A good piece from the Harvard Business Review on jumping into difficult conversations. I agree wholeheartedly with the idea that you just have to jump in at the deep end sometimes.
“I almost always overestimate how difficult it is for the other person to hear what I have to say. People are resilient. I’m usually more uncomfortable delivering a difficult message than the other person is receiving it.Next time you have a conversation you’re dreading, lead with the part you’re dreading. Get to the conclusion in the first sentence. Cringe fast and cringe early. It’s a simple move that few of us make consistently because it requires emotional courage. At least the first time.”