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
Well, it is an important question, when talking with a manager.
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.
I honestly think that is a reflection of the kind of management your company promotes.
In previous places I've worked, "are you on schedule?" would be an implicit attack - but in my current workplace checking in on people and making sure they're not silently struggling is a regular and casual thing.
Of course, if a shitty manager asks you that 3 hours before the deadline then ha ha ha good luck