In this context, the question really boils down to “Do you want to ruin your former employee’s life to save a bit of company money?”. Which should not be a hard decision, but there’s way too many people who would disagree here. Kudos to the CEO to realize this and do the right thing, and good luck for your friend.
I think it’s more that most of these issues would never actually reach the CEO if brought up through standard channels. Some bs middle management explanation of why it’s not possible, even though they never passed it up. CEOs are still people, and if they just randomly receive an actual personal email that wasn’t debated over by a board meeting or considered inconsequential by people they hired to micromanage, they’re likely to just say fuck it why not.
