I have had GRADUAL success by using JW's own programming against them. All you have to do is undermine the "holier-than-thou" status that JWs feel about their religion by capitalising on their own religious bullying. First and fundamental step to deconstruction.
Always state your comments from a point of personal revelation, not a leading argument. For example, "I realise now that the Faithful and Discreet Slave is really just a group of men, trying their best. When you get down to it, you cannot base your faith on men's words..."
Discuss history of "false religion:" pagan backgrounds (holidays), failed teachings (sun revolves around earth/Gallileo), worldly involvement (support governments).
COMPARE: Are Witnesses completely free of this? DO NOT ANSWER THE QUESTION FOR THEM
(answers: celebration of Christmas, Cross, old light all after 1919 "cleansing", UN NGO status)
Discuss cults, what makes a cult? (JW will usually answer, "following one person.")
COMPARE: Where Witnesses ever like this? DO NOT ANSWER THE QUESTION FOR THEM
(answers: Russel, Rutherford were sole leaders and "FDS" of the time. Rutherford was "Judge", Russel was "Pastor", both lived in luxury, mandated doctrine, both accepted as used by God to this day.)
Discuss fringe religions (Mormons, Scientology). Weird claims (Mormons: golden tablets, holy underwear, lost tribe).
COMPARE: Did Witnesses ever make weird claims? DO NOT ANSWER THE QUESTION FOR THEM
(answers: Beth Sarim and return of "princes", failed dates, weird medical facts such as aluminum, vaccinations)