I tried to do A, and I really don't understand the response I got, X. Does this make sense?
I know it should be possible to do A, but I tried it and X happened. What sort of conditions would cause that?
I tried to do A, and X, Y, and Z happened. X makes sense, but I don't understand Y, what's going on here?
It doesn't really matter whether you're asking about automation or any other kind of testing. The tricky part is that before asking the question, you had better be pretty familiar with A, and you had better be able to report X, Y, and Z in a reasonable way.
I have a corollary, and I have a (counter) example.
I have seen any number of people in the software world complain about testers who submit bad bug reports. I'm sure it's true, I've seen the evidence, and it boggles my mind. A good bug report will explain A and explain X, and a great bug report will phrase the issue in terms of a question.
Not long ago I got an email from someone asking about a little script I wrote some time ago. He asked me to give it to him. I have not replied. I was astonished. For one thing, a cursory google search would turn up the 30 lines of code in question. But even worse than that: why don't you WRITE IT YOURSELF?
It's quite possible my script no longer works. It's quite possible that there are better ways to accomplish what the script does than what I wrote. But I absolutely refuse to copy'n'paste 30 lines of code in an email response.
Eric Raymond (if you don't know that name, google it) wrote an essay a long time ago How To Ask Questions The Smart Way. I'm guessing that many readers of my blog are not familiar with it. This is a travesty.
NB: the last time I pointed a software tester to Raymond's essay, I was accused of misanthropy and worse. Testing might be dead.