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It is clear that the main goal of flags is raising moderator attention to a possible issue and helping with the general clean up tasks. I was wondering how important is to educate new users as to how the StackExchange Q&A works.

As an example, lets say a new user posts an answer that should have definitively been a new question. Then the recommended actions (depending on your reputation) are to flag as "not an answer", downvote (if necessary) and / or vote for deletion.

Should I also comment the answer and let the user know that it should have been a new question instead of an answer? Should I comment in other cases where clarification could help the user understand what is wrong?

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    If you're flagging a post as NAA and even one reviewer agrees then an automatic comment will be posted by the system on the reviewer's behalf, so there's no need for you to comment as well in most cases.
    – Servy
    Nov 20, 2014 at 20:42

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I actually happen to have answered a very similar question on Startups Meta just the other day.

In essence, I'd say that, yes, if you're invested in improving the site and you have the will-power and desire to write a comment explaining the problem, then that's good practice. 99% of the time, unless it's a recurring problem, a moderator will not be so kind (logically so--when dealing with a hundred flags, it's difficult to stop and write something poetic for each and every one) as to leave a comment.

That said, no, it is certainly not necessary to comment. Assuming the flag warrants deletion of the post, your comment will likely be deleted as well. Sometimes I think it can be nice when you flag something as Very Low Quality, to leave a comment for reviewers to (try and--no guarantee) make sure they look specifically for what you saw, but don't trust moderators to see your comment. If your comment is necessary to validate the flag, use the "Other" option, or reconsider whether what you're flagging is truly in need of moderator attention.

In many cases where a comment and flag are necessary, the post will wind up in the "Very Low Quality Review Queue" anyway. If that's the case, it will likely receive template comments from various users there, and I generally just wait for those to come, rather than writing my own undoubtedly less concise or complete version of the same thing.

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If a user has done something wrong, then feel free to leave a comment on that answer. It's better if a comment left by either you or the moderator so that they're aware of why their answer got deleted, than if a comment isn't left at all.

That being said, leaving a comment and flagging a moderator serve different purposes. You flag a moderator so that they can come address the issue, and you leave a comment to help the user.

If you don't think that there's any value to you commenting on a post that you're flagging, than you don't have to. It's your prerogative.

And on the flip side, if you think that the issue will likely be resolved without a moderator's assistance, then you don't have to flag.

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