This breed of people I know, think like I think, I have to present them with evidence they will think about, think, then digest, then research, then accept.
[Jews ... Israelites ... Hebrews ... Abraham...]
And as soon you diverge from their 'playbook', they'll mentally 'shut down' (except for the occasional JW who might already have their own doubts on the subject). JW literature casts doubt on any sources that disagree with their rather distorted views of history/archaeology/anthropology.
It's also problematic to present the historical development if at the same time you insist of sticking to the biblical story. There's no evidence Abraham (Jewish folklore) actually existed, no evidence of the Jewish 'Exodus' from Egypt (borrowed from Ethiopic stories), etc, much less the stories about Noah or Adam (borrowed from Babylonian stories).
With most JWs, the best response you'll get is, "well, that might be what the so-called 'experts' of 'the world' say, but I believe the Bible [by which they mean, JW interpretations]." You'd be much better off showing JWs a) issues with the organisation now, or b) how JW beliefs contradict scripture. (If the latter, discuss issues that are not overly subject to interpretation.)