Not to burst any bubbles, but there are a few important things to consider.
Once this JW talks with the CO he will key her in on the possiblity that you are a dreaded apostate . He may be able to use simple fear inspiring techniques to whip her back into the flock (i.e. threats of disfelloshipping, reproof, ect.). It would be his job to put a stop to these sorts of things. Sometimes all a JW has to see is a person of authority not be scared or threatened by these sorts of things in order to feel that there is no problem. It's rather cheap and shallow, but sometimes the JW who is worried about their religion just wants to see some kind of conformation that everything is ok. A simple 'that guy doesn't know what they are talking about' may be all it takes.
It all depends upon where the person is.
And don't forget the fact that you are hiding the fact that you have been associated with the JWs. If she finds out about this while she is in the 'grey zone' she may feel quite betrayed and run back to the WTS. If you're going to draw her out without discussing your past it must remained sealed untill she can handle it.
I wish you the best.