According to Steve Paterson, then his manager at Inverness Caledonian Thistle, the player had shown little inclination to knuckle-down and apply himself after his release from Rangers two years earlier, where Robson had failed to make a breakthrough.
When Paterson loaned him out to Forfar Athletic in 1999, the midfielder knew he had a choice: embrace the work ethic required of him, or else be left behind in part-time football.
Statistics show he adopted the former course of action and did so in spectacular fashion, returning to Inverness an improved performer before earning moves to Dundee United, Celtic and Middlesbrough. Robson would also pick up 17 Scotland caps along the way.
Now at Aberdeen, the 35-year-old is a considerably more mature individual than he was all those years ago in the Highland capital, which is probably why he refuses to become over-excited in the build up to today's Scottish League Cup semi-final between his Aberdeen side and St Johnstone at Tynecastle.
Indeed, with an almost dismissive air he smiles quietly in the face of questions about the expectations and pressure inherent to such cup ties. "All you can do is listen to the manager, work hard to focus on the day and keep the head down and concentrate on what is happening on the pitch," said Robson.
Those are steadying words from a footballer who saw the light on the road to Station Park in 1999. Robson has, of course, been brightened just as much by the prospect of reaching the final of his year's competition. The midfielder is nursing sore ribs - an injury suffered during his side's SPFL Premiership meeting with Motherwell last week - and stated yesterday that a couple of painkillers would be enough to get him ready to tackle whatever St Johnstone might throw at him.
"I missed a final with Celtic," he said. "I remember the surgeon saying I would be back in three weeks. Eight months later I was still out. That was frustrating, but I played in the final for Dundee United and lost to Celtic.
"I also qualified for a final with United but got the chance to move to Celtic. I missed out, but I got to play in the Champions League so I couldn't complain too much. I've played in quite a few semis but this is a trophy I have never won so it's something I'd love to do."
He is not the only one. Aberdeen will be followed by supporters who have tired of traipsing from one cup disappointment to the next and would much rather make their way into the final with minimum fuss. Derek McInnes, the Aberdeen manager, this week briefed his players to adopt a low-key public approach to their semi-final, despite a hopeful Aberdeen support - 13,000 will be at Tynecastle today - craving a first trophy win since 1996, when the Pittodrie side overcame Dundee to lift the League Cup.
"I do get a sense of the expectations up here," added Robson, who can expect to see new loan signing Shaleum Logan given his debut today in place of suspended Joe Shaughnessy. "I've seen it a lot over the years and it's something you can't allow yourselves to get caught up in because if might not work out on the day.
"There are expectations at every club, just more at some rather than others. You had it at Celtic, of course, but the were also expectations at Middlesbrough, which was really a Premiership-like club with a big budget trying to get out of the Championship. It was similar with Scotland.
"As you get older you know what can go wrong, but you just work harder to make sure it doesn't and try to help the younger guys through it. It would mean a lot to me [to reach the final], but no more so than at any other time in my career. When you start out in football you want to win things but there are countless players who go through their career earning a lot of money without winning anything. I've been lucky to win things and it gives you a taste for more."
Robson, signed by McInnes last summer following a short spell with Sheffield United, is impressed by the professionalism of a manager, who he played alongside at United. "I have played for a lot of top managers but he is up there with the best of them in terms of his preparation," he said. "He is still a young manager but, just like the top guys, he looks into everything. He has changed a lot of things here from the recruitment to the training. He's very much a modern-day manager.
"He is enjoyable to play for but you need to work hard. He is demanding every day, just like every top manager I have played for."