How to find the perfect thing to say in every situation

Your colleague had a baby, and congratulations are in order! But wait - the delivery was very difficult, and there were complications. Now what do you say? Or maybe your boss is leaving your company and you want to strike the right balance of thoughtfulness, professionalism and humour in your farewell message. It's hard enough to know what to say in happy situations, let alone tricky ones. In almost any situation, a basic "Congrats!" or "I'm so sorry" follows etiquette rules and can suffice when the other person is just an acquaintance, but it often doesn't feel like enough - especially if you are close to the person or want to build a closer relationship with them.