> Over the years I've concluded it must be because the way it's asked. People think there's something deeper in it than the most straightforward explanation. Or maybe they think they missed some critical detail and are afraid to ask.

I like your conclusion and I think it's something anyone involved with hiring practices should think about more.

I don't know if I'm the type of person a hedge fund would be looking for, but I would freeze on that question: My first thought would be, I wouldn't be willing to pay to play the game with "some guy" at all. But knowing that's probably not what you're getting at, instead I'm going to have to look for a solution to a problem I've never encountered.

But it goes deeper than that: If someone were to walk up to me and offer to play the game I just could say "No, thanks." and life goes on, a simple and low stress life decision. In a job interview I may be desperate, or at least hopeful, for the job; no thanks isn't going to cut it. You may not realize it, or intend it, but your warm up is asking how I face new challenges in life. No pressure.

Since the situation is new and hypothetical I've also got to consider the hypothetical details. These hypothetical details can branch widely and deeply, reaching into both the hypothetical world you've prompted and the reality that I'm being evaluated without knowing what you are looking for. E.g. Is it a loaded die? That would mean the question is loaded so, no that's a silly question; unless that's exactly the kind of thinking you're looking for, in which case it's an essential question.

Further, I know you already know the answer, and the trick if there is one, so the question might seem simple to you and you might not understand why I don't also just get it (which you admit). This means bad starts and bad questions can make me look bad which I definitely don't want (So, yes, I think there may be a critical detailed I missed, and I'm afraid to ask).

This probably isn't how you or other interviewers intend for candidates to respond to questions. One solution is for candidates to work on "interviewing skills" and get better at provided simple, canned answers. This makes sense if these interviewing skills part of the job but otherwise, in my opinion, distracts from exploring the candidate's talents and doesn't really give a good sense of company fit.

Alternatively, the interviewer could make their intentions and expectations clear for the candidate. For example, send the candidates your warm up questions a week in advance to let them prepare for the interview. When they get there ask them what they came up with and then probe them with deeper questions that get at what you really want to learn. Those who worked on your problems will be better prepared to talk about it.

I would like to see interviews try to draw out the skills the candidates possess and determine if they would benefit the company, rather then being a Company Exam. This might mean letting the candidate actually work with the team on a small problem, or just providing guidance and feedback to help them feel more comfortable talking with you rather than feeding you answers. For example, step them through the original dice game and then ask them to consider the variations.

EDIT: Fixed typos.