AshWills
You would probably get more benefit by asking questions that are more related to company culture, such as, how they're settling into the team, how they find the team morale/company culture, who in the team has provided them the most value so far. Those type of questions would hopefully help the new hire understand that you care about the culture at the company and also helps build a more personal relationship, which consequently will build trust between you and your employees to allow them to truthfully answer your initial question a few months later when they are more embedded into the team.
Definitely keep up the regular engagements with new hires though, despite not necessarily receiving the answers you're looking for.
Gary Vee Quote: "In very simple terms, “documenting” versus “creating” is what The Real World and the Kardashians is to Star Wars and Friends. And don’t get confused—just because you’re “documenting” doesn’t mean you’re not creating content. It’s just a version of creating that is predicated more on practicality instead of having to think of stories or fantasy—something that’s very hard for most people (including myself)." - https://www.garyvaynerchuk.com/creating-content-that-builds-...
Gary himself may work long hours on minimum sleep but he has always said he is wired differently to many people and that sort of lifestyle isn't sustainable for most.
However, I do agree that the list is interesting, there's some good content I haven't come across before which is always nice to find; thanks OP!