David, I’m not too good at this but I remember hearing a story from the gemarah where (maybe) someone walked into the marketplace and asked eliyahu hanavi who, that was in the marketplace would be getting gan eden and he walked over to two people and pointed to them. later they asked them what they did that they would be zoche to olam haba and they said they made people laugh. I fixed a few details but I’ve heard the story several times, and the actual story is definitely true. I’m not overly learned so this is the probably the best I could do and I have no clue where you could find it but I’m sure if you dont know it then someone else on this board did because its probably very popular, because I never learned gemarah in my life. I apologize because I highly doubt this was the sort of source you were looking for. 🙂
one question, is your boss jewish? because I think it would make it very different if he is… 🙂