My boss truly believes that keeping files on paper and locked in his drawer is the safest place ever. He is the type of guy that processes a file in Word/Excel, prints it, delete the file and store the physical paper in his drawer. Also, he deletes (not archive) all of his emails after reading them. If important, print it.
While I can relate to that sometimes, there are a lot of arguments to which this may not seem like a good idea. Especially if we need to access those pieces of information (as a team) daily, which means that if he is not in the office, we cannot access the information.
For further context, we scanned one of these documents once so we could keep a copy. He freaked out when he found out.
He is also a very technical person, exploring details, which needs to understand why/how.
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So, my question is:
How can I introduce my boss to computer file security, with file collaboration (or sharing) in mind, so he can maintain everything digitally but with a higher guarantee that it will not be stolen or anything?
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I once tried to explain that Google Drive/Dropbox is a good idea but I lack the technical arguments why.
He has a Windows 10 computer, a company mail hosted on Gmail with two-factor authentication, and his personal phone (Samsung Galaxy S8) with WhatsApp. All of the rest is on paper.
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He is also very methodical, so if there is a need to put passwords everywhere, he will do it. He is the type of guy that compromises User Experience for security.
Also, if there is a need for a local server, we can go for it as well.