The chances are the player may need a little more in the way of fatherly advice as the transfer window winds to a close and talk of interest from Blackburn Rovers gathers pace.
What can be said for sure is that the Ewood Park club were represented at Tannadice for this unlikely demolition of St Johnstone. It was certainly something of a surprise to see the Sky Bet Championship club skulking around Tayside considering their most recent acquisition from Tannadice, David Goodwillie, is back where he started, on loan after an abject spell south of the border.
Whatever Jackson said to Mackay-Steven, it worked. Shrugging off the disappointment of being omitted from the Scotland squad 24 hours earlier, the 22-year-old looked more like his old self, scoring one goal and setting one up for Stuart Armstrong.
Mackay-Steven has looked a little distracted this season and that is understandable considering many expected him to follow his old chum Johnny Russell, currently scoring goals for Derby County, to England this summer. He may yet receive an offer that satisfies his own ambitions and the demands of the Dundee United board, but needs to weigh up the pros and cons of making the jump now, especially given his previous lack of success at Liverpool
Would Blackburn be a good option at this stage in his career? Jordan Rhodes would certainly appreciate the service Mackay-Steven would provide from the left, but Rovers have won only one game in four so far and do not look like promotion material. Goodwillie's experience must act as a cautionary tale and Mackay-Steven has much to ponder outwith a Scottish League Cup League Cup visit to Dumbarton on Wednesday. "During the last few windows there has been speculation but I don't think too much about it," the winger said. "You hear stuff but you take most of it with a pinch of salt. My job is here and is about training and playing."
Goodwillie did score his first goal since his return in this match, adding to Keith Watson's deflected opener after a header from the defender looped into his path and gave him the chance to nod home. It was a crisp finish. There was definitely a sign of the predatory instinct of old as he stole a march on a static backline and an appetite that hasn't always been evident. Goodwillie still has quite a bit to go, though. While backed to the hilt by the United support, he looks short on confidence and has to show some sign that he has developed his game. "He took his goal well and his all-round play was a lot better," said manager Jackie McNamara. "He looked a threat and the goal takes a bit of weight off him."
Mackay-Steven then leapt to the fore when making it 3-0 just before the break with a clever finish from a tight angle and setting up Armstrong for the fourth with a ball in from the left. He insists being left out of the Scotland squad has given him a jolt and certainly backed up his words with actions. "In a way, being left out has given me more motivation," he said. "Everyone wants to represent their country and I have to be patient and keep my performances up."
For McNamara, the win was a real fillip and gives him a platform on which to set about turning Tannadice into the stronghold he demands in the wake of the side winning only four league matches there last term. The performances of young left-back Andrew Robertson, learning quickly after moving from Queen's Park, and Ryan Dow will have given him encouragement. "We had spoke since our last home game about how we need to make this place a fortress and that's a start," said Mackay-Steven. "I think the scoreline could have been even more handsome than it was."
Nigel Hasselbaink and Stevie MacLean missed late chances for the visitors, but Tommy Wright sensed a flatness about his side and has vowed to look at his own role in what went so wrong. "I didn't sense that flatness in the dressing-room, but I agree about it being the case on the pitch,' said goalkeeper Steve Banks.