I have a job that requires me to talk to a range of different people. People think I am an extrovert, but I'm not. Talking with people effectively is a learned skill, and when you do it enough, it becomes a natural ability.
I'll say that I am not the most interesting or funniest person in any given room. I'm better at getting people to talk, rather than talking myself. I've had people say to me, "I just dished everything about myself to you and I don't know anything about you." Good! I like to collect stories.
Here are a few pointers if you like(I think most apply to both work and social situations):
Assume people are interesting. Because they are.
If you are in another's environment - home or work for example - look around for cues about what they are interested in and ask about them. This is the most effective icebreaker. I remember once asking about a couple's collection of crow art in a corner. It looked cool. It led to this great story of a pet crow they had.
Be enthusiastic about what you know others like, even if you aren't personally vested in that topic. Tell that woman with the sharp vintage style that her dress is fantastic. Ask the fly fisherman where he's been catching trout lately. You might find yourself learning about a fashion designer from another area or a gorgeous river. Go with that.
Ask follow up questions. Had a long conversation about concrete recently. He keeps saying, "I don't want to bore you..." and I'd throw in a question about concrete use or composition and the conversation keeps rolling. Concrete is mighty interesting, I'll tell you that.
I like to have the "hard" conversations with people. I'm not a, "Crazy weather, eh?" kind of gal. People will talk to you more about the hard side of life - about death or bad relationships or poor health or struggle - way more than you might think. And right there is where we are human. That's the good stuff. If you want to go down that road, you have to be non judgmental. Start with vague statements - "I heard about (this problem,) and I'm sorry you went through that." Some people will cut you off quickly, but many will give you an opening. They want to be asked by someone who wants to know.
Be that person. It's not as hard as you think.
And there are all the little things too - Don't look at your phone. Keep a comfortable level of eye contact. Lean in. Let natural pauses and silences happen in a conversation.
Those are a few things. I recently had a conversation about this with someone, and she said I was manipulating people. I disagree. I am aware of what I do that results in conversation. I don't think about it in the moment. The bottom line is you have to have a genuine attitude that the person in front of you is interesting. When you really believe that, all else falls into place.