked about wanting to get some consistency in employment standards across the industry in terms of rosters, in retaining staff and understanding what it takes." She also said he was mature and active in NZ Young Farmers.
Mr Bailey walked away from the awards with $10,500 in prizes.
Lance Graves, a Martinborough herd manager, and Mark and Jaime Arnold, from Dannevirke, were also recognised for their work in the industry, all winning awards.
Mr Graves, 26, came third for 2016 New Zealand Dairy Manager of the Year.
He also won the Westpac Financial Management & Planning Award.
The former diesel mechanic took away $6000 in prizes.
The Arnolds took away the supreme award, being named the 2016 New Zealand Share Farmers of the Year.
They also won the Ecolab Farm Dairy Hygiene Award, the Ravensdown Pasture Performance Award and the Westpac Business Performance Award.
They are 50/50 sharemilking 500 cows for Mike and Sherynn Harold, and Stuart and Sandra Cordell, in Dannevirke.
The former logging crew manager and teacher received $52,000 in prizes and cash.
