> After losing a few key personnel lately I have become painfully aware of the amount of knowledge stuck with individuals
Speaking as a technical writer who has worked deeply with engineering teams. You might be "missing the forest for the trees" here a bit by focusing on documentation technology rather than engineering culture. Your team doesn't feel compelled or rewarded to create documentation. Go to your head of engineering, CEO, etc., share the story of losing critical company knowledge when these people left, and suggest to them that the team needs to be properly incentivized to create docs. Make documentation a factor in promotion, bonuses, social recognition, etc.
The technology is more likely to take care of itself after that. Rather, you'll have more engagement from stakeholders and will have more confidence around what will work.
But beyond that, in terms of wrapping your head around information architecture, Divio's documentation system is a great start: https://documentation.divio.com/
You can hire or find technical writers to give brown bag lunches on documentation basics. I would do it for you. Poke around on my HN profile and you'll find how to contact me.
Last, I would set the expectation that it's OK to feel like you're winging the documentation. I suspect a lot of engineers don't write docs because they feel they are bad writers and don't know what they're doing. Just focus on creating a safe space to creating docs and keeping them up-to-date first. Over time as you all use each other's docs you will figure out why they suck.
The Write The Docs conference videos on YouTube are also an excellent resource.
What I mentioned in the parent comment is the top-down part of the strategy. The other side is the bottom-up leadership by example as mentioned elsewhere in this thread. Someone asks you for help, you point them to a doc and ask if they still have questions (and update the doc if they unsurface any gaps). If the doc doesn't exist you quickly create it and iterate.
Speaking as a technical writer who has worked deeply with engineering teams. You might be "missing the forest for the trees" here a bit by focusing on documentation technology rather than engineering culture. Your team doesn't feel compelled or rewarded to create documentation. Go to your head of engineering, CEO, etc., share the story of losing critical company knowledge when these people left, and suggest to them that the team needs to be properly incentivized to create docs. Make documentation a factor in promotion, bonuses, social recognition, etc.
The technology is more likely to take care of itself after that. Rather, you'll have more engagement from stakeholders and will have more confidence around what will work.
But beyond that, in terms of wrapping your head around information architecture, Divio's documentation system is a great start: https://documentation.divio.com/
You can hire or find technical writers to give brown bag lunches on documentation basics. I would do it for you. Poke around on my HN profile and you'll find how to contact me.
Last, I would set the expectation that it's OK to feel like you're winging the documentation. I suspect a lot of engineers don't write docs because they feel they are bad writers and don't know what they're doing. Just focus on creating a safe space to creating docs and keeping them up-to-date first. Over time as you all use each other's docs you will figure out why they suck.
The Write The Docs conference videos on YouTube are also an excellent resource.