Hi Garrett, see what you can learn from my experience:
My best Witness friend ever - in my previous congregation - was my frequent partner in the ministry. For the first few years, he was an Elder. So when I started learning TTATT, I discussed and shared everything I was learning, and even gave him a copy of the letter which I'd sent to the Branch Office, which clearly showed a major teaching was false!
Over the next 4-5 years until recently, I never held back anything, and yet in all this time, he has never once challenged or tried to disprove anything I've told him. Why not?
Simply because he's terrified - terrified because he knows I've been studying & researching and he hasn't!
He's worried sick that if he starts digging, he's going to discover that his Org is no different from other religions in Christendom, (perhaps worse) and he'll lose everything he's "invested" by putting all his eggs in one basket. (case!)
"In denial" & cognitive dissonance" sums him up, sadly!