Rioli is nearing the end of his ASADA ban, with an official return coming on August 20.
The 26-year-old has already been allowed to train with teammates from July 20, but the next deadline is set to open up debate with the Eagles' top brass.
Speaking on 3AW Sportsday, Simpson stated there are several factors in weighing up Rioli's immediate future, but revealed his delight to see the crafty forward's smooth re-amalgamation with his teammates.
"It depends where we're at", Simpson said.
"If we're in contention and playing finals and looking for our best side ... I think we've always said internally that we need to work through it with our leaders about where they sit with Willie [Rioli] and how connected they are with him and that's been really positive.
"He's done everything he can to work towards the redemption and it's been really pleasing and obviously he hasn't lost his talent.
"If that continues, I can't say how we can at least talk about it and see where we're at with it at all."
However, Simpson admitted it might be tough to find a spot for Rioli among other competing players at his position.
"In saying that all that, there's probably a player that has been playing in that spot all year so that discussion needs to be had as well.
"We haven't got to where we need to be, but we're on our way."
The Eagles currently occupy seventh place on the ladder, and will be hoping to add another four premiership points this weekend as they host fellow finals hopefuls St Kilda in Perth on Saturday.