OK, so it sounds like your boss is really struggling with his job, and this is cascading down the team. He's struggling to manage people, and he isn't able to support students effectively. He probably hasn't been given proper guidance about what his role is - he knows he has to have student interaction, but isn't really sure what positive student interaction is.
If you were in my HE institution, I know that there are specific training courses he should have gone on - I don't know that this is the case everywhere, though, and particularly not in FE.
I have to admit that occasionally I enjoy myself with ultra negative people by agreeing with everything they say, and then suggesting that it's even worse than they've previously described it. I can have a lot of fun like this.
However, I think it would be more mature and effective to tell your boss what you find helpful, e.g. 'X, I find it helpful if you tell me what you feel has gone well this month, so that I can make sure that I continue to do it. Can you tell me what went well?' Or 'So, you're saying that you think it's important that we support the students with their essay writing skills, and you'd like me to spend more time doing that.' And then sit there and write it down. And then next month, open up your notes and say to him 'last month we said we'd work on X, Y and Z, and so I have done A, B and C. What do you think went well about it?'