Either right when they leave, and I need to see what work they had, or even months or years later, if we had a user who worked on something and we want to search for the request.
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Although you can't type their name in a filter or prompt, you can search for the deactivated user and grab their ID from the URL and use that. Once you paste the ID into the filter/prompt, just wait a second and select their name when it pops up.
Your use case would work great in an Assignment report, with an Assigned to ID prompt.