I have blown this one in every way possible. With that admission comes some degree of what works and what does not. I have to be able to say the right thing, the right way and most importantly at the right time to have a chance of being heard. This HBR post is excellent:
“Your boss proposes a new initiative you think won’t work. Your senior colleague outlines a project timeline you think is unrealistic. What do you say when you disagree with someone who has more power than you do? How do you decide whether it’s worth speaking up? And if you do, what exactly should you say?”