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My suggestion is that when someone is asking a question, certain conditions cause a message to appear advising the user that their question may be appropriate for community wiki status, and explaining briefly what this means. The conditions under which this would happen would include:

  1. The title containing any of the keywords:

    • favorite
    • opinion
    • most
    • least
    • best (or possibly phrase "are the best")
    • worst
    • think
    • feel
  2. Any of these tags are used:

    • fun
    • subjective
    • not-programming-related (for SO)
    • poll
    • off-topic
    • humor
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a form of this already exists. Go to the /ask page and try entering some of these keywords in the title, then press tab. – Jeff Atwood Jul 4 '09 at 13:30

The rules for what is Community Wiki are so screwed up already I don't know if you could effectively program to look for questions that might be CW status.

I think before we try and provide helpful tips to question askers, we need to figure out what CW actually means first.

It should also be noted that they could easily avoid the little warning by just not using those tags as well.

share|improve this answer

I like this suggestion, but would also like to see them start out closed and require five votes to re-open...

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You're a damned dirty fascist. – TheTXI Jul 2 '09 at 17:38
Pony-loving hippie! – Shog9 Jul 2 '09 at 17:41
MALE LOVE NOT WAR! – TheTXI Jul 2 '09 at 17:44
Uh...nice typo? – Thomas Owens Jul 2 '09 at 17:50
... Well his image is of a Pony. – Brad Gilbert Jul 2 '09 at 19:44

Let's just start everything as CW and require 5 votes to turn it into a regular question. I'm only half-kidding.

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I actually think it should take 25 votes. – Hilarious Comedy Pesto Jul 2 '09 at 17:46

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