Indeed, as Ryan Kent blossoms in blue, the Hibernian head coach has ample cause to feel a sense of pride.
Always considered a promising prospect as he emerged through the youth ranks at Liverpool, Kent truly announced himself in the senior game during a profitable loan spell with Barnsley during the 2016/17 campaign.
Heckingbottom, Tykes manager at the time, put his faith in the winger – still a teenager at the time – by handing him key responsibilities on the flank and trusting him to be a pivotal part of the side as they sought Championship survival.
Kent made 43 appearances that season, helped Barnsley secure a laudable mid-table berth and was named their young player of the year.
More than that, Heckingbottom believes he finally illustrated the ‘quirky’ personality and self-assurance that would allow him to be a stand-out at a club of Rangers’ stature.
“His time at Barnsley helped to bring Ryan out of his shell,” said Heckingbottom. “He’s a quiet boy and just loves his football, but we really began to see his personality there.
“It’s too easy for people to say ‘oh, with such a young team, they won’t take responsibility’ but how do you know if you don’t give them any?
“So, he was really, really pushed in terms of that, his role on the pitch and what was expected of him – and he responded.
“He was a big part of what we were. We used his pace a hell of a lot in how we countered. We used him as an outlet and we asked him to stay wide if we had a narrow one on the other side. “We pushed him on his defensive work and his end product. We identified his strengths and what we thought were his weaknesses in terms of what we were looking to improve and that was very much in line with Liverpool.”
Such was his progress at Oakwell, Liverpool fought off interest in his services and handed Kent a new long-term contract and, with five goals in 34 outings to date this season, Heckingbottom suspects Reds boss Jurgen Klopp, pictured, will be keen to assess him again during the summer.
“I know that when his loan was up with Barnsley there were some really good clubs looking at him, but Liverpool were keen to tie him down and keep him,” continued Heckingbottom.
“I’m sure there will be a plan for Ryan and he will be involved in that with his representatives and Liverpool.
“That could be another loan or a permanent move or it could be as part of the Liverpool squad because I think they will definitely have another look at him when he does back in pre-season.”
While Heckingbottom knows all too well the challenge of shackling Kent, he is loath to focus solely on his former charge as he aims to mastermind a victory over Rangers under the Friday night lights in Leith.
Nevertheless, he hopes a memorable triumph could be the catalyst in his bid to have Hibs belying budgets and battling for silverware in Scottish football.
“It’s pretty apparent where the financial power lies and everybody is aware of it,” he continued.
“But our goal is to be competing with those big clubs; competing for cups, competing at the top end of the league and this is where we start.”
Heckingbottom does, however, acknowledge that his side will need to be more industrious in possession than they were during a diligent, but ultimately impotent, Scottish Cup defeat against Celtic last Saturday.
“If you look back at the Celtic game, both keepers had very little to do,” he added. “We had a couple of shots on target, they had three.
“Their keeper [Scott Bain] made a couple of easy saves, Ofir [Marciano] makes one in the first half, then we conceded two.
“Apart from that, we were strong without the ball. However, we were wasteful with the ball. We need to be better in possession”