How can established Stack Overflow users mentor new users to ask good questions?



I’m a Stack Overflow user, and for all its quirks, I quite like it. I’m a fairly experienced user over there, and I sometimes start, or participate in, conversations on the Meta site about how the site is run. I edit people’s posts every day for readability, grammar, spelling, etc. I am a frequent commenter, and will often explain to new users what a question needs to be (more) answerable.

There’s presently some conversations going on over on the Stack Overflow blog, and on the Meta site, about tone and inclusivity. As a white-cis-male-middle-class human, I tend to wave a bit of a “be nice” flag from time to time on the site, and I’m a big fan of hearing what people have to say about how amenable our community is to beginners and people who do not benefit from a full set of social privileges. Unfortunately, the current conversations on Meta are not particularly productive, and most of it is more of a left/right shouting match than anything insightful.

I do understand that Stack Overflow can be intimidating to new users, and I understand that better having read a heartfelt post from April Wensel just now (on Medium). Unfortunately Stack Overflow gets an enormous amount of free work requests, impossibly vague questions, and students wanting to cheat on their homework, and the quality systems have been designed to filter all that stuff out, quite justifiably. There are also quite a lot of unspoken guidelines based on netiquette and hacker culture, and for new folks, it must feel like tiptoeing around landmines and secret Masonic handshakes.

So, with that context set out, I was wondering if anyone here knows of any projects in which friendly Stack Overflow members, who know all the rules and guidelines, could mentor new users. I am all in favour of
alternative communities like Ask Questions (see also CodeNewbie) but I think trying to improve Stack Overflow is a worthwhile parallel task.


Here’s what I have in mind. It’s be a system in which users can post a question (publicly? privately?) that they’d like to post to Stack Overflow, and it would get helpful comments prior to the question author actually posting it. It’d have to be a community project for now, but it’s worth noting that something similar has been suggested to integrate into Stack Overflow itself.

Of course, such a system will not prevent a negative reaction when the question is posted, but I suspect it would help in a statistically significant number of cases. The mentor could conceivably add an encouraging comment under the question on the main site, which may also help ward off unduly negative reactions (I probably would discourage their upvoting the question though, as that might have the appearances of a organised voting ring).

Once a Stack Overflow beginner under mentorship has a bit of rep, and learned enough of the rules to get by, they could start posting on their own, leaving mentors with more capacity to focus on newer beginners.

While Stack Overflow may not have a great reputation amongst beginners, there are a lot of us who want to help folks who may not have had the easy ride we did when the site was younger. And, it should be said, of this self-identified subgroup, we’ll still sometimes be less welcoming of beginners than we should - communication is a thing that us humans are constantly learning, I think!


Feedback on this would be great. Also, how could we get started now? For example, could a new category be created on this very board?

If anyone wants to shoot general questions about Stack Overflow culture on this thread, and if it is regarded as on-topic by the site owners, be my guest. I’ll try to advise if I can.


Hi. :wave: Thanks for the question and being focused on finding solutions. Also, welcome!

I’ve been reading meta.SO for bit tonight and agree those conversations aren’t being productive, but I’d also add they are almost universally operating in the wrong paradigm(s). The community of speakers there doesn’t even have the vocabulary for the conversations needed let alone the will to have them.

I’d agree that trying to improve SO is a worthwhile parallel task, and I wish them all the luck in the world and send them wishes for success. But this site isn’t for beginners (in fact, most of us so far [anecdotally] here have 10+ years experience) and SO isn’t something you graduate to from here. This is a Q&A site to replace SO with something kind and inclusive. It’s also queer woman owned and operated and is informed by years of professional inclusivity work and unpaid activism. In reality, both sites will continue to operate in parallel, but in my dreamworld SO becomes obsolete like VCRs - a huge improvement on the past and a great thing in their heyday but still obsolete.

Also, SOs inclusiveness problems aren’t limited to beginners. That’s where a lot of the conversation about SOs problems happen because that’s a way easier conversation to have for privileged people than to address the underlying or more root issues - most of which come back to privileged people not doing the work to examine and adjust themselves. I honestly find there to be a level of victim-blaming in it.

The idea to get help crafting your question from someone who is part of the SO digital priesthood before posting to SO is not a new one. It’s a good band-aid solution, don’t get me wrong. Many people have offered this service on Twitter for months, if not years. If that’s where you have energy, I send positive thoughts your way for your endeavors. But that’s not something I want to be a part of. This is not a place for unpaid labor to help SO which is a for-profit company. For-profit companies need to pay people for diversity and inclusion work. is a place for us (kind people, under-represented people [and those two categories are a venndiagram, btw]) to help ourselves, for us to be empowered and to invest in doing it right from the start instead of paying the historical debt to get to something not as good as what we can make for ourselves.


Thanks, I appreciate your thoughts and explanations.

The point you make about volunteers propping up Stack Overflow is an interesting one, and it certainly does give me pause for thought - it is essentially what the userbase, including myself, are doing already :smile_cat:. I agree that Stack Overflow does seem to have something of a “monopoly mindshare” amongst techies, rather like GitHub, and proliferating a number of (kinder) alternatives would be a marvellous development.

Interestingly, since SO does not have much of a community deliberately, it may be that the userbase will break off and join other sites very easily. So, perhaps SO are worried that the inclusivity problems are getting worse, or that more people like April are speaking out, and new users will happily jump ship when kinder alternatives come along.

So, I don’t doubt new communities will form, and it’d be great if they do. However, I am conscious that Stack Overflow has cemented its position as a top tech Q&A site through a lot of arduous work that is going to be hard for unfunded volunteers to replicate:

  • Development work to build community and diamond moderation tools that work effectively (something that Reddit has struggled with a lot)
  • Getting the UI right, to shape the way in which questions and answers are presented cleanly, and in a way that maximises being able to find answers to problems from a search engine
  • Development work to build gamification and moderator election systems
  • Attracting enough inertia that people want to become volunteer moderators
  • The time required, in years, for a userbase of non-trivial size to form organically (especially in niche topics where smaller communities might struggle)
  • The time required for rules, guidelines and conventions to form, to get them wrong, and to put them right

I am conscious that my mental model of “what works” is probably informed by Stack Overflow because that’s what works for me. I’m aware too that the things I have assumed contribute to increasing quality (e.g. mutual editing, voting mechanisms, question closure) may not be welcome in a kinder environment. I am presently convinced that some questions just need to be stopped entering a platform, so that the community there does not get overrun with unanswerable questions and requests for free labour; simultaneously, I hold my hands up and say that getting this right from an inclusivity perspective (e.g. ESL) is a very hard problem indeed.

With that in mind, are there any public conversations about what kinder sites might look like? It may be that discussion forums are only the start - and I do like Discourse - but it would be fascinating to hear about a vision from folks who’ve been thinking about this for a long time.


@halfer, I don’t think you’re listening to me. I said:

TLDR: I said this ( is not a place for volunteer work for them (StackOverflow).

This is also not a place to argue that StackOverflow is the top tech Q&A site, that there are things about it that others might want to replicate, or to imply that because SO has been the only game in town for so long or that it has the network and branding effects of time that it is somehow better and therefore that’s where energy should be focused.

With that in mind, are there any public conversations about what kinder sites might look like?

  1. Plenty of folks have written about this. I trust you’re capable of finding them without asking URMs for free emotional labor.
  2. If you want an example, just read through this site. We’ve already done it.

I’m closing this thread now, because, again, this ( is not a place for volunteer work for them (StackOverflow).