Oakley, who led the League as commission chairman and then chief executive for 10 years from 1986, told AFL.com.au that he was delighted when McLachlan was appointed the replacement for Andrew Demetriou.
"I'm thrilled Gill has got the job and I think he will make a terrific CEO of the AFL," he said.
"The most important thing for him is to enjoy it, otherwise there's no point in being there."
Oakley said a key requirement for McLachlan was to listen to those around him, but not to take everything he heard at face value.
"You have to be a good listener. I'm sure he will have his own views about things and that's fine, but he also has to be very careful to interpret what people are saying to him the right way."
As an example, Oakley talked about his first few months in charge of then VFL, which also marked the introduction of West Coast and the Brisbane Bears to the competition, amid widespread opposition from rusted-on and parochial Victorian supporters.
"If we had listened only to the fans at the time, we wouldn't have had Friday, Saturday and Sunday games and we wouldn't have had a national competition because the majority of people said they wouldn't keep going to the footy.
"But we had to press on regardless because the average supporter didn't understand we were in the entertainment industry and increasingly, people were seeking their entertainment at night," he said.
He added that most football fans were oblivious at the time to changes in the media and marketing landscape.
"What was happening around us was that TV networks were going national, and sponsors were no longer looking for state promotions. They wanted national campaigns so we had to offer them a national game."
Oakley, who has written a soon-to-be-released book about his time at the AFL, The Phoenix Rises, said he expected Demetriou to forge an excellent business career now that he had left the game.
"Today coming out of the AFL, you have a much better chance of getting back into the corporate world. In my day, once you became a football administrator it typecast you a little bit.
"I'm sure he will pick up a terrific job, but he has other business interests as well. He should be very satisfied with his time at the AFL and will get on with his life and enjoy it."
Oakley, who ran his own consultancy and sat on several boards after leaving the AFL, said he expected Demetriou would follow his own lead and stay out of the limelight.
"I've got a philosophy I've stayed with, which is, 'The king is dead, long live the king'. In other words, you're dead, shut up and let the next guy get on with it," he said.
"Go back through the records and you'll find I have said very little."
Twitter: @afl_hashbrowne
