He and brother Danny have not become two of English football’s most highly-rated coaches by a conventional route.
Less than four years ago they gave up teaching for full-time football management, but it has not left them. A book called Are You a Proper Teacher? sits on the desk of their shared office overlooking Huddersfield Town’s training pitches.
As players, the London-born Cowleys never progressed beyond non-league, yet as joint managers of the Terriers – Danny is officially the boss, Nicky his assistant – they are coaching people like Danny Simpson, a former Champions League defender and Premier League winner.
It says a lot for the impression they made at Concord Rangers, Braintree Town and Lincoln City that they have been able to climb the footballing pyramid. Teaching PE forced them to look beyond their obsession and learn from other sports and people.
“My dad’s football mad and having a brother like Danny three years older, I was kicking a ball around for as long as I can remember,” says Nicky, who usually leaves interviews to his brother.
Neither’s body was quite up to playing top-level football for a living, even if their brains were.
“I played for West Ham’s academy before I moved to Charlton as a YTS,” recalls Nicky. “Just before the apprenticeships were handed out I suffered with Osgood-Schlatter (disease) in both knees, Danny suffered with it too.”
The influence of their parents pushed them towards teaching.
“We have really supportive parents – they still come to every game,” explains Nicky. “I wanted to try and make the grade as a professional but mum and dad said you need something to fall back on. The next best thing would be coaching football or teaching sport. I worked in a school in Upminster for two years before a job came up at the school Danny worked at. He was just becoming head of department at Fitzwimarc School in Rayleigh.
“They were 12 really good years. We were crowned national champions and went to the World Athletics Championships, which was a really good achievement for a normal comprehensive school. We had success in cross-country, basketball, football and rugby. We had 120-odd kids coming in before school started to do cross-country. That energised us.”
They were also playing non-league football, where Nicky was again drawn to work with Danny.
“Danny took the job as manager at Concord Rangers and encouraged me to sign,” he says. “It was lower than the standard I’d been playing but Danny had a good relationship with the chairman. We had eight seasons, some promotions and cups.
“I first picked up a knee injury when I was 17 and had a large part of my cartilage removed. When I got to 32 I had a microfracture procedure that took away some of my power, and I found it difficult to get to the levels I wanted to, particularly as we’d had promotions. Our assistant manager left and the timing seemed right.”
Running a non-league team alongside their day jobs required a fierce work ethic writ large over their office – literally. “If you can’t outplay them, outwork them” demands a slogan on the wall.
“We’re two lads who worked hard to earn this job and want to make the absolute most of it,” shrugs Nicky.
“To be successful you have to work incredibly hard and make a lot of sacrifices. We spend hours planning for each individual and the better your detail, the better the outcomes and experiences.
“As a teacher, you want to deliver good lessons and gain the children’s respect.
“You can only really do that if you’ve got an in-depth knowledge. Rugby, cross-country, athletics, basketball, badminton became a big part of our lives and we learnt from them.”
When Nicky was forced to give up playing, the Cowleys’ football careers went into overdrive.
“We finished the season at Concord just short of the (Conference South) play-offs and we’d probably taken Concord as far as it could go and as far as the chairman wanted it to go, which we were respectful of,” he recalls.
“We had a fantastic time at Braintree Town with really limited resources – we incredibly finished third in the National League with probably the smallest budget but we lost in the play-offs to Grimsby and moved to Lincoln.”
Their debut season at Sincil Bank, and first as full-time managers, catapulted them into the spotlight, less because the Imps were promoted back into the Football League, more from knocking out Ipswich Town, Brighton and Hove Albion and Burnley en route to the FA Cup quarter-finals.
Season two brought Lincoln’s first Wembley final, and the Football League Trophy, and season three promotion to League One before being spirited away by Huddersfield in September.
“The people we’ve met in the Championship have been very respectful,” stresses Nicky.
“Every person that’s started a new job, people probably look to see, ‘Show us what you’ve got.’ I’m not going to show the players my very best skills because my knee wouldn’t allow me.
“The most important thing is to show what your idea is, to show you’re a good person with consistent principles and values and then through hard work and commitment show you want to help the players improve. If they see things that make them better, they’re more likely to follow your ideas.
“A picture paints a thousands words so it’s good for players to spend time with us individually going through their (video analysis) clips.
“They sometimes come up with really interesting points that turn into ideas we can use.
“Teaching gave us some fantastic experiences, understanding human behaviour and man-management. You see all different types of behaviour and personalities and learn how to connect.”