1. Look inward.
Even before you pick up the phone or meet with the person, start by getting yourself into the right mindset. "Find compassion in your heart for this human being beforehand," say the Chernoffs. Consider how you'd feel if you were them since speaking from a place of empathy can affect the tone of your voice, making it gentler.

2. Be calm and clear.
As you well know, but it bears repeating: Now is not the time to be funny or indirect, despite the fact that in many difficult situations, humor can be a godsend. Here, you want to be as to the point as you can, and give the news directly.

3. Prepare for the reaction.
Know that the reaction you're going to receive is nothing personal, the Chernoffs note. The person may respond with anger or become accusatory. "Really bad news can take almost everything away from a person, for at least a few moments." So don't take the person's reaction to heart; if you can drop any expectations of how you think they "should" respond, you'll actually be able to make yourself available to help them in a sympathetic way—because you won't be hung up on how you think the situation should be playing out.

4. Put it all out there.
When delivering the news, it's always important to be actively aware of how the person you're speaking to is absorbing the information, and this is especially true for bad news of the multiple-layer variety. If the person begins to spiral into a panic attack after you tell them the first part, the Chernoffs suggest trying to be present with them—listening, taking in their reaction, sitting with them, until they find composure. But don't withhold the rest of the news for another time—this only makes matters worse, because "a person can't cope effectively if they've only been given half the story," say the Chernoffs.

5. Resist the urge to give advice.
While it's easy to lean on positive phrases to temper the situation, such as "It will be okay," "It's not that big of a deal," "You just need some fresh air" or "It's time to move on," these words often come across the wrong way—thoughtless, empty and essentially worthless—despite your best intentions. In fact, the Chernoffs say it can exacerbate the impact of receiving bad news. They also recommend to not pretend that you perfectly understand what it's like to be in the other person's position. "We all internalize pain in different ways," the Chernoffs say. So what might seem like logical advice or reassurance to you won't in most cases immediately make sense to the person on the receiving end. Sometimes life and pain defy logic, especially in delicate personal situations. For now, just give the news—and know that you've done so in the most humane way possible.

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