In Ed Woodward’s ideal world, he would be congratulating David Moyes on delivering the Premier League title. The midfield duo of Cesc Fàbregas and Thiago Alcantara – both signed early in the transfer window thanks to the combined convictions of Woodward and Moyes, inspire United to a 21st league success. A fit and happy Robin Van Persie ends the season as the Premier League’s top scorer whilst Sir Alex Ferguson, sat in the Sir Alex Ferguson Stand, smiles and applauds generously as the trophy is lifted in front of the Stretford End. The football was thrilling and the crowd was singing as a new era of dominance dawned at Old Trafford.

Unfortunately for Woodward the reality could not be further away from that dream. This season has been an unmitigated disaster at Old Trafford. Now Woodward is tasked with reversing the fortunes of Manchester United by having to make the most important decision at Old Trafford in nearly 30 years. Simply put, Woodward has to pick the right manager for Manchester United.

Then there’s the small matter of successfully recruiting United’s transfer targets, and after the debacle of last summer’s window he can’t afford anything resembling that shambles again. Take into account that this is also a World Cup year and it appears that Woodward has his work cutout for him.

Woodward is the man who advised and ultimately helped the Glazers complete their unpopular takeover of Manchester United. The club was saddled with a huge debt that, according to finance expert and United fan Andy Green, got as high as £753million in June 2010.  Since the Glazer takeover in 2005 United have reportedly seen as much as £680million flow out of the club in order to service the debt.

Woodward is also the man who masterminded United’s highly successful commercial strategy which saw the Red Devils become a massive money making machine. The on-pitch success delivered by Ferguson from 2005 to his retirement in 2013 (five Premier League titles, one UEFA Champions League, three League Cups, five Community Shields and a FIFA World Club Cup) has been matched by off-field triumphs with Woodward securing lucrative sponsorship deals for United.

Since Ed Woodward took over from David Gill there has been a shift in how the club have communicated with fans and a wider audience.  Shortly after Woodward assumed his new role United opened a twitter account – a small step, granted, but the club used it to initially break the news of David Moyes’ departure. Woodward has spoken with fanzine ‘United We Stand’ and met with key members of the Manchester United Supporters Trust (MUST) at his behest.  David Gill, it must be noted, cut off all communication with fan groups after the Glazer takeover. Woodward has also stated his desire to see ‘Football Club’ reintroduced into the club badge; a move that would no doubt please United fans.

Perhaps the most striking change is the willingness to brief the press about potential transfer targets.  Under Gill and Ferguson, any transfer activity was kept under wraps – just ask Javier Hernandez’s grandfather, who only learned about his grandson’s move to Manchester United when it was announced. Whether Woodward’s openness about United’s transfer activities with the press is a good idea or not is open to debate.

It’s fair to say that Ed Woodward knows how to secure lucrative sponsorship deals, but right now it’s his football acumen that needs to be spot on.  He’s not regarded in the most positive of lights given his closeness to the Glazers, his transfer dealings or lack thereof, and most recently United’s clumsy handling of David Moyes’ departure.  Woodward now has to step up and appoint the right manager for Manchester United.

The current favorite for the United hot seat is Louis Van Gaal and at the time of this writing, reports suggest that he could be named manager after the Red Devils’ final home match against Hull.  The only sticking point has been the composition of the backroom staff and what role, if any, Ryan Giggs and the rest of the ‘class of 92’ will have at Old Trafford.

However United are also reportedly on ‘red alert’ after Pep Guardiola’s comments about his position following Bayern Munich’s exit in the Champions League.  Add to that the apparent interest in Jürgen Klopp, Carlo Ancelotti and Diego Simeone – despite none of them having expressed an interest in the Old Trafford hot seat, along with calls for Ryan Giggs to be given the job permanently, and a seemingly clear-cut decision has become much less straightforward.

The more alarmist members of the United faithful may see parallels to the summer window insofar as the club being unable to sign their targets. The only player signed that summer was Marouane Fellaini in a deadline day fiasco.  Even the January signing of Juan Mata, good a player as he is, had a whiff of desperation about it.

In all fairness, the search for a new manager has left Woodward in an unenviable position of doing having to do due diligence whilst needing to act decisively to get the best man possible installed.  Even if Woodward does get his number one target, he’ll still have to deliver the players for the new manager.  Again, after last summer’s farrago nothing can be taken for granted until all deals are signed, sealed and delivered.

What Woodward can’t allow himself to do is dither, easier said than done of course, especially given the importance of this decision. The nightmare scenario would be to lose out on all the targets as a result of any procrastination. If United fail to appoint Van Gaal, Guardiola, Klopp, Ancelotti or Simeone, they could end up with Giggs being manager by default, and that’s if the Welshman would be happy to take on the job as United’s 6th choice.

This may be an overly pessimistic view of how things could end up at Old Trafford in the coming days and weeks.  In all likelihood, the nightmare scenario will never happen and there’s even the possibility of United landing all their targets.  The problem is that at the moment, there have been very few positives for United this season, and the key people post-Ferguson, current and departed, have not given supporters any reason to feel bullish about the prospects of seeing the world’s best talent arriving or trophies returning to Old Trafford any time soon.

More importantly, Woodward must be aware that his job, at the very least, is under scrutiny. If he gets this appointment right then he’ll be set in his role at United.  Get it wrong and Woodward will more than likely see someone else come in to replace him.

Sir Alex Ferguson, the football man, got it spectacularly wrong with his choice of David Moyes. Ed Woodward, the businessman, has to get this appointment right.  The Glazers won’t take too kindly if the value of Manchester United dwindles.  Woodward can’t afford to wait for the right manager to fall into United’s lap; he needs to be decisive and appoint his target quickly so that the next phase of the rebuilding process can continue.