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Misplaced Pages has a serious problem with helping new editors understand how to contribute constructively. We use jargon with them, we throw templates at them, and we sometimes lose patience with them. So here's my top ways to support somebody and give them feedback in a constructive way. The points below are mainly formed from my experiences at our #wikipedia-en-help IRC channel, but they probably also apply to the Teahouse and AfC Help desk.
We explain 'why'
It's really easy to tell somebody that they can't do something. But unless we explain why they can't cite it, we have no chance of actually making an editor understand. Take the time to write a sentence or two that explains what that rule is trying to achieve. People are much more likely to agree with a rule if they understand the intention behind it. Conversely, a badly explained rule can just feel like an insurmountable brick wall and leave the editor frustrated and confused.
But we don't explain too much
When we're in a position of experience talking to somebody newer, it can be easy to 'show off' how much we know. But more often than not, this simply confuses less experienced editors and overwhelms them. Stick to explaining what they need to know; not what we want to tell them.
We link as a last resort
When somebody wants to understand what a rule is, it can be really easy to just link them to the policy and say go read this. But most of our policy pages are completely incomprehensible, and (like the point above) tell the helpee way more than they actually need to know. Wherever possible, we should answer the helpee's question so we can be sure we explain only what they need to know, and in a way they understand.
We use plain English
By this, I don't just mean avoid Misplaced Pages jargon. We should match our speaking style to the person we are speaking to. If the way they write suggests that English isn't their first language, we're unlikely to be able to adequately explain a point if we throw around language more likely to be found in an 18th century dictionary. Simple Misplaced Pages has a really great guide on how to make your writing easier to understand.
Our tone matters
We might not realise it, but we usually say words in our heads as we read them. AND IF I WRITE LIKE THIS, you probably read them in a different tone of voice. We should avoid using caps lock for emphasis, and we should consider how ellipses (...) or exclamation marks (!) might change how our text is received.
And our language matters too
A lot of our conversations are around articles that don't meet our minimum notability criteria. I often see Your subject isn't notable. It's true, but it doesn't reflect that the person has spent time working on the article. Simply adding 'Unfortunately' to the beginning of the sentence to make it Unfortunately, your subject isn't notable changes the meaning of the sentence substantially. Our helpee now thinks we're on their side, and it suggests we recognise the work that they've put into it. For bonus points, we could talk about how they could try again in future once the individual has had more content written about them.
We assume good faith
We deal with lots of helpees who haven't managed to follow the rules around paid-contribution or conflict of interest disclosure, or have uploaded material that violates copyright. In almost all of these circumstances, our helpees aren't being malicious - they have simply failed to understand the vast amount of rules and policies that we have. As we do on-wiki, assume that a user is doing their best to contribute productively to Misplaced Pages until you have specific evidence that says differently.
Remember what we are representing
We are random people around the world hanging about in a chat channel (or on a WP page). But when we are helping somebody, we are the face of Misplaced Pages. If they have a bad experience with us, then they remember having a bad experience with Misplaced Pages. We are not professionals, and we are not right all the time, but the least we can do is keep calm and keep being polite. Particularly, remember that there are likely to be other helpees in the channel who can see what is being said while getting help themselves - we might think our words are appropriate in a specific situation, but an outsider might not see it that way.
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