The centre-back has made 24 appearances across all competitions this season, predominantly playing alongside Leonardo Bonucci.
Though there has been some bumps in the road for De Ligt, his agent Raiola believes the 20-year-old's switch to Serie A has been a success.
However, he pointed out the absence of Chiellini, who suffered an anterior cruciate ligament injury in August, has not helped.
"It's a great balance. Virtually everything went exactly as we wanted, as we hoped," Raiola told Tuttosport.
"The only thing that didn't go so well is that Chiellini has been hurt. Having this great player next to him, Matthijs could learn even more and the insertion [into the team] could have been more gradual.
"But it is also true that sometimes if you do not dive into the water, you certainly cannot learn to swim, can you?"
De Ligt is not the only Juve player who has struggled to find their best form, with Maurizio Sarri's side embroiled in a tight title race with both Inter and Lazio.
They face Brescia at home on Sunday, with a win enough to - temporarily at least - take them above Inter into first place.