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By tying it to the role - you make it possible to do with workflow. You'd have to get pretty creative with a script to do the custom record thing, but it's feasible. It would also require making it so that the users always had to run CSV import workflow/scripts and removing their ability to turn it off

<@UER9Q3SGM> you can turn off that option, right?  I think there is either a separate permission or just if they don't have permissions to scripts or workflows, yeah?  I seem to recall some people not having the ability to change that at some point in my last company.

Also - how do you add a checkbox to a role?  Or were you saying checkbox on the employee record?

You could also do it on employee record, but that would be painful...

Oh cool - don't think I've actually done that before

Yes - that option can be defaulted and your can remove the ability to turn it off or on