When my husband confessed his doubts to me I was taken aback and it took a while for me to process what he was saying. I had my own doubts but had always held the thought that Jehovah would sort things out in his own time. However the fact I had doubts at all meat that I was probably willing to accept that the organisation was not always right. My husband was a bit relentless in taking every opportunity to diss the organisation and the early history and we would have conversations that got to the point when I had to say I've had enough today just stop.
He asked me to read Combatting cult mind control and at the end of the book I could accept that the organisation was at the least a high control group although I wasn't prepared to use the Cult word. I then read Crisis of Conscience and no longer thought that the GB were good men who made mistakes but corrupt men who didn't care about the flock and the religion was based on a lie.
It took time and my husband didn't necessarily use the best techniqies. Had I been an Uber dub then I may have confessed all to the elders early on. It worked for me but not for everyone. What I have learnt is that the person has to be ready to accept the possibility that the organisation is wrong. Unless there is something to build on it is very hard to engage them in conversation of any kind. It is usually a slow process and you need to progress at their pace. Letting them discover information for themselves can be better than telling them what to believe. Asking questions and asking for answers also helps.
Anyone trying to get family members out remember time is on your side there is no judgement day and imminent destruction and things change. Just because someone can't see your point of view today does not mean that they may not have doubts in future.