Help me ask why you didn't just

My go to for this is to say "I'm guessing $solution didn't work." Because then you're supposing a solution that most likely the other person did already, and you're communicating that you'd assume they'd already thought of it, and in the odd event that they didn't, they can just say "Oh, I guess I didn't think of that."

That said, whenever I walk into a scenario where someone's been plugging away at a problem for a good length of time, especially when it's someone I trust and know to be competent, almost invariably the answer is yes, they did try it, but asking in this way often then illicit the person to explain what went wrong. And after a few rounds of it we've eliminated a number of the more obvious solutions that didn't work, and I'm now up to pace and can try and provide better ones.

> And honestly I think phrasing isn't that important - if you know someone for months or years and aren't usually a dick - people won't automatically assume the worst.

I'm actually quite surprised that you're the first person I've seen mention this, because in my personal experience this is exactly the answer. People seem to receive that question well regardless of it's form when it comes from someone that is known to be relatively open and non-judgemental.

> My go-to heuristic is "the wordier the question, the more likely it is to be perceived as well intentioned."

Just wanted you to know that I have a conflicting heuristic (which admittedly may or may not be unique to me): "the wordier the question, the more likely it is that the intention is being hidden from me".

Inefficient, wishy-washy, wandering questions set off my spidey sense that tells me I'm not getting the full picture. Earlier in my career, such an interaction would have left me with some risidual anxiety, feeling unsure that I'd been given honest feedback and questioning whether I'd done a good job.

I'm speaking only from the point of view of a review situation of course.

Have you tried "Have you tried x?"?

This follows naturally from "What have you tried?", from the "information to include when asking for help", on which Q&A sites seem to agree.

It's rather innocent at face value and it leaves the door wide open for the person to explain what went wrong when they tried, or why they opted against it without trying, etc., without implying anything negative --except to a really frustrated and/or rough-edged person who is determined to receive everything in a negative way.

Yes there are a dozen mentions already for "did you try/have you tried" so here's my grain of sand on that pile.

For me, one question like this isn't too bad. Ten are. Then it becomes a botched kind of Socratic dialog. In a true Socratic dialog, the teacher (who presumably knows best) controls the flow of explanations. In "why not just" the learner wrests that control away while still expecting the teacher to do all the work. It forces the explanation to take the form of an (unsought) argument. I have several friends who routinely use this method to learn a new area. One of them does it so consistently and aggressively, even after I've called him on it, that he's now an ex-friend.

The killer combo IMO is "just" (setting up a default position) and "you" (associating an initially assumed-inferior position with a person). That's why phrasings like "why doesn't ssh work here" aren't as bad. They keep things collaborative rather than adversarial. This becomes particularly clear with repetition, with a series of "why don't you just" bearing a stark resemblance to a legal cross-examination. It's better to avoid those two markers unless you know that's what both parties are after (which is fine when it happens BTW).