David Moyes and Ed Woodward were facing the unknown at Manchester United in the summer of 2013.
Moyes had replaced Sir Alex Ferguson and Woodward had replaced David Gill, becoming the club's executive vice-chairman. It was a summer of transition. Those at the club were conscious of the importance of those months ahead of the new season, but that didn't translate into action in the transfer market as supporters were hoping for. United spent just under £30m that summer.
With transfer deadline day approaching that year, Guillermo Varela was the only player that United had signed.
His name might be equally as unknown now as it was then - Varela has still enjoyed a more than respectable career and currently plays for Dynamo Moscow - but it certainly should survive history in pub quizzes as Moyes' first United signing.
The full-back had impressed on a two-week trial period, but he was just raw potential. United needed proven talent. As the deadline began to loom closer, it was becoming clear that the club had failed in the market. The unknown was becoming bleaker.
Cristiano Ronaldo, Cesc Fabregas, Gareth Bale, Thiago Alcantara and Luka Modric were all linked to United that summer. Fabregas even held his own press conference to announce he was staying at Barcelona. It left the impression the player's camp had led United on a merry dance to get Fabregas better terms in Spain. Woodward would grow to expect those tactics in the years following.
After a summer of misplaced bets and a worrying lack of transfer activity, deadline day arrived and United finally made a signing, completing a late transfer for a midfielder that Moyes described as a 'top player'. It was Marouane Fellaini for £27.5m.
Fellaini was excellent for Everton, but it was impossible not to question the transfer. He didn't feel like a United player and he was perhaps unfairly tasked to overcome those pre-judgements before setting a foot on the Old Trafford pitch for the first time.
The window closed and it appeared Woodward had hopelessly failed at his first, most important assignment, however, only time could judge United's newest executive vice-chairman. It since has and it's confirmed what most concluded in September 2013.
That summer was a disaster for United and its consequences were vast. It could be argued they are still felt at the club today. United were at a crossroads and they turned in the wrong direction. They can't afford to make the same mistake this summer.
Woodward has now officially left United after 16 years at Old Trafford and Richard Arnold is the new kingmaker at the club. Arnold has been promoted to become the club's chief executive after spending nine years as United's group managing director.
It is thought that Arnold will not be involved in footballing decisions to the extent that Woodward was and that's probably for the best as United are at the crossroads again, almost a decade since Woodward and Moyes were facing that same unknown.
The season has been bitterly disappointing and United are in danger of being reduced to just trying to get Champions League football again. The wilderness years that followed Moyes are threatening to return, but there's also a more prosperous future in touching distance if the club can get major decisions right. That starts with appointing a manager and recruitment in the summer.
Woodward's first summer at the helm at United has set a low bar for Arnold's first summer to be considered successful. United want to sign a world-class midfielder and other signings are expected to be made. That already sounds better than just signing Fellaini.
It's the execution of those ideas that matter. With Manchester City, Liverpool and Chelsea all challenging for major honours, United have fallen behind - they have failed to build on last season's promise - and the club is currently delicately balanced.
The importance of finding the right manager to replace Ralf Rangnick can't be understated. It could shape the club's fortunes as it tries to avoid the failures of the last decade. Mauricio Pochettino seems a sensible candidate to have that responsibility.
There can be no more mistakes this summer in terms of the club's managerial appointment and recruitment.
The bar set by Woodward might be low, but Arnold will know the stakes have never been so high.
