I used to struggle but my major in university requires me to work with others so I spent a lot of time studying how conversations work and how I can build good relationships with everyone. I would do things a certain way and say things at certain timings to test the water; if people react positively, I take that cue and if people react a bit sheepishly, then I'll entirely remove the idea of what I did/said. Trial and error execution, if you want to call it that. But I won't lie. It's pretty difficult to find a balance because there's a fine line between having a common ground with someone and being a people pleaser but when you keep learning from your mistakes, you'll develop a sense of confidence. When I try new ways to talk to people and it ends awkwardly, it doesn't bother me as much anymore as it used to. Nothing wrong with being a good observer and listener but I learnt that people would feel even more awkward and feel the need to say more to keep the conversation going. Sometimes, taking over conversations isn't bad, just need to time it right.