Those were the years when New Zealand's national provincial championship, once among the best in the world, was being downgraded to a semi-professional competition. So in order to boost his salary, Robertson, who had built his coaching foundations with the tiny Sumner club in Christchurch's sea-side suburb, would look for public speaking gigs.
They are likely to have been extremely entertaining. Later, after taking over as Canterbury's head coach, Robertson took great delight in breakdancing in the middle of the pitch following the Red and Blacks' championship victories; black suit and gradually receding hairline be damned.
He has a sense of humour, but his sense of timing is perhaps better. He was in the perfect position to push for his place as Blackadder's replacement last year - hanging his hat on the love his players have for him. The Crusaders' board bought it and what a good decision that has turned out to be.
The timing matters in other ways, too.
To put it politely, elite athletes have a finely-tuned sense for bullshit. They don't suffer fools, and Robertson, the 42-year-old surfer dude from Tauranga who got into the Canterbury rugby system when attending Lincoln University, is no fool.
Fluent in French and with knowledge of Japanese after playing for Perpignan and Ricoh Black Rams, respectively, Robertson coached the New Zealand Under-20s to a world championship in Italy in 2015 and is more worldly than he likes to let on.
In an interview after being appointed Blackadder's successor in the middle of last year, Robertson said he wouldn't be changing his style, and the sometimes staid rugby world is better off for it.
"This is me," he said. "This is the way I have played and coached, as well. The guys have seemed to embrace it. It is just the way it is. They will know if I am pretending. I will just continue to be myself.
"I feel really privileged to do this. I gave the board a clear vision of how I would like to continue that success. I have got my own personality, and that's who I am."
This week, as the Crusaders prepared for their final against the Lions in Johannesburg tomorrow (2am NZT), assistant coach Brad Mooar spoke of Robertson's energy being his point of difference. But Mooar added Robertson could be demanding, too.
"He knows the game and is very clear on how he wants it to be played," Mooar said. "The group is very happy. It's an enjoyable team to be a part of and we can have a laugh but it's well understood that the expectation is you do the work so nobody shirks anything there and Scott's included in that."
