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You’re descriptions kind of make your coworkers like NPCs. If you want to have better conversations you should probably get to know them better as people. That can allow you to understand the why of their particulars and eventually guide your conversations more organically.
You don’t need to give explicit details of your coworkers’ lives, but from your writing it really seemed to me that you were more interested in mechanically optimizing conversation. This isn’t necessarily a bad perspective, but people already do that organically by understanding each other more and learning their history. The route of good conversation follows logically from there through empathy.