In his new guise as Huddersfield Town manager, the class who he met for training on Tuesday morning are likely to have been demoralised as opposed to disruptive, but earning their respect and understanding will have to be similarly hard-earned.
The earlier working experiences of Cowley, an ex-head of Physical Education at a school in his native Essex and his brother and assistant Nicky – who was head of boys PE – are likely to come in handy in the weeks ahead.
Just as the pair built a winning mentality at Fitzwimaric School in Rayleigh – where their school sports teams won a number of national titles and finished fourth in the World School Athletics Championships in Prague in 2013 – so the Cowleys are now pursuing excellence in second-tier management.
To say they start off from a low base is an understatement. In anyone’s language, 2019 has been brutal to the Terriers.
Sensibly, the Cowleys, who quit Lincoln City to head to West Yorkshire at the second time of asking on Monday afternoon, are not making bold predictions.
But their desire to meet the challenge head-on is not something they are paying mere lip service to as they stay loyal to their working-class Essex roots.
On those early lessons from his teaching days, Cowley recalled: “I will forever be appreciative of the pathway we had. Our teaching backgrounds gave us the opportunity to build our skills-set.
“Addressing your naughtiest school classroom as your Friday period five – a year nine group – means you naturally learn to transfer skills across. People are people. Footballers are human beings and want to be successful and win and we have to remind them how.
“There will be no entitlement here. We value everything and humility is so important.
“First and foremost, we are in a relegation battle and there is no hiding place. We know the statistics for teams who have been in this position at this time of the season in the Championship. We’ve got to try and effect it.”
He added: “I respect it has been a really difficult period for the football club, but that excites me.
“For us, we want to wake up in the morning with that feeling and excitement and look at the job in front of us.
“Everybody at the club has been through the mill – this season and last season – and it has been really challenging.
“But the way the staff have conducted themselves throughout this period; you learn a lot about people in the face of adversity – they have been exemplary.
“The supporters have stayed with the players and management team and when things went well, they drove their energy and when they did not, they stood side by side.”
Just a day-and-a-half into their Terriers’ tenure and the commitment of the Cowleys is already unstinting.
Plans to move the family home to Yorkshire are already afoot. Local schools are being looked at – and they can count on their parents to follow them every step of the way on a match-day, just as they did in attending all of Lincoln’s matches without fail.
It is a team effort for the Cowley clan, just as it will need to be across the club if Town are to revive their fortunes and try and salvage something from a terrible year.
Having taken Concord Rangers up three levels from the Essex Senior League to the National League South and enjoyed two promotions at Lincoln, the Cowley managerial CV is striking.
A season at Braintree Town in 2015-16, which saw the Essex side secure their highest-ever finish and a place in the National League play-offs is another impressive tick in the box.
The surroundings are now more grand, but the principles are the same and just as the footballing brothers were given the dispensation to build the club in their own image as they did at Concord and Lincoln, so Town have acceded to that request.
It tipped the scales in their decision to join the club at the second time of asking after previously turning down a head coaching position last weekend.
Cowley added: “The opportunity to be managers as opposed to head coaches was really important to us. It is the way we have always worked.
“We spent eight years at Concord Rangers and built that football club from the bottom to the top and met so many good people.
“For us, it is the opportunity to be able to work in the way we work. We have some good successes and have always been able to do it in the way we feel.
“To have control over recruitment is very important to us.
“It is about building a football club and having the opportunity to effect the club, not just the players on the grass – from the academy right the way through to the community (level), which will play a really important part on the next step of the journey.”