It comes down to whether or not the person you're asking has the power to change things. If not then it's a fairly soul crushing question. Exponentially more when it comes from the same people that have not granted you the power to change things.
Like we were handed a solution to implement that architects and product folks had been talking about for most of this year. But they didn't include anyone that was day in day out hands on with the systems they wanted to change. To do that and then ask the people implementing if we can speed things up would be quite annoying.
It's asking them to contradict the design decisions that people 1-3 levels above them made. Risky business for sure. Even moreso for technical folks that in general aren't as adept at sussing out the difference between someone really asking and someone looking for a rubber stamp on a decision already made.