How will a machine ever replace his famous warmth or empathy?

Actually it shouldn't be too hard, just a cardboard cutout with a pullstring which, when pulled, intones "we're really sorry about this and it will never happen again, I promise".

They're going to be stuck in the uncanny valley where you feel like you can actually trust what the machine says.

That's why it's a hard problem, researchers are still working out how to properly get alignment with sociopathy.