I see quite a few questions like this one:
https://workplace.stackexchange.com/questions/27341/how-to-deal-with-requests-to-work-off-the-clock
(Please note: I'm not appealing this particular close decision; I'm raising a more general issue and using this question as an example.)
Questions like this don't quite fit the StackExchange mold because they describe a situation but don't ask a specific question. So, the question gets put on hold for being off-topic. In the example case, @jmort253 specifically explained what was needed, which is fine.
Here's the thing, though. In my experience people in situations like this often seek help partly because they don't know how to formulate their questions. They're in a workplace situation that doesn't smell right but they don't know exactly why.
There's a specific and well-known reason for that: Workplace issues are often iceberg issues. That is, they are 90% about stuff that's below the surface. In many cases, a good path to solving the problem is to have a non-confrontational conversation. But that's hard in situations with power imbalance.
In the example case the iceberg issue is "Boss, are you asking me to work without wages?". Even deeper and more significant are the questions "Did I do a bad job on this task? Did you have an expectation that I didn't meet? Are you going to fire me? Are you angry with me? "
Now, the rest of us have iceberg issues too. The question "are you asking me to work without wages?" immediately crashes into my personal "STOP! That's immoral and illegal!" iceberg. So, I might reflexively click "close: we don't do legal issues" on the question. But it isn't a legal issue (not yet, anyhow). Advising employees (how) to ask clarifying questions is definitely on-topic.
We could have left the question open. In that case, I might have advised the questioner: Say, "boss, please tell me more about what you expect from me on projects like this one. What do I need to do differently, if anything, to meet your expectations?" That question basically means "boss, where are your icebergs, and which one am I crashing into?"
To restate my question: Should we on Workplace close questions where questioners have a workplace problem but aren't quite sure how to reason about it -- how to navigate the icebergs? If we don't close those questions how can we best help those users? Useful answers about how to navigate the icebergs will help all our visitors, so they're worth keeping.