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So, just because a chat is deleted by a user does not mean it is deleted from the system. IT should be able to pull it back up if necessary. Nothing truly is deleted in the digital age...
This is the argument I would go back to the owner with. Let them know most deleted chats are either to correct an error or no longer needed however, IT should be able to pull data... if that's how you want them to spend their time/resources ($$)
Pro
Tell them “no.”
Report back as to how that works.
Otherwise, do as the owner says unless it is illegal. That is how you stay employed.
Chief
This is why I will never again work for an owner/founding CEO. The vast majority know literally nothing about being a good leader. The only great leader I ever worked for had experience in HR so knew how to treat her people, and her company wins "best place to work" awards in my region from multiple publications -- and those awards are earned because we employees complete the surveys asking us questions about working there.
Senior HR bp
I'd start by asking what the reasons are behind such a decision. Then find a way to tackle the issue (trust issue?) in another way.
Chief
That would definitely raise questions for me too. Any policy around monitoring communications needs to be very clear about the purpose, expectations, and privacy implications.
And, if you have any employees outside the US, tons of regulations re: transparency of how data is stored and used. Monitoring is fine if it’s disclosed to employees and handled correctly.