Long before the glittering career that took him to the highest levels of the game: Steven Naismith lifted the SFA Youth Cup - and now he want his Wee Jambos to aim for the prize as well.
Our U18s coach lifted the trophy back in 2004 as a fresh-faced prospect at Kilmarnock: setting up the winning goal for Killie in a 1-0 triumph over Rangers at Rugby Park. It was a taste of things to come, of playing on the big occasions - and Naisy knows that his young guns will need to be at their best when Inverness Caley Thistle come to Gorgie tomorrow evening.
"The boys have been good in training ahead of this one," he told Hearts TV. "A few of the lads that have had niggles are coming back which means competition for places is high. It's good - the players know they have to be on it every day if they want to play.
"From being there as a young player myself and winning the youth cup, I know exactly how the experience can be and feel. If you can get through to the final with a chance of winning - that feeling is important.
"The competition is at a different level but, at this stage of their career, this is the biggest thing they can win. It's a great chance and a great opportunity."
His promotion to U18s coach since John Rankin's departure has seen Naisy renew the leadership qualities he so often displayed in a maroon jersey for Hearts, with the Scotland hall of famer keen to pass on the lessons from his experiences across his stellar career.
"I've always looked at youth coaching like this: take away the formation, the rotation and those parts of football. Our guys need to know where they can't afford to lose the ball. Where they can take risks. Where they need to be when they're out of possession.
"It's the general stuff. If they take a few years to get to the first team, the formation and system might have changed a few times by then. I'm focusing on the team dynamic: and if you do those things as a team, you can have success.
"One question I always ask myself when I'm coaching is; 'what was I like at that age?'. I never came through an academy as the biggest prospect - I had to work hard for it. That's what I'm trying to pass to the guys."
With fans welcome to attend the match for free, Naisy is expecting a performance in front of the fans under the Tynecastle lights.
"Occasions like this test their mentality much more than their standard league games. Everyone knows what the next stage after this is and that gives this match a different feel.
"It's got to be like this as much as possible for young players. Occasions like tomorrow are the only way to see if a youngster can handle the step to first team level. Playing in front of a crowd, at the later stage of a cup competition, is good."
Hearts U18s welcome Inverness CT to Tynecastle tomorrow night in the Scottish FA Youth Cup semi-final. Kick off is 7pm and admission is free. Back the boys as they aim for the final.