In my opinion, it's a good idea to ask "why?" or "what for?" when a stakeholder has an overly specific request. As you said, solving the user's problem is often even done best with a different solution (compared to what was originally requested).
Concerning your second point, Agile Manifesto co-author Robert C. Martin has a nice quote on this:
"I do big upfront design. I just don't believe in it." So I guess you are in good company 😁
I think you bring up some important points.
In my opinion, it's a good idea to ask "why?" or "what for?" when a stakeholder has an overly specific request. As you said, solving the user's problem is often even done best with a different solution (compared to what was originally requested).
Concerning your second point, Agile Manifesto co-author Robert C. Martin has a nice quote on this:
"I do big upfront design. I just don't believe in it." So I guess you are in good company 😁
I don't consider myself as doing big upfront design. But I appreciate the comparison. :)