How I handle it? I don't know, it's kind of depends on what your inmate's like, honestly, and I'm pretty sure they've got different issues to handle.

Try to build up a rapport with him, I guess. Make sure he sees you as someone he can trust and who'll stick up for him if things go badly, but also make sure he knows you're not someone he can push around, either. It's kind of a difficult line to walk, but you'll figure out what works for you both.