I love being deep in conversation with someone I care about. It's even better when there are a few people. As the number changes, the dynamics change. With each new person, you are adding not just them, but the relationship they have with each other member of the group. Context is what makes conversation juicy. When you have spent time with someone, you have a shared history. You know what makes them laugh. You know the areas to avoid. You know their treasure chests of knowledge. A lot of the virtue of being a good conversationalist, is just being someone who is good at understanding people.
Van Gogh's Potato Eaters in Conversation
The world of work can get in the way of this. Much of what we end up doing has to be self-promotional. If we just get on with a job in the background, we are relying on people to be aware of what we are doing. Unless you dig holes or fill them, the only person who knows how good a job you are doing may be you. If you are a real expert at something, you may be at the lonely edge where there is no one to talk to who understands you. There is a conflict here. Self-promotion sucks. It feels dirty. We also end up rewarding those who are overly self confident in a world that is so complicated that everyone should be confused most of the time. The person becomes more important than the idea. The person's identity gets wrapped up in ideas. Ideas should be stepping stones. Identities should be our connections to people.
Fortunately, most jobs have an end of day. A weekend. Once you have got through that awkward period where you transition from the work voice to home voice, you can breathe and start choosing how to be.
I am working my way through the curriculum of The Book of Life. The section on Aristotle has a wonderful bit on the contribution of conversation to the good life. In discussing things, Aristotle's Golden Mean of the right point being somewhere between two vices. In conversation you need to add sufficient humour to not be a boor, but not so much humour that you are a buffoon. You can't shoot everything people say down. You can't turn everything into a joke. You can find the balance which releases the good life.
'useless for any kind of social intercourse because he contributes nothing and takes offence at everything'
'cannot resist a joke, sparing neither himself nor anybody else, provided that he can raise a laugh and saying things that a man of taste would never dream of saying'