Now is the perfect time for Jackson to punt again, to get Roos to repeat his "Yes", this time to the question: "Will you coach Melbourne Football Club beyond 2015?"
On the September day last year on which he finally gave in to Jackson's plea and agreed to coach the Demons, Roos stressed he would be there for a short time only.
A time so brief that the watertight part of his lucrative contract states that there are only 35 more matches before The Sundance Kid moves on.
It is just nine matches old, but Roos' deal is 20 per cent completed.
Melbourne has been transformed since he took over. Roos has returned hope to the lives of supporters, replacing despair.
Three wins, three other near-wins, only one blowout. Percentage near 80, well up on 2013's reading in the 50s.
The recruits - Dom Tyson, Bernie Vince, Daniel Cross - are starring, not just on the field, but equally importantly for this club full of impressionable youngsters who have had confidence drained in recent years, off it.
Jack Viney would probably perform under anyone, but you feel he's going even harder because it's Roos who is coaching him. Jack Watts is showing signs of a breakthrough.
Cam Pedersen has been given responsibility, and has flourished. Jeremy Howe has added scope to his game. James Frawley has now got what he always wanted - a reason to stay.
The future, so bleak as recently as September last year, is now something to behold. All because of Roos.
It was the same when he took over at the Swans. Transformation was instant. Of the 10 matches he had as interim coach at the back end of the 2002 season after Rodney Eade exited, he won six, including the final four.
The next year, his first full season, he took his club to a preliminary final, a match in which it trailed the eventual premiers the Brisbane Lions at three-quarter time by just three points.
The Swans made a semi-final in 2004, then Grand Finals in the next two seasons. In his eight full years in charge of the club, only once did it fail to reach the finals.
Melbourne will not reach the same immediate success under Roos. But success is relative.
On the day he was announced to the public as Melbourne coach, Roos was well aware of the club's state.
"They're certainly not sugar-coating it - I know what I'm coming into. I know it's going to be a very difficult job," he said back then.
"I'm really looking forward to setting a direction for the players and the football club, and setting some really high standards."
He added Jackson had wooed him with a clear plan to appoint a coaching successor sooner rather than later.
"If there's success well and good, but if there's not ... I'm very happy for someone else to take the glory after that," Roos said.
"I'm sold on it (succession). It's the way football is moving forward."
Sydney Swans assistant Stuart Dew was unsuccessfully pursued for the succession role in the off-season.
As it stands, Roos has an option on the 2016 season.
Plans remain in place to have the next Melbourne coach on the club's books and working closely with Roos as soon as September this year.
It is a sound plan, and Brett Kirk, John Worsfold and Cameron Ling will be among those seriously considered for the role.
But given the extraordinary turnaround in the Demons' form during Roos' opening nine matches, the plan would work even better if the handover happened at the end of 2016, maybe 2017.
Now there's a real challenge for Jackson. Get Roos to extend for two years, through to the end of 2017.
