When Mourinho read reports that Woodward had decided to hire a technical director, he demanded to be told it wasn't true. The implication was that he feared his power would be watered down; Woodward insisted it wasn't, knowing very well that making an appointment of that kind would be much easier once Mourinho had gone. That was six months ago.
Solskjaer has not been afraid to admit the size of the rebuild he faces after watching his team finish sixth in the Premier League, a mammoth 32 points behind champions Manchester City. The problem, though, is that other than the manager, not much has changed. The way United buy players is broadly similar to a year ago. And last time, it did not go well. Instead of bridging the gap with City, they went backwards.
A repeat this summer would immediately put Solskjaer on the back foot ahead of his first full season in charge. After the last campaign ended with eight defeats from the final 12 matches, he needs a flying start.
Why is it taking so long?
Woodward's plan for a technical director is to hire someone capable of overseeing the football side. In his mind, it is someone who can deal with first-team recruitment while also having the foresight to buy a teenager and organise a loan with the right club to fit his development. There are other issues that this person would need to address, some of them in embarrassingly simple areas such as maintaining clear communication with United players.
For example, Ander Herrera was left panicking about his future last summer after hearing nothing from the club about whether they planned to trigger a one-year extension in his contract. He received a letter notifying him of the renewal only five days before his deal was due to expire.
In the middle of contract talks this season, Herrera heard nothing from United for three months. It was only after Solskjaer was appointed permanently in March that he was made an offer, but by then it was too late. Sources have told ESPN FC that the lack of communication was a major factor in Herrera's decision to leave this summer.
The confusion surrounding Herrera is not an isolated case. A prominent academy player was left stunned after United did nothing about securing his future until weeks before he was due to become a free agent. "He had more attention from the rest of the top six and the biggest teams in Europe than from his own club," one source told ESPN FC.
It's vital to get this right
Woodward would like the technical director to help join the dots and link the management team with the recruitment team and the academy, but it is easier said than done. While there have not yet been significant structural changes at Old Trafford, one thing that has changed is Woodward himself. There has been an acceptance that while he has been a skilled businessman in driving the corporate side of Man United, different talents entirely are required for the rebuild.
Executives across Europe have been consulted, and experienced sporting directors like Andrea Berta, at Atletico Madrid, and Monchi, at Sevilla, have been considered. However, the fact that Monchi, considered one of the best sporting directors in the world, left Roma during United's search suggests Woodward is keen to go in his own direction. He is keen to install someone who fits the culture at Old Trafford, nurturing young players to fit a style of football that is built around pace and incision.
Woodward has met with Rio Ferdinand, feeling that the former United defender is well placed to relate to players and potential new signings. Woodward believes that Ferdinand understands modern footballers and can sell the club's philosophy to potential signings or squad members. He could be handy, for example, in convincing Paul Pogba and De Gea -- both unsettled -- that United can match their ambition.
Another Ferguson pupil, Darren Fletcher, has also become a resource for Woodward. The pair remained in contact when Fletcher left United for West Brom in 2015 and the possibility of returning in some capacity once his playing career was over was always left on the table. Fletcher, who left Stoke at the end of the season, has not been handed an official role but has been offering help and advice in the first few weeks of the transfer window. Already well known to Solskjaer and Phelan, they are comfortable with his involvement, a crucial point in this precarious process.
The former Scotland international was one of those behind the pursuit of Dan James, confirmed as Man United's first summer signing on Wednesday, having seen the Wales winger up close playing for Swansea in the Championship. Fletcher has also recommended a closer look at 18-year-old Stoke defender Nathan Collins, his input fitting well with Solskjaer's preference for signing young, British players.
It is a subtle change but sources have told ESPN FC that the atmosphere in recruitment meetings is already calmer than a year ago, when Mourinho felt he was being pressured into agreeing to the signing of Fred by head performance recruitment analyst Mick Court. (The Brazilian midfielder hasn't lived up to expectations, a problem made more painful given the £52 million cost required to sign him.) Rubbing salt into the wound is the fact that the same recruitment team vetoed Mourinho's pursuit of a centre-back: United recorded one of their worst seasons defensively, going 13 games without a clean sheet and conceding 54 goals, a club record in the Premier League era.
De Ligt was discussed but head of global scouting Marcel Bout, who was brought to the club by Van Gaal, argued the Dutchman was too susceptible to weight gain because of his family history. The dissent came a year after Woodward and right-hand man Matt Judge were advised that Ivan Perisic, another Mourinho target, was only worth £22m rather than Inter Milan's valuation of £40m.
In the absence of a technical director, United will continue to buy and sell players in much the same way they did last summer and the one before that. The management team, headed by Solskjaer, and the recruitment team both have a veto, and agreed targets will be pursued, with Woodward and Judge taking over when the time comes to discuss a fee and a contract. Woodward and Solskjaer, in particular, face a critical eight weeks before the transfer deadline as they look to build a squad that can return to the Champions League quickly and in time to challenge for the Premier League title. For now, the responsibility lies with them.
Without a technical director to lighten the load, Woodward can only hope it goes better than last time.