When you have bad news to tell someone, just tell them. There’s no need to be cruel about it but also don’t keep them hanging: the sooner you tell them the sooner they can handle it.

I learnt that recently when there was a cockup over an event and I was sure I’d blown the whole thing. I put off talking to people about it for no reason other than the fact that until I did, the event was still notionally going ahead. And I wanted the event to go ahead. But eventually I had to do the deed – and within moments the reaction I got was completely okay. We won’t do that thing, we’ll do this instead. Sold.

I was relieved but also embarrassed that I hadn’t just got on with it.

Now I’m even more convinced because the Harvard Business Review says get on with it too:

Here’s what I’ve come to realize: 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.

But the more you do it, the easier and more natural it becomes. 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.

How to Start a Conversation You’re Dreading – Peter Bregman, Harvard Business Review (7 July 2014)

Actually, whenever something like this is done to me, when the person puts off telling me something, I am always put in mind of She’s on the Roof. Apparently it’s an old gag, but I heard it first – and I hear it again in my head every time this comes up – delivered by Sam Waterston in Capricorn One. Here’s a poorly done clip with an irritating watermark (it vanishes a minute in) of the scene in question. Waterson is one of three men being pursued by helicopters: