What is a plan?
Everything seems to be in place at United, but it's just not clicking.
A working plan can be realizing that we needed better quality at left-back, right-wing & CB to play the kind of football we last season tried to, going out identifying good targets for those positions and getting them.
Signing Fred wasn't a bad thing, we needed more in our midfield and his profile seems to fit (hard-working capable at both doing the job defensively, playing through pressure and getting a through-ball), and if we are to trust Valencia then Dalot as a talented backup isn't a bad move either, but I think most our fanbase could havew said before the season ended that we needed a proper left-back and someone who makes us not fully reliable on playing through our left side in order to become so easy to defend against.
Our priorities should have been left-back and right-winger.
As for alternatives, in recent times these have moved (or have been said to be available):
LB: Mendy. (Sandro, Gaya, Tierney, Telles & Robertson, (with Rose being another option if we go away from hindsight)
CB: Laporte, Van Dijk & Bonucci (Alderweireld)
RB: Mahrez, Dembele, Costa & Silva (Pulisic)
And that's looking only at the ones who have moved or been rumored to move.
We've signed some good player, so it's not all doom and gloom, Matic, Pogba, Fred, Lukaku, Bailly, Lindelöf, Martial, Mkhitaryan & Sanchez might not all have worked out but were all signed to work in areas we were weak in. (except for Sanchez assuming now that he wasn't signed to be on the right)
I have been happy enough with our progress up until this window where I think we bought way too little and only on 1 semi-problem area as well as a rotation-alternative.
I expected us to at the very least on top of what we got sign one, preferably two more of the 3 problem-areas we have left, because in not too long we'll have to replace Matic in the first eleven, and we won't know if Pereira or McTominay will take the step to the quality needed to be a first choice player, and I'm now assuming that Dalot will naturally take over from Valencia.
That's just the last few years though, as for a plan under Woodward, there seems to have been none:
When he came into the position he said we can do what nobody else can do in the market. I'll excuse giving Moyes the job as it wasn't at least fully down to him.
LvG however was a disaster in every possible way, that same year Allegri moved to Juventus, Conte went to Chelsea, Pochettino went to Spurs, and a year after Klopp moved to Liverpool, Ancelotti went to Bayern. At the same time Emery certainly was available. Simeone might've been a stretch, but can't say it would have been impossible either.
Playing-styles we went to and from:
We went from Moyes who wanted to get it out to the wings to the theme of Benny Hill ran people crazy, again not something I put down to Woodward, but from him to LvG who was so scared of his own shadow that he wanted desperately to keep the ball at all times and not do anything that could get us a goal (we scored 49 goals during his last season) to Mourinho who has done a ok job at getting us higher up the table with results, but bores half our fanbase to death with reactive football instead of football that aims to entertain (mind, I'm not one of those who want Mourinho gone, but tons of our fanbase do want him gone because the style bores them).
We're all over the place, whether it's manager type or signings we've made pre-Mourinho. There is no certain plan to how we've wanted to make the team progress since Fergie called it quits. "Get in a renowned manager and give him some cash, if he doesn't do it for us then we'll fire him and hire another renowned manager and give him some cash" seems to be our plan, and it's certainly not one that will help us in the long-term, especially not if we are going to argue with the manager over a potential signings quality just because one of his earlier signings didn't live up to standards wanted.
For comparison in that aspect, Liverpool signed Karius during Klopps time, they didn't tell him no when he wanted to upgrade him with Alisson.
Same goes for when they signed Van Dijk after already having signed Klavan & Matip. No one is telling him he can't buy Keita or Fabinho because he purchased Grujic, Chamberlain or Wijnaldum.
City didn't stop backing Guardiola because Hart was replaced by the failure Bravo, and then wanted to replace him again with Ederson, and they certainly didn't stop signing player after player for ~30-50 million in positions he already had good players (Mendy, Walker, Danilo, Mahrez, Stones, Silva, Jesus, Gundogan etc).
Woodward & the board giving Mourinho a new contract just to half a year later not support him in the transfer-market isn't good planning. Back him or fire him. If they want a change of style then I'm sure a lot of people would understand that, but from Moyes to Van Gaal to Mourinho and then telling Mourinho that they decide the need of the squad suggests that style matters zip, zero & zilch and they are really only interested in minimising investment to stay as profitable as possible.