00DAD,
I can't take all the credit for this but TotallyADD began asking if there had really ocurred a worldwide flood. So I offered to research it for him. When he was satisfied there was no evidence of such a global catastrophe, he started wondering what else might be wrong. This opened the door for me to show him the websites I had found, namely www.freeminds.org, JWN, jwfacts.com. By this time he was not afraid to read "apostate" literature. Having served as an elder for more than 25 years and having been raised a JW, he readily related to what Ray Franz wrote in "Crisis of Conscience". We followed up by reading "Combatting Cult Mind Control" and "Releasing the Bonds" by Steve Hassan. Two excellent books.
I think the most important thing is to listen closely to the concerns of the person you are trying to help. Ask leading questions a little at a time so the person sees for himself what a hokey religion the JWs is. When I visited a long time friend in the org she was spouting all the familiar catch phrases so I just left her alone. If she's happy with where she is, who am I to make an enemy of her by trying to change her? Although TotallyADD and I have left we are neither DF'd nor DA'd. I know that will make it more difficult for you to reach out to family members still in.
PATIENCE PATIENCE PATIENCE
Reopened Mind