“I can live for two months on a good compliment.”
Mark Twain
I once worked with a guy—let’s call him Greg—who gave compliments the way a cat brings you a dead bird. Technically a gift, but not one you wanted.
Greg’s signature move was the phrase, “This is actually not that bad.”
He said it with genuine surprise, as if he’d expected you to produce a wet napkin instead of a spreadsheet.
You could see people processing it—eyebrows furrowing, confidence draining, souls briefly leaving their bodies to file a formal complaint.
“Actually?”
“Not that bad?”
That’s not encouragement. That’s what you say about an airline sandwich.
But Greg had an even deadlier one in his arsenal. His nuclear compliment.
“This is a good start.”
If Greg said that to you, you might as well pack your things. A “good start” was professional hospice care for your ideas.
It got me thinking about all the “compliments” I’ve received in my life—the ones that make you question whether you’re being praised or politely dismantled.
Compliments in the wild
Greg wasn’t unique. The world is full of people who somehow manage to turn encouragement into an emotional pratfall.
A few of my favorites:
- “Wow, this turned out better than I expected.”
Translation: “I had zero faith in you, but I’m pleasantly confused.” - “You’re surprisingly good at this!”
Translation: “I thought this would be a train wreck. I was wrong-ish.” - “No one can say you didn’t try.”
Translation: “Your effort was inspiring. Your results were… interpretive.” - “This feels very authentic.”
Translation: “You made this with your heart, not your talent.” - “Interesting choice.”
Translation: “You have free will. You shouldn’t have used it here.”
And my personal favorite:
“Stephen, this is why no one likes you.”
No translation needed. That one’s just a family heirloom at this point.
The science of bad compliments
Why do we do this to each other? Why can’t we just say something nice and move on?
After decades of field research (read: living), I’ve concluded there are three main types of bad complimenters:
- The Conflict Avoider.
They can’t bear to say anything negative, so they bury criticism under a frosting of fake cheer.
“This is actually not that bad!” = emotional Pepto-Bismol. - The Over-Positive Optimist.
They think they’re helping.
“You look tired, but like… professionally tired.”
Thanks, Janice. I was just worrying my exhaustion wasn’t on brand. - The Oblivious.
They genuinely don’t hear how their words land.
“You really pulled it together at the end!”
Oh good—so I was drowning until five minutes ago.
We’ve all been each of these at some point. I once told someone, “Your handwriting is very brave.” I still wake up at night thinking about that one.
How to give a compliment without accidentally ruining someone’s week
- If you’re going to sandwich, sandwich responsibly.
Don’t use “Nice job” as bread for “This is broken.”
The goal isn’t to trick someone into eating feedback—it’s to make the meal worth finishing. - Be specific.
“This is interesting” is not a compliment. It’s an emotional shrug.
Try: “That opening line hooked me—I’d build the rest around that.”
That’s how you turn vague kindness into something useful. - Ask questions instead of dropping verdicts.
Instead of “This part doesn’t work,” try, “What were you hoping the reader would feel here?”
You shift from judgment to curiosity. And suddenly, you’re both on the same team.
When all else fails, be human
You will screw this up. You’ll call someone’s haircut bold and immediately want to move to another country.
When that happens, just laugh and own it. Vulnerability beats fake encouragement every time.
We don’t always get the words right. But the trying counts.
And if someone’s trying to tell you something kind—even if it comes out sideways—try to hear what they meant, not just what they said.
Because underneath every “good start” and “actually not that bad,” there’s a spark of someone who just wanted you to feel seen.
And honestly? That’s not a bad start at all.
