Story provided by 99u – 

How should you start a conversation that you’ve been dreading? If you’re going to miss a deadline, do you ease into the bad news by first highlighting your project progress? Many people prefer to pad difficult conversations with fluff, in the hopes of dulling the inevitable impact.

On the other hand, Harvard Business Review contributor Peter Bregmen suggests that the most effective way for you to have uncomfortable conversations is to embrace the “cringe moment” and lead with the punchline:

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…Being direct and upfront does not mean being callous or unnecessarily harsh. In fact, it’s the opposite; done with care, being direct is far more considerate.

As long as your bad news is followed by a solution, you’ll be able to move the conversation quickly away from the mistake and back onto track.