My own approach: if I can afford the status-hit, I ask about stuff in a guess culture, and I explicitly answer questions there. In some cases I volunteer explicit explanations even when questions weren't asked, although I'm careful about this, because it can cause a status-hit for the person I'm talking to as well.
Some additional notes:
I was raised in two different guess cultures simultaneously, then transferred to an ask culture in my adolescence, and I'm fairly socially adept. This caused me to think explicitly about this stuff rather a lot, even before I had words for it. That said, I strongly suspect that there's much clearer understandings of this stuff available in research literature, and a good scholar would be invaluable if you were serious about this as a project.
Talking about "affording the status-hit" is oversimplifying to the point of being misleading, since I live in the intersection of multiple cultures and being seen in culture A as deliberately making a status-lowering move in culture B can be a status-raising move in A. Depending on how much I value A-status and B-status, "taking a hit" in B might not be a sacrifice at all. (Of course, being seen that way in A without actually making such a move in B... for example, pretending to my A friends that I am seen as a rebel in B while in fact being no such thing... is potentially a more valuable move, albeit a risky one. As well as a dishonest one, to the extent that that matters.)
The terms "ask culture" and "guess culture" are misleading as well; it's more precise to think in terms of topics for which a given culture takes an "ask" stance, and topics for which it takes a "guess" stance. It's even clearer to think in terms of preferred levels of directness and indirectness when trying to find something out, since successful people don't actually guess about topics for which their culture takes a "guess" stance, they investigate indirectly. But, having said all that, I'm willing to keep talking about "ask" and "guess" culture for convenience as long as we understand the limits of the labels.
A downside of asking for things in a guess culture is that people have to give you the things. (Unless you're demanding so much they'd rather refuse and lose you as an ally.) Imposing this cost on people hurts them, as well as lowers your status.
One of the lessons highlighted in the thread "Less Wrong NYC: Case Study of a Successful Rationalist Chapter" is Gender ratio matters.
There have recently been a number of articles addressing one social skills issue that might be affecting this, from the perspective of a geeky/sciencefiction community with similar attributes to LessWrong, and I want to link to these, not just so the people potentially causing problems get to read them, but also so everyone else knows the resource is there and has a name for the problem, which may facilitate wider discussion and make it easier for others to know when to point towards the resources those who would benefit by them.
However before I do, in the light of RedRobot's comment in the "Of Gender and Rationality" thread, I'd like to echo a sentiment from one of the articles, that people exhibiting this behaviour may be of any gender and may victimise upon any gender. And so, while it may be correlated with a particular gender, it is the behaviour that should be focused upon, and turning this thread into bashing of one gender (or defensiveness against perceived bashing) would be unhelpful.
Ok, disclaimers out of the way, here are the links:
Some of those raise deeper issues about rape culture and audience as enabler, but the TLDR summary is:
EDITED TO ADD:
Despite the way some of the links are framed as being addressed to creepers, this post is aimed at least as much at the community as a whole, intended to trigger a discussion on how the community should best go about handling such a problem once identified, with the TLDR being "set of restraints to place on someone who is burning the commons", rather that a complete description that guarantees that anyone who doesn't meet it isn't creepy. (Thank you to jsteinhardt for clearly verbalising the misinterpretation - for discussion see his reply to this post)