I guess I got lucky!
I was flying with an owner and his son the other day, picking my way around the typical Southeastern afternoon thundershowers. Once we got clear of the worst of the weather, the owner looked at his son and said "You see, this is why we only hire pilots with a lot of experience". He has never questioned cost, and has never questioned my "Go, no go" decision. I guess I got lucky on that one!
Good luck with your boss. There are better ones out there!