In a far cry from the luxuries of the England squad, the attacking midfielder could be found in the car park with a sponge and bucket of soapy water.
Pressley told the 'BBC': "We would get the young players to tidy the changing rooms and clean the senior players' boots - and if I felt James had done something wrong, he would wash my car."
However it was not hard to recognise his "outstanding technical ability" and he was given his debut as a 17-year-old.
"He was 16 when he started training with the first team and didn't take any time to feel his way in. He was confident in his ability and he felt like he belonged there," added Pressley.
"It wasn't a case of shaping his ability, because he had been born with that. It was about shaping him as a young person, and as an individual, into a footballer who could perform season after season.
"It was about making sure that self-belief and confidence didn't start to become arrogance."