The key to persuasion - in my small world of experience -is emotion. When someone is emotional they are ready neurologically to alter their mind.
When I wish to persuade someone ( face to face ) I try to spend time finding out what makes them tick. For some it is fear, others it is novelty, some like logical ideas but almost all respond to personal validation, non- judgemental empathy ( or sympathy if their is no common experience) and intensity.
As long as you can sidestep them associating your words or ideas with any flight or fight response you will be very persuasive.
So to get a hard core JW to contemplate a different idea you'd likely fail immediately with questions about the GB or 1914 but you'd get really far with discussions about yearning to be more moral / do more for Jehovah / show more love for family / get a clearer understanding etc. Once you are discussing a non threatening desire ( with a bit of passion) you can then share a deep 'fear' like - 'sometimes I worry that I'm too harsh on the local elders when I expect them to act spirit inspired all the time when sometimes they just make human mistakes and I'm certainly a very imperfect example myself. I just wish it was sometimes easier to see what J. was directing when he allowed <insert situation> to happen. '
Seeds planted (Elders not always spirit directed and sometimes J. allows uninspired stuff to happen.)