He almost always starts by asking if someone grew up with both parents. That's an interesting thing to know but interview after interview this question leads interviewees down the same path and it leaves blind spots.
I hardly ever hear him ask in depth about their early experiences at schools, churches, childhood friends, extended family, the healthcare system, sports, media, etc.
There are some Freudian assumptions baked into his interview style and I think if he challenged himself to try other angles he could go from humanizing the guests to individualizing them.
To be fair, they're normally 30 minute interviews even in 3-hour long interviews very rarely do any interviewers go in depth on any subject. I think I understand what you want but I don't think you'll ever really find it.
He's interviewed drug addicts, gang members, prostitutes, gangsters, pimps, inbreds, cross-dressers, skinheads, rapists, homeless, transgenders, native americans, kids.
It lets me meet people I normally wouldn't have the patience to get to know, and it humanizes them.