Scottish Football Association director of football development Jim Fleeting has witnessed Villas-Boas' rise from a 17-year-old novice to the hottest young manager in the game.
Villas-Boas secured his C licence, B licence, A licence and Pro-Licence under Fleeting's tutelage at the now-famous Inverclyde National Sports Centre in Largs, where Jose Mourinho also gained some of his qualifications.
And although Fleeting could have never predicted the meteoric rise that today saw Mourinho's protege appointed as Chelsea manager at the tender age of 33, he did see all the right ingredients in the Portuguese prodigy for him to be successful.
"What he did have is a determination to be the best he possibly could be," said Fleeting.
"He had a drive to find out as much as he possibly could about the subject he was dealing with.
"He had a great attention span, he was a very good listener, and he was very good at putting things across on the field.
"These are the kinds of skills that good coaches have."
Fleeting recalls little of his first meeting with the teenage Villas-Boas, other than noting a particularly "young boy" was on his course.
But as Villas-Boas kept coming back to Scotland, Fleeting got to know him personally and professionally.
"Andre was very, very good," he said.
"He was very good at sharing with his other colleagues.
"I actually use him as an example. I've used him in the past two courses. One he delivered personally, and in one I used his presentations."
Indeed, Fleeting is considering inviting Villas-Boas back as a guest speaker, an honour usually reserved for the likes of World Cup winners such as Carlos Alberto Perreira and Marcello Lippi.
But despite possessing the same drive as Mourinho, any Chelsea fans expecting Villas-Boas to anoint himself as the new 'Special One' should be braced for disappointment.
"He's quite humble in his achievements," Fleeting said.
"It's nice he has that humility and respect for others."
He added: "Andre is his own man and I'm so pleased that he's his own man.
"We're happy for Andre and his family that he's successful, as we are when we see other coaches come on our courses and do very well.
"We still have contact with them all. There are none of them that you can't pick the phone up and speak to.
"We're a small country, we work hard at what we do, and these guys remember their roots, which is so important to us.
"People keep coming here for some reason - it must be the weather!"
While still undertaking his coaching badges, Villas-Boas got his first job in management, a short stint in charge of the British Virgin Islands.
Avondale Williams played under the then 21-year-old and is now head coach of the team himself.
"We thought he was a youth coach when he first arrived!" said the former striker, who is a week older than his ex-manager.
"We thought, 'Who's this kid?'
"When we started working with him, we saw he had a very good knowledge.
"He brought forward a lot of ideas when he came in, considering he was younger than us.
"He taught us about using our individual skills to become a team and become winners."
That did not translate to results on the field but Villas-Boas impressed enough for Williams to use many of his ideas during his own coaching career.
"I've managed a local club and used many of his techniques and tactics and am implementing them in the national team," he said.
"We got quite good ideas from him."
Source: Team Talk
Source: Team Talk