Since Alex Ferguson had thrown him in at the deep end for Aberdeen against Rangers after Willie Garner had broken a leg in a 1978 European Cup-Winners' Cup-tie in Bulgaria, he had walked with success and he didn't like what was happening at Fir Park.
On this particular Saturday, McLeish, who would, of course, later manage Hibs, had watched his side defend soundly for the most part, attack with dash and end up with nothing to show for it. Motherwell didn't look at all bad, but they found themselves languishing in the sump of the Premier Division with only Kilmarnock below them.
"And so it continues," he said, after Hibs had emerged from a nightmare of their own to get back on the rails at his side's expense.
"Our heads won't go down - I don't give up that easily. Little things are hurting us." He had meant things like missing open goals and having the odd lapse at the back, but there was also that familiar malaise which afflicts every side except, at the time, the well-heeled Rangers - a chronic shortage of manpower.
With key men such as Tommy Coyne and Brian Martin unavailable - the latter had a hamstring injury and might have been lost to the cause for three weeks had he been risked - the situation became fraught. On top of all that, there was the awful tightness which grips players who know that things are getting desperate. This anxiety almost certainly played its part when John Hendry blazed over from close-range when Hibs led by a single goal.
Alex Burns, Dougie Arnott and Shaun McSkimming were all denied by goalkeeper Jim Leighton, whose form at the time continued to border on the uncanny.
Hibs made few real chances and took two, while Motherwell made many and took none. The Edinburgh side were aided by an inspired return from injury by Keith Wright, whose power and awareness enabled him to nod away a header sent across goal by Andy Millen and then soar to bullet home a superb cross by Michael O'Neill who had turned Miodrag Krivokapic quite beautifully.
Hibs produced flashes of the play which had taken them to their healthy position in the table and their manager, Alex Miller, was encouraged by the showing of Pat McGinlay, victim of a virus during the week leading up to the match.
Darren Jackson hadn't allowed the side's recent woes to affect him and was again sharp as a tack. There was makeshift look about the defence, but Hibs too were caught in the injury trap and could only weather the storm. Their cause wasn't helped afterwards by a three-match suspension for O'Neill.
Motherwell (3-5-2): Howie, Krivokapic, Richie, Denham; McSkimming, Lambert, Dolan (Hendry 42), Roddie (Davies 72), McKinnon; Burns, Arnott.
Hibs (4-4-2): Leighton, Millen, Hunter, Tweed, Dods; McAllister, C Jackson, McGinlay, O'Neill; Wright, D Jackson.