Courtney won the 2010 V8 Supercars Championship with Jim Beam Racing, before signing a multi-million dollar deal to move to the factory Holden squad.
Skaife won three championships with the HRT, and drove alongside current driver Garth Tander in his final year with the team in 2008.
“James Courtney has his work cut out for him, in terms of coming into HRT and being able to exert enough authority in that team to get things serviced to him as he would like it,” Skaife told Speedcafe.com.au.
“The team is very much shaped around Garth and Garth's driving style.
“So that is something that will be hard for Courtney. Time will tell.
“It's hard to read the crystal ball on that one until you've seen him in the car and seen what the team looks like.”
Skaife believes that Courtney's level of success will depend on the team's ability to provide a car that is to his liking.
“It'll all be about effort and response from the team.
“Clearly they've got a very capable technical group – you've got to deliver that up to Courtney to give him a race winning car.
“Clearly he's a race winning driver, and if he isn't winning races then there'll be a reason, and it won't be because he had too much Christmas pudding.”
Looking to the rest of the grid, Skaife sees 2011 as a hard year to predict.
“It's very, very open,” he said.
“I think you'll see an improvement from the Kellys, and Jason Bright was strong at the end of last year.
“The changes with the factory teams will be the most interesting to watch.
“FPR were very strong in terms of speed at the end of last year, so it'll be fascinating to see how Will Davison gels with that team.“
The 2011 team and drive line-ups will hit the track for the first time today at Eastern Creek for the official pre-season test day.