Next came the onerous task of pacing the technical area during momentous matches at both domestic and international level. These days, the job description is decidedly more prosaic; while back in Mount Florida yesterday to give a seminar on positive coaching, the 53-year-old was also asked to adjudicate between two former team-mates on the subject of the vacant Scotland manager's role.
In the ongoing debate over who should replace Craig Levein, McLeish has already declared in favour of Gordon Strachan, but that doesn't mean he doesn't feel Billy Stark could also do a decent job if asked. It was McLeish, after all, who originally brought his former Aberdeen pal into the national fold, persuading him to leave Queen's Park to replace the departed Archie Knox as SFA youth teams coach. Should Stark embellish his cv still further with a victory as caretaker against Luxembourg tonight, his odds of taking the job on a permanent basis would shorten significantly.
"I'm sure if Billy was asked the question, he would have a big decision to make," McLeish said. "He's a great coach, someone I brought into the international set-up. He has a great way with the players and has done well with the under-21s. I brought him in because Billy had a wee bit of an aura about him, with the clubs he had played for and having done so well at Aberdeen, Celtic and St Mirren," McLeish added. "When he went into coaching with Tommy Burns, I heard a lot of good things about him through the grapevine.
"He can put his point across, he's a very good coach and he knows what he's talking about. I offered him the under-21s job because, with the younger players we had at that time, Billy had the necessary patience and the gravitas for the job. He's obviously in the Scotland system. And, if he's in the system and he's done decent things there, it stands to reason that he can be a credible candidate."
McLeish restated his feeling that his own immediate future is best served in club management – even if he has had no takers since leaving Aston Villa in the summer – and his belief that Strachan and Joe Jordan are the "outstanding candidates" to lead Scotland into the remainder of this campaign and beyond. If that is the medium-to-long term future for the country, the here and now will unfold under Stark's management in the Josy Barthel Stadium in Luxembourg City this evening.
Regardless of who is the manager going forward, McLeish feels there is more to come from this group of players. "The guys we have in the Premiership don't look out of place, not at all," he said. "Ten years ago, when I was in the job, we didn't have many there – Darren Fletcher, Davie Weir, James McFadden, Barry Ferguson maybe. But for me, the current crop are capable – individually they've shown great form in England.
"But I'm not blasting the players," he added. "They've come out and said themselves that they didn't do themselves justice in those four games. There's definitely something we haven't seen from these guys. At that level, a little more inspiration is required. Because you really are on the big stage, the whole world is on you and there is no hiding place – if you are a defender or attacker. But there are inspiring performances inside every one of these guys, performances that I don't think we have seen in the group."
Kenny Miller, with whom McLeish worked at both Hibernian and Scotland, has endured a difficult settling in period at Vancouver Whitecaps, but has crossed the globe to join with the squad for tonight's game. His old mentor McLeish remains a fan, but wonders if he may need to take up a different role in the squad going forward.
"Kenny has come all the way from Canada to join up again and he will want to play," said McLeish. "He'll be wanting to get on the park and show that he is capable of playing in the next international and World Cup qualifiers. But we do have to see the younger ones. Kenny is an elder statesman in there and, if he doesn't start the game, he could now be the guy who encourages the Jordan Rhodes and Steven Fletchers of this world."