I suggested some technical writing courses, but they got weird ideas from them, like writing documentation in a conversational style, which makes it somehow even worse...
I wrote documentation for a product earlier this year. A colleague with limited Python knowledge tried out the product using my documentation live, on a call. I learned so much from the process. We found bugs, we noticed that our documentation didn't have one clear usage path, which was confusing, and more.
Watching someone work through your documentation was a bit uncomfortable, but it really helped me. I plan to do it again with another documentation project on my hands.
Also, your colleague may need more direct feedback. I have picked up a lot of tips from the person who edits my work. Sometimes, I have an "aha" moment when I'm like "hm, this approach really is better!" and I take it with me in all that I write after that.
> writing documentation in a conversational style
The medium really matters. If the course was more about tutorials, a conversational style can be appropriate, if kept in check. If you are documenting open source software, it is different. Your colleague probably picked up good tips, but the course may not have shown how to use them properly.
I wholeheartedly agree with this. If you do this, especially with a user who is known for asking good questions, you will benefit greatly from it.
The most common form of bad documentation I come across is simply documentation with pieces missing: it uses terms without defining them, it tells you what problem an option is intended to solve but doesn't say what effect it actually has, and so on.
One possible cause is the "empathy" theory: the author missed that bit out because they assumed the reader already knew it. But I think it's more common that the author just did a half-way job, because we don't have a documentation culture that takes being complete and correct as the minimum baseline.
If that's the case, I think the advice authors need is to _not_ spend so much time thinking about what their reader is trying to do, and spend more time thinking "is what I've written complete?".
After reading this, I wrote a blog post. It will be part of the series, but probably released in a few days. I have so many ideas to cover! Now it's past midnight though, so I should probably get some sleep!
Thank you for the ideas!