Since JWs are legends in their own minds and are coming from a place of ultimate authority, I think they think all they need to do for "encouragement" is say, "I know I'd sure love to see you there." In their minds there is never a reason to leave so the problem is you and so to them, "you know in your heart it's The Truth(tm)" so I think they get lazy when trying to encourage former members.
My aunt and uncle stopped by to see me a couple years ago and after an hour visit he said, "you know, Armageddon is still coming anytime now." Because he said that I know they counted their time for the whole hour.