I absolutely want people I hire to be "difficult" when the moment calls for it. If the scenario is one where the right business/user choice is "let them keep using Google Sheets", then the answer I want is "Google Sheets seems fine to me", no matter what people with more power start out wanting. Too many developers have been encouraged to be minions, not professionals.
Ditto for ones who act like everything is a nail for their coding hammer. A developer who can save a company a couple hundred thousand dollars by not turning something simple into a big coding project is a rare and precious commodity. Or should be, at least.
The thing to do isn't to give demerits for "being difficult". The thing to do is to then add something to the scenario where they get into the thing you want them to get to. "For this, we need better access control than Google Sheets allows us." Or, "We need this to be more closely integrated with our accounting system."
Unless, of course, what you're hiring for is the willingness to roll over for unreasonable requests from people with more power. Which, honestly, a lot of places are.
