It's a hard time for people like us to be in tech (particularly startups and small companies), because the culture of extreme passive aggressive is widespread and prevalent. Many people, most people, view direct requests as rudeness or condescension, even though the net result is exactly the same.
The worst part of it to me though, is that it can be hard sometimes to figure out what the person means. If they could just say what they mean, it would be so much easier. But no, instead we have to imply and hint our way to what we want lest we be taken as rude, and this requires the receiver to exercise some part of mind reading. Most of the time it actually works fine, but there are sometimes important and consequential moments when it doesn't work fine and there is miscommunication, sometimes with disastrous results. And completely unnecessary, if the person could have just said what they meant instead of trying to hint it. It doesn't need to be this way people.