John Curtis has told Sports Mole that Ole Gunnar Solskjaer may find it harder to deal with owner Vincent Tan than managing Cardiff City in the Premier League.
The Chinese businessman recently clashed with Malky Mackay over transfer funds, which resulted in the Scot being sacked late last month, paving the way for Solskjaer's arrival at the Cardiff City Stadium from Norwegian side Molde in the process.
Solskjaer and Curtis played together at Manchester United and while he has little doubt regarding his former teammates's management capabilities, he has expressed concern over Tan's presence.
"It's going to be difficult for him working with that owner - Malky Mackay certainly couldn't. Having spoken to Ole and Richard Hartis, who used to be the goalkeeping coach at Manchester United and also worked with Ole at Molde, it was clear that he was using Molde as a stepping stone to get into the Premier League," he said.
"If you look at the betting odds of most jobs in the Premier League and Championship, he's always been in there. He wanted to be back in England working and Molde knew that, so that's credit to the relationship that he had with them.
"He's a great guy, a real gentleman and a thoroughbred professional. I hope that he can handle working with the owner and be successful. That's going to be key - managing up is going to be his biggest challenge rather than managing down.
"He lived and died football. His life evolved around the game and that's the kind of person that you need to be a manager. The role is all encompassing so it needs to be someone like Ole. Whether you thought he was going to be a manager, maybe not, but he's proved himself in Norway. This is a bigger challenge, where he will be tested every single week. My fingers are crossed for him. Henning Berg came back at Blackburn Rovers with people who were regarded as difficult owners. Whether or not he can be more successful, let's hope so."
It has been suggested that if Solskjaer made a success of his stint with the Welsh club, he could be in line for top job at Old Trafford in the future - something that Curtis believes is not beyond the realms of possibility.
"If he did well, absolutely [he could take charge of United]. They have always looked after former players. If he was successful, he's bound to get that opportunity at some point. He took everybody by surprise when he first arrived at Old Trafford. I remember when he first walked through the door, we all thought - 'who is this little kid?' Then he was banging in goals left, right and centre and went on to have a great career with the club," he added.
Solskjaer's first game in charge of the Bluebirds ended in a 2-1 FA Cup victory away at Newcastle United last weekend.