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Assume I request clarification in a comment on a question in the form of I see contradiction in the question in argument 1 and 2. Please edit!. Then, most users write a comment in reply without reading again their question (which is one of the most important and useful thing when editing). It is annoying if that happens (eventually multiple times) on an interesting, but yet contradictory, question (which is destined to be improved by comments).

Is it legitimate to announce that I'm going to downvote if the OP doesn't manage to edit and writes comment after comment leaving an incomplete or contradictory question and comment resolving that rather than a good question? Is is legitimate to do that after the 2nd, 3rd, ... comment and request to edit the question? Is it legitimate to do that with an OP who has x reputation?

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Yes, it is fine to comment before you downvote, even have a full conversation before you make up your mind.

I will often leave a comment suggesting fixes before casting a vote, it gives to OP chance to respond and fix their post. Some will respond and some won't, so pin the tab, give it 24 hours and come back.

Sometimes, it will be a user's response or lack of willing to improve the question so I can answer it, that will cause me to vote them down in the end, you can't imagine how many people say the question is perfect and I am just a troll or picking on them because I have more rep :/

Reputation is irreverent to how good someones content is, people make mistakes, the only difference is, higher rep users are more likely to fix an oversight fast, while new users will be unfamiliar with the format and may or may not take criticism well.

Of course, leaving these comments can cause users to react with hostility, so I understand why so many people just vote and move on but I feel, if one in ten new users adapt to the format and write quality posts based on feedback, it is worth the hostility you may face.

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    +1 nothing beats good communication on why things happen. – Jacob Vlijm Aug 3 '16 at 10:05
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    Why not downvote, and then explain the reason for the downvote? IMO, that's what downvotes are for, disagreeing with a post. If the OP edits the question/answer you can recast your vote by either removing your previous downvote, or change it to an upvote. Or keep it as downvote if you disagree with the post – Dan Aug 3 '16 at 13:07
  • @Dan Thats fine too but the question specifically asked about before voting, ie leaving a comment to say they will downvote this if it is not improved. You could do a whole other answer about doing it that way round if you like, it would still be relevant to the OP. – Mark Kirby Aug 3 '16 at 13:36
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    @Dan personally, I prefer first giving OP the opportunity to improve. Then upvote if he or she does, downvote if not. More encouriging imo. – Jacob Vlijm Aug 3 '16 at 13:38
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    @JacobVlijm that is definitely the best way to deal with new users, voting them down can make them just give up but also those downvotes can really hit hard on users with a good bit of rep :) – Mark Kirby Aug 3 '16 at 13:40
  • @Dan, downvotes on meta are for simple "I disagree with you" statements. Downvotes on main are for making a statement about the quality of a post, basically you are saying something negative about it. That's why excessive downvoting and also downvoting without giving any reason should be discouraged. – Andrea Lazzarotto Aug 13 '16 at 10:48

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