1- If the setting is professional and nothing immodest occurs then yes it would be permissible.
2- Ayatollah Sistani states that any joking with the opposite gender is haram. If you are caught in a situation like that, be creative and find an appropriate balance. Don’t disrespect them, but at the same time avoid joking with them. If they naturally mention a joke, just handle it professionally by saying something kind and respectful, without carrying on with the joke and then giving your own joke.