First though: some people are simply hard to talk to. They just don’t give you anything back. If you run into these people, don’t beat yourself up over it. Just give it a try and move on if you can’t get anywhere.
Now for the meat of my advice: ask questions. Always be asking questions. I find that people generally love to talk about stuff that’s close to them.
Let’s try just two examples:
1. Where are you from? - how big is it there? - do you live downtown or in the suburbs? - what’s traffic like? - what’s the weather like there? Hot summers? Cold winters? Much snow? Much rain? - is it expensive to live there? - much to do there? - do you do road trips from there? Is it close to other nice places? - etc, forever
2. What do you do? - What do you work on? Who do you work with? Hours? Keep up to date? Weekends? Evenings? How big is the company? How much time off? What do you do with your time off?
Basically I find myself constantly asking questions during these conversations. The more freely they talk, the more questions I’ll ask. I’ll also ask lots of personal questions later on in the conversation if things are going well.
How much is your house / car (generally) etc. The easy way to get to these answers is to offer your own: “The cost of living where I am is great, largely bc houses are relatively cheap. My house was $300k. I bet you can’t get a house for that much where you live?”
If you learn to start thinking in questions you’ll start to develop some good habits here and it’ll get easier.
But again, I can do this all day with the right people, but with the wrong people even 5 minutes I’d a slog.
Good luck!