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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.
Explain 'why'
It's really easy to tell somebody that they can't cite a primary source for an award that an article subject has won. But unless we explain why we 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 don't explain too much
When you're in a position of experience talking to somebody newer, it can be easy to 'show off' how much you 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 you want to tell them.
Use plain English
By this, I don't just mean avoid Misplaced Pages jargon. Match your speaking style to the person you are speaking to. If the way they write suggests that English isn't their first language, you're unlikely to be able to adequately explain a point if you 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.
Your tone matters
You might not realise it, but you probably say words in your head as you read them. AND IF I WRITE LIKE THIS, you probably read them in a different tone of voice. Avoid using caps lock for emphasis, and consider how ellipses (...) or exclamation marks (!) might change how your text is received.
And your 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.
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 you are representing
We are random people around the world hanging about in a chat channel (or on a WP page). But when you are helping somebody, you are the face of Misplaced Pages. If they have a bad experience with you, 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 watching what is going on.
Dealing with challenging helpees
If a helpee isn't getting the message, or is trying to troll, then it can be frustrating (and is usually the reason why people fail to 'keep calm'). Again, the most important thing you can do here is stay polite - it calms the situation, it shows other helpees that you have it under control, and it avoids giving some helpees the response they are looking for. If they persist, be increasingly firm in repeating your message - but always stay polite.
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