This also holds true for the more general case: be very very careful with jokes, especially sarcastic ones, whenever there is any kind of power differential. Th

This also holds true for the more general case: be very very careful with jokes, especially sarcastic ones, whenever there is any kind of power differential. The response really is very different than from an equal peer. Just think how these come across from a colleague or from your boss: "Who created this piece of crap? Haha!" "Well, I guess you will have to wake up earlier to finish it haha" "Calling it a day already today?" "Oh yeah this is pretty much the quality I expect from you haha" Humour can be a very powerful tool in a leader's toolbox but it takes a really really good relationship and a culture of emotional safety to work. When in doubt I'd always play it safe.