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When you have to deliver bad news, it’s not what you say, but how you say it. The worse the news, the more important for the recipient to feel that you truly understand them, you are there with them. Hence Clinton’s classic “I feel your pain,” i.e. “we are together in this dark, dark night”.

And you can’t just fake it–insincerity will often be felt instinctively. You’ve surely felt the difference between real and contrived smiles. You know it when you see it, but what is it that’s tipping you off? According to Paul Ekman, the leading expert on facial expressions, there is a clear, visible difference between a “social” smile and a “true” smile: in the former, the smile does not quite reach the eyes, or at least not in the same way. In a true smile, the inner corners of your eyebrows soften, and fall down. The reverse will be true for authentic sadness—true empathy—in which the inner corners of the eyebrows draw up, together.

Indeed, regardless of how well gifted actors and natural-born liars are able to control their facial expressions, they can only control so much: even when we control the main emotion showing on our face, the real emotion we’re feeling will often show up, albeit for a split second. These split-second “mini-expressions” are what other people pick up without even realizing it. It’s usually not enough for them to consciously realize what they’ve seen, but on a subconscious level, they know something’s off.

Hence, the obvious conclusion: no matter how many shortcuts you use, sincerity still matters. Once you realize sincerity is essential, how do you get yourself from here to there? The good news is that we have a natural tendency for empathy. One of the easiest, and most powerful ways to set this tendency in motion is to simply identify with the person, that is, “put yourself in the other person’s shoes.”
And when you do feel even the slightest bit of true concern, show it! Show your empathy in your facial expressions, your tone of voice, and then finally your words. Show that you fully understand not just how painful the news is, but all the unpleasant consequences it’ll bring.

If you share a true moment of empathy, it can end up forming between you an even stronger bond than before the bad news you had to give.