As one who only recently decided to leave, i can still easily remember the old life. Being born a witness, and staying till i was 26, the teachings and ways of a witness are still fresh. Please understand, you can not take a witness out of the religion by simply insisting they are wrong, or that their society is mis-leading them.
We are taught repiticiously NOT to dabble in other faiths or ideas, and to cut off those that act against these directions. We dont even question why we are taught that. Your only way of helping a JW is to find ones already questioning their faith, and then slowly build on their own dis-satisfaction. Let them lead themselves away. They cant be dragged away, or pushed.
Like in the Matrix, where Morpheus finds Neo because he was already searching for answers to questions. Questions he didn't even know yet. Neo just knew that something wasn't right, and was searching for what that was. Morpheus finds Neo, waits for the right time, and offers him the pills. It then becomes Neo's own responsability to see the answers or not.
God i love that movie.
PHIL.