Ray Wilkins says Andre Villas-Boas' biggest challenge as Chelsea manager will be to win over some of the high-profile names in the Stamford Bridge dressing room.
The 33-year-old Portuguese was appointed as Carlo Ancelotti's successor earlier this week, having left Porto following a trophy-laden season that included Europa League glory.
Villas-Boas previously worked for the Blues when Jose Mourinho was in charge, but Wilkins, who was Ancelotti's assistant until he was sacked last November, feels the new man will still need to prove himself to established stars such as John Terry, Frank Lampard and Didier Drogba.
Wilkins told BBC Five Live: "He is a young man who has done exceptionally well but it is a massive test coming in at Chelsea as they have big players and big personalities in there as well.
"Has he worked with players of the experience, quality and personality of some of the guys there at Stamford Bridge?
"It will be interesting to see how he handles it. If he can, and I believe he is a decent guy, I don't see him having a problem."
Former England midfielder Wilkins thinks previous experience of working under Mourinho will give Villas-Boas a base to build from in his own tenure as manager.
"His training drills will be organised, he has worked with Mourinho and the players were well into the Mourinho philosophy and he will know what the players require," he said.
"The bigger challenge will be when the games start and whether he can respond to the tactical situations he finds himself in.
"He knows what it's about from within the club and he will run the footballing side. It's a wonderful league because no two games are the same and I'm sure he'll enjoy that."
Wilkins also expressed his surprise that Guus Hiddink, who enjoyed a successful spell as Blues boss towards the end of the 2008-09 season, now appears unlikely to take up a director of football role at the club after initially being strongly linked with the managerial vacancy.
"I don't see that (Hiddink being appointed as director of football). They may do that from within the club structure. It's gone quiet on Guus but I think he would have been the perfect choice."
It has been reported that Hiddink's return to the club faltered because the Dutchman wanted to reappoint Wilkins to the back-room staff.