I'd call it an interviewer failure, not an interviewee failure.
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.
> when the moment calls for it
In an interview when you’ve been explicitly asked to discuss a topic to have a technical discussion about something is not when the moment calls for it. Doubly so if you’ve been asked twice. If you’re not willing to put aside being technically correct when you’re trying to show off your best self, it’s pretty likely that when things get tough, you’ll behave the same.
> unless of course what you’re being for is the willingness to roll over for unreasonable requests from people with more power
D, do you think that someone saying “can we please talk about a technical topic, here’s an example we’re both likely familiar with” is looking for yes men? I actively want my team and coworkers to challenge me, but I absolutely don’t want to work with that person who appears at every meeting with a list of reasons why we shouldn’t do X.
> I absolutely want people I hire to be "difficult" when the moment calls for it.
<3. What do you think makes the difference here in orgs that respect this and those that simply try to hire yesmen?