Sometimes we wonder whether we should say something or not, probably because it’s sensitive in some way.
I’ve always reckoned that if we’re unsure whether to take a particular action or not, we should do the positive thing i.e. take the option that is active rather than passive. At least that way we’ll learn something even if the action doesn’t turn out that well, whereas if we don’t do anything, we’ll learn nothing. Over time that attitude has paid off, I would say.
If we’re unsure about speaking (or writing) to someone about something—if the decision is finely balanced, that is—we should go ahead, with the best skill and tact we can muster and if it seems the right time. At least then we move things on, even if the road is bumpy.
If in doubt, communicate.