Well presumably this would be less of an issue if you had easy to use, easy to search and easy to maintain documentation, you know, maybe in the form of markdow

Well presumably this would be less of an issue if you had easy to use, easy to search and easy to maintain documentation, you know, maybe in the form of markdown files with a search bar where you could type 'how to paste image into documentation' in case you forgot... At the end of the day, if you've got someone who can't work out how to drag a file into a folder and then type  after you've shown them a couple of times, is this really the person you want writing the documentation for your process?