Boss is very old-school: insists on paper files, hates cloud storage, etc. Technically not violating laws, but it makes secure organization impossible. How do I convince them tech aversion is the actual risk?

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Tell them it's quite literally illegal under GDPR (assuming it's applicable) to store sensitive files in an insecure paper format. Companies have been fined for it.

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Show them the fines, losing money always talks.

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