Instruct him to install ovale and nerien's ovale scripts, and to use Catus to appropriately optimize his spec.
That would be fine for a casual/normal raider, but these guys are raiding HCs, if he can't do a rotation without looking at an addon for advice, he shouldn't be raiding that level. People who use these addons tend to tunnel vision them, and that is a hard habit to get out of. Catus would help him though.
To answer OP, he isn't applying rip/rake at the right times (I know he's not using RoRo), average bleed ticks of 90k is really low for his gear level, about what you get when you apply bleeds without any procs at all. I took that information from your dark shaman kill, I'm using RoRo but my average bleed tick was about 170k, which is almost double what his were. I would be expecting to see around 120-130k atleast with his gear. It seems he needs some sort of addon/weakaura (there's a really good one i posted in the feral pve guide on this forum, the one frag uses) which will tell him the strengh of the bleeds he is applying and make a much easier judgement as to whether he should clip a bleed or not.