How to Give Bad News

Giving someone bad news is tough. Whether it’s a break up, a layoff, or telling my friend Todd I’m unable to repay the money he didn’t know I’d borrowed, everyone dreads those awkward conversations.

I read a story about a woman in China who faked her own kidnapping and death to avoid having to break up with her boyfriend. She had recently visited his family and hometown for the first time and learned he was poor, and decided creating an elaborate fake kidnapping and murder scheme would be easier than an awkward conversation. The police unraveled the scheme and I can only imagine the boyfriend’s shock, not only to discover his girlfriend had faked her own death, but also to learn women considered him a fake-your-death level of poor.

Many of us avoid awkward conversations and allow difficult situations to grow more and more unsatisfying. The secret to giving bad news is to avoid bad-news cues like “We need to talk” that will put the other party on notice to quickly excuse themselves to use the restroom and climb out the window, which is how I’m technically still going out with my 7th grade girlfriend.

Instead look for conversational keywords that will allow a seamless transition from casual chit-chat to “I think we should see other people and also I already am.”

For example, you’re a boss tasked with laying off workers and you notice Todd has recently lost weight:

“Wow, Todd, have you lost weight recently?”
“Yes I have. Thanks for noticing.”
“You must be down a whole size! Congratulations! While we’re on the topic of downsizing…”

Great job! You started with “downsizing” and worked backwards to find an opportunity to insert “down” and “size” into the conversation. Todd was never put on alert that bad news was coming.

Let’s try another one. You can go into a conversation hoping to recognize a keyword transition, but you could also plan ahead and find a broad topic like something that’s constantly in the news. For example, you want to break up with your boyfriend, and you worry he’ll be upset because damn!, just look at you, you’re quite the catch!

“Can you believe all these billionaires building rocket companies? Elon Musk, Jeff Bezos, Richard Branson have all the money in the world but all they want is space. Speaking of other things that need space…”

Great job! This new privatized space race is in the news every week. You might even be able to stretch the topic to multiple bad news situations like informing a child of the loss of a pet.

“Some people are actually volunteering to colonize Mars even though they know they might never return to earth. And you know who else doesn’t have much time left on earth? Bandit.”

I’ve made a list of some of the most common bad news situations and some ideas to get you started. First think of the common cliche phrases we use to give bad news and work backwards to connect them to common conversational topics you might encounter during the planned interaction.

Breaking Up with Someone
Potential keywords and common phrasing: wanting different things; going separate ways; going in different directions; splitting up; seeing other people; needing space; two roads diverging in a wood

Example: “Did you know the role of Annie was only cast after seeing 8,000 actresses? I guess the casting director realized when the chemistry isn’t right you have to keep seeing other people.”

Example: “Thanks to global warming the polar ice caps are splitting up. When will all the splitting up stop? First the Beatles, then the polar ice caps, now your Mom and I.”

Firing
Potential keywords and common phrasing: laying off; letting go; giving the sack; terminating; firing; dismissing; downsizing

Example: If a judge dismisses a case with prejudice it means it was probably an easy decision. It got me thinking about other things that would be easy to dismiss…

No Second Date
One awkward moment many people avoid is after a first or second date when there’s no interest in going out again. Instead of ending the date by saying, “This was fun. We should do this again some time,” when you have no real interest, be honest and try a transition.

Potential keywords & common phrasing: didn’t feel a connection; don’t see a future together; no chemistry

Example: I would take the subway home but there’s no connection. On the topic of things that have no connection…

Example: Global warming makes it hard to see the world having a future. Speaking of things I don’t see having a future…

I admit I don’t have the perfect transition for every occasion, and I’d be interested to hear if readers have suggestions for any of these common bad news situations:

Realizing you’ve served your guests expired food
Attending a party and flooding the only toilet
Gambling away your children’s college fund

And for that Chinese woman who faked her own kidnapping and murder, if she’d asked me for advice I would have suggested:

“I’m not interested in watching any sport that features poor sportsmanship. Speaking of poor things I can do without…”