Free and Ginn finished first in their semi-final at the Shunyi rowing course on the outskirts of Beijing with a time of 6:34.29, ahead of the United States and Germany.
"It's always good to get them out of the way because it's the final hurdle on your way to the final," O'Brien said.
"You don't know what people are going to throw at you so you've really got to throw it out there and see what's going to happen.
"Fortunately today we threw it out there, it stuck, and they were able to take some good margin there early and as a result really able to control the race."
He said Free and Ginn have sent out a message to their opponents.
"They've beaten all the potential gold medal contenders already and I think most importantly they've got the mental wood on a few of those crews," he said.
"They've broken them, and broken through them in the last 400 metres on a number of occasions and I think that's very, very significant going into an Olympic final."
In other results, Australia's women's rowing eight progressed through to the Olympic final after a fourth-place finish in their semi-final.
The men's doubles sculls pairing of Scott Brennan and David Crawshay finished first in their semi-final to move through to the finals.
The men's four is also into the final after an impressive second-place finish in its semi-final.
Meanwhile Pippa Savage went out of the women's single sculls with a fifth-place finish in her semi-final.
Peter Hardcastle is also out after finishing sixth in the men's single scull semi-final.
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