Thanks for this idea! I think this could be helpful for teaching newcomers to ask good questions -- I think one challenge would be if we could display good questions that have been asked to the mentor, so that the newcomer has good examples, instead of random ones. I'm not sure when we could think about this, though.

Pinging @RHo, @Trizek-WMF, @Tgr in case they want to post any ideas or comments.

In my experience the majority of questions is not helpful so given the limited space I wouldn't expect this to work well. It's also not an easy win technically - we store the list of questions in the asking user's preferences so we can pretend MediaWiki talk pages are a structured discussion system, but that leaves us with no easy way to look up other users' questions.

The way Q&A / support systems typically deal with duplicates is to 1) show you the most common questions or link to a FAQ, 2) show you similar questions after you have typed in your question. Unfortunately, MediaWiki talk pages not being a structured discussion system, I suspect there might not be an easy way to do the latter.

I agree this idea would be great but for the challenge that the questions shown should be helpful, and ideally relevant to the user. @Tgr's point about showing users similar questions after a user types their question reminded me we do still have this task T209327 open on the backlog. Perhaps we could group all these ideas into one tag on a future project to add structure to help so that we can implement such ideas (as well as enabling us to work on things like chatbots and improving help desks).

I think we a blocked by a bigger thing than our work: how messages are left on a user talk page. When you have a new message, you don't get that it is at the bottom of your talk page (how counter-intuitive!) and your talk page looks just like an article (how confusing!). Whatever we will built would be a temporary solution to a bigger issue. Tgr expressed it a different way, but the problem is here and persistant: our current hack is poor.

This said, anything that eases how newcomers can find back a conversation would indeed be helpful. Our goal is to keep the connexion between the mentor and the mentee live and strong. If the link is broken, it increases chances of newcomers giving up.

It's also not an easy win technically - we store the list of questions in the asking user's preferences so we can pretend MediaWiki talk pages are a structured discussion system, but that leaves us with no easy way to look up other users' questions.

I don't think this would be too terrible to implement to meet the basic use case: at the time when we save the user's question to the storage mechanism (a value in their preferences) we could also save some form of it to a long-persisted cache. Then when rendering the mentorship module we pull the content from the cache to display to the user. This could meet the proposal in this task description but wouldn't support the other desires for searchable content, surfacing most relevant, etc etc.

Yes, this thing would be very useful, especially considering that many mentors forget to ping newscomers. My only concern is that you want to hide the alert to the home page :)