I totally agree, and I think a lot of people will have been in this situation too. There is, unfortunately, no simple solution other than the very obvious one,

I totally agree, and I think a lot of people will have been in this situation too. There is, unfortunately, no simple solution other than the very obvious one, which is to use the right things for the right job, and as few of those things as you can. The really crushingly miserable situation is one where the documentation is in Confluence and Google Docs and some random files in Dropbox before they started using the first two and some files that someone shared on the Slack channel and a few things that are just in the CTO's inbox which he was sent by the CEO in PowerPoint and... it's utterly toxic. This proliferation of excellent tools we have today should be a good thing, but really we are all victims of our own best intentions sometimes (in that horrible chain of misery, even the CEO honestly thinks he's being helpful by emailing a PowerPoint rather than just telling someone over the phone).