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I never even heard of Challenges. The overriding theme on SO meta seems to be the lack of staff engagement. Maybe you should focus on that instead?

If you have not participated in challenges yet, what might make you want to give it a try? I'm not going to participate in anything demanding a big investment in time. As a programmer, I really try ...

For users of sites other than Stack Overflow, could some version of challenges work on your site? Many sites could do writing prompts or writing challenges for native and non-native speakers. E.g. ...

For users of sites other than Stack Overflow, could some version of challenges work on your site? [...] What would make it successful, interesting, and fun? I really don't think you can make them '...

If you have participated in any challenges, which were your favorites and why? If you have not participated in challenges yet, what might make you want to give it a try? I haven't participated in any ...