in reply to
Should a Socratic Dialogue be attempted?
I would suggest the application of a simple principle: don't play games with people. You can call this an application of the Golden Rule, if you like.
Also, I would make the point that we all have other things to do than hold someone's hand, trying to delicately lead them in a direction they don't (think they) want to go.
Once you understand what someone's problem is, it's eaisier to just explain the answer, or give them a documentation pointer.
On the other hand, there's no reason not to toss in some hints on how to figure things out along the way ("Did you try cutting and pasting that code snippet into a test script? I would think that if you'd had you would've
immediately noticed, that...").