The problem is magnified for Kevin Keegan at Wembley Stadium tonight because he has 90 minutes to play with. He also has attacking instincts and it was clear, after training yesterday, that he was torn between sending his England team out to do a job, and asking them to go out and put on a show.
Not that a two-goal disadvantage is a better position to be in. Craig Brown, whose Scottish team lost by that score in the first-leg of the European Championship play-off at Hampden Park on Saturday, has to decide whether to risk all-out attack or adopt a more cautious approach.
Yesterday he was uncharacteristically "up and up 'em" as he said "anything loose is ours" and "50-50s are ours". He added: "Everything is not perfect in England's defence, they can be attacked, particularly in the wide spaces. We would like to put them in a losing-lead situation where they don't know whether to try and score themselves or hold on and defend."
Keegan faces that dilemma already. So far, unexpectedly, his teams have been hard to beat and, too often, hard to watch. Though unbeaten in eight matches - they have won four - they have not dominated a match since the 3-1 win over Poland in his first match.
Is this, then, he was asked, "an opportunity to go out and seize a game and really take it to the opposition, or a case of getting the job done and working on the more expansive aspects afterwards? "They've got to find a way of doing both," replied the England manager. "Go out, do a professional job, finish off what they started on Saturday. Also, it is a chance in front of our own fans to give them, and some of you people [the media], more belief that we can go on and not just go to Holland and Belgium, but go there with a winner's chance. It will certainly not be our intention to go out there and think that 0-0 will suffice.
"We worked really hard for the opportunity to get in the driving seat. Now we've got to drive. If we don't do that then it will be a terrible waste of an awful lot of effort."
Brown, ever the optimist, and ever the professional, has had his team practising penalties, but the odds heavily favour England. They may not be very good at penalties but first Scotland have to take them that far.
England have not conceded more than two goals in a match since Brazil defeated them 3-1 at Wembley four years and 50 matches ago and they have not conceded more than one to the Scots since 1977.
The visitors' cause is not helped by the suspension of Kevin Gallacher, after his booking at Hampden, and a calf injury to Don Hutchison. The Everton midfielder appeared to have successfully come through yesterday's training session at Wembley but it is understood he has internal bleeding and Brown is wary of him breaking down during the match. Not only might that leave Scotland short in a match they hope to push to 120 minutes, but it might also cause a repeat of the dispute Brown has had with Kilmarnock after Ian Durrant broke down in similar circumstances in the Czech Republic last summer.
Colin Cameron is the likely replacement for Hutchison, though it is conceivable that both may play with Hutchison being pushed forward to give the attack an aerial presence. Alternatively, Neil McCann may partner Billy Dodds and attempt to drag Martin Keown and Tony Adams into wide areas. Brown noted that they were caused difficulties at Wembley in Arsenal's Champions' League games, though his mention of Gabriel Batistuta's goal only highlighted the contrasting poverty of Scotland's attack. There may also be a change on the left with Callum Davidson, or possibly McCann, in line to replace Paul Ritchie.
Keegan would like to name a similar side to Saturday but has a doubt over Keown, who has a calf injury. Gareth Southgate stands by to deputise. Keegan will give the Arsenal player as long as possible to try and prove his fitness. "I want to give him another day and he has a good record of recovering. I won't risk him if there is any doubt," Keegan said. The only other change could be in attack where Andy Cole may start instead of Michael Owen. "If it is not broke I'm not going to fix it," said Keegan, adding, in reference to Jamie Redknapp's exile on the left flank, "Jamie got better on the left as the game went on."
For all Keegan's attacking enthusiasm, England's approach will be determined, once the game starts, by the mood of their senior players. "What we have, we hold" is the standard outlook in such situations and their gameplan will probably be dictated by the Scots. If Scotland attack from the off, England, initially at least, will pull back and look to hit them on the break. If Scotland sit back, England will push on but do so cautiously.
An early goal for Scotland would make for the most exciting occasion and, all the time England do not score, there will be tension. However, it is hard to imagine England letting slip the tie now. Should they do so even those "Bannockburn 1314" banners may finally be consigned to history and a new set printed, bearing the legend "Wembley 1999".
Scots wizards, page 30
Irish dilemma, page 31
Four teams will progress via the play-offs to next summer's Euro 2000 finals: the winners from the two-legged ties between Scotland and England, Israel and Denmark, Slovenia and Ukraine, Republic of Ireland and Turkey.
In the event of an aggregate draw, away goals will count double in the play-offs. If the scores are level after both games and no team has an away-goal advantage, extra time will be played. If the tie has still not been decided, the match will go to penalties.
TEAMS ALREADY QUALIFIED FOR FINALS
Belgium (co-hosts), the Netherlands (co-hosts), Czech Republic, France, Germany, Italy, Norway, Portugal, Romania, Spain, Sweden and Yugoslavia.
Draw: Sunday 12 December.
Finals: 10 June to 2 July 2000.