For my taste, "Are you on track to meet the deadline?" is an intense discussion starter, as strong as a punch.
I think that depends entirely on _when_ the question is asked. If you get asked "Are you on track to meet the deadline" 50% of the way through the scheduled time then it should be a) An opportunity to reflect on your progress b) A chance to ask for help if needed Of course, if a shitty manager asks you that 3 hours before the deadline then ha ha ha good luck
But I find it to be of a totally different caliber than "Hey, what’s going on?" or "How are you? How is life outside of work?".
Vide asking "How was your last medical checkup?" in a personal conversation. Well, if it is good or OK-ish, it may be fine. In all other cases, it may turn a conversation into much more emotionally instense and sterssfull.