It looks like someone who has been letting themselves be treated a bit too much like a doormat is going to start standing up for themselves today! You need to make sure you're there on the sidelines, cheering them on! This is a scary thing for them, and they can use some of your patented support to help them stand on their own two (wobbly) legs right now. Send along an inspirational email they can reference the next time they need a boost of self confidence.