“I can live for two months on a good compliment.”
Mark Twain
I used to work with a colleague—let’s call him Greg—whose skill in delivering compliments fell somewhere between a distracted parent praising their toddler’s abstract art and a doctor informing you that your condition is serious, but at least not contagious. Greg’s favorite phrase, always delivered with genuine surprise, was:
“This is actually not that bad.”
He’d say it brightly, eyebrows raised just enough to show how sincerely astonished he was by your minor competence. The effect was predictable and always entertaining (if you weren’t the intended recipient). You could literally watch someone’s soul leave their body as they processed Greg’s words: Actually? Not that bad? It was the sort of praise you’d reserve for airplane food, or maybe your neighbor’s kid’s clarinet recital—appreciation strictly relative to an already bleak expectation.
Yet even worse was Greg’s nuclear-level compliment—the phrase he reserved for only the most disappointing of successes:
“This is a good start.”
When Greg gave you a “good start,” you knew your work was doomed, a lost cause mistaken for finished brilliance. It felt like proudly baking a soufflé only to have someone gently inform you you’d actually made scrambled eggs. After a “good start,” your only option was to smile weakly, mutter something polite, and resign yourself to starting again from scratch—this time with properly deflated expectations.
All of this got me reflecting on other “compliments” I’ve received—those soft-edged criticisms disguised as encouragement. Why do we engage in this awkward dance of tepid praise? And why does a faint-hearted compliment sting more deeply than a direct insult ever could?
Let’s navigate the absurdity of lukewarm feedback together.
“Compliments” in the wild
Greg was certainly unique, but he wasn’t alone. The corporate world—and life in general—is filled with well-intentioned souls who manage to turn encouragement into existential doubt. Here are some gems I’ve collected over the years, each compliment delivered with the precision of someone firing blindly into a crowded room.
- “Wow, this turned out better than I expected.”
Translation: “I had absolutely no faith in you, but I guess miracles happen.” - “You’re surprisingly good at this!”
Translation: “I thought you’d fail spectacularly, yet here you are, firmly mediocre.” - “I can see how much effort you put into this.”
Translation: “Your results are suspect, but your desperate hustle is admirable.” - “No one can say you didn’t try.”
Translation: “I genuinely can’t compliment the result, so let’s applaud your stubbornness instead.” - “You know, you’re really improving.”
Translation: “Congratulations, you’ve finally achieved basic competence.” - “I’ve definitely seen worse.”
Translation: “While this isn’t a total disaster, it also isn’t remotely good.” - “This feels very… authentic.”
Translation: “Your work lacks skill and polish, but at least it’s honestly bad.” - “Interesting choice.”
Translation: “Not what I would’ve done, but then again, I value quality.” - “Stephen, this is why no one likes you.”
Translation: “Look, I’m just here to provide clarity.”
The truly fascinating part of receiving these pseudo-compliments is the mental gymnastics we perform afterward—twisting ourselves into knots, trying desperately to salvage a shred of genuine praise. It’s an Olympic sport for the insecure. (“She said ‘authentic.’ Authentic is good, right? Right?!”)
But before we delve too deeply into our neuroses, let’s pause for a moment and marvel at the sheer creativity it takes to craft such perfectly ambiguous praise—and it’s talent worth celebrating. Quietly. Privately. With a therapist nearby.
The science of the bad compliment
One might naturally wonder why anyone bothers with compliments that wound more deeply than honest criticism. Is it intentional sabotage? Passive aggression masquerading as helpful feedback? Or are we, as humans, simply spectacularly bad at direct confrontation?
From careful observation (read: a lifetime of awkward interactions), I’ve identified three core reasons behind our penchant for bad compliments:
1. Fear of confrontation
No one enjoys being the villain. It’s far easier to soften criticism by wrapping it in layers of vague positivity. Hence, “This is actually not that bad”—the conversational equivalent of hiding bitter medicine inside a slice of cheese. It doesn’t taste good, and everyone can still taste the medicine, but at least you tried.
2. Misguided positivity
Some folks genuinely believe they’re lifting your spirits, blissfully unaware of their own subtle cruelty. They think they’ve given you a gentle nudge forward, when in reality they’ve nudged you directly into a pit of self-doubt.
“You look tired, but like… a really professional kind of tired!”
Thanks, Janice. I didn’t even know that particular insecurity existed.
3. Lack of self-awareness
These complimenters truly don’t hear what they’re saying. They toss around phrases like, “You really pulled it together at the end!”—not realizing they’ve just implied you spent most of your time flailing hopelessly until the very last second.
And, in fairness, we’ve all been guilty of giving these compliments ourselves. I once told someone, “Your handwriting is very brave.” I still don’t know exactly what I meant, but I’m pretty sure it wasn’t entirely positive.
Perhaps the art of the bad compliment isn’t malicious at all. Maybe it’s simply human awkwardness, unfiltered and uncensored, stumbling around looking for something nice to say and landing somewhere between mildly inspiring and deeply insulting.
Whatever the cause, the bad compliment isn’t going anywhere soon—and frankly, I wouldn’t have it any other way. Life is complicated enough without everyone suddenly deciding to say exactly what they think.
How to give a compliment without wounding
At this point, you might be wondering, “Wait—have I been accidentally torturing people with my compliments all these years?”
The short answer is yes, probably.
But don’t feel too bad—we’ve all done it. (I’d like to once again apologize to Troy in HR, whose haircut I called “incredibly bold,” which, in retrospect, might have implied bravery rather than good taste.)
The good news is giving meaningful, genuinely helpful compliments isn’t complicated. It just requires intention, self-awareness, and occasionally, the ability to keep your mouth shut. Here’s a practical guide that, sadly, Greg never read:
1. Kill the “compliment sandwich.”
Instead of:
“Great job! Of course, it’s mostly wrong. But still, great job!”
Do this:
“I appreciate your hard work on this. Let’s talk about how we can align it even more closely with the project’s goal.”
The sandwich technique is well-intended, but so is giving children cough syrup that tastes like bubblegum. Everyone still knows it’s medicine. You’re not fooling anyone, and all you’re really doing is turning every interaction into an emotional roller coaster—briefly lifting someone’s spirits before plunging them directly into criticism-induced despair. Instead, just say what you mean—kindly, directly, and without the artificial sweetener.
2. Be specific—and tie it back to the goal.
Instead of:
“This is really interesting.”
Do this:
“The examples you used clarify complex ideas—exactly what we needed to reach beginners.”
Vague compliments—like vague criticism—leave too much to interpretation. “Interesting” could mean brilliant, or it could mean horrifyingly misguided, like when someone describes your carefully chosen new outfit as “fun.” (What does “fun” mean, Carol? What exactly is so fun about my shirt?) Specificity, especially when tied to clear goals, cuts through ambiguity and reassures people that your praise isn’t just politeness run amok.
And if you do need to offer criticism, frame it explicitly in the context of the goal:
“Adding clearer examples here would help beginners understand this concept.”
This keeps your feedback practical and objective, reducing the risk that anyone interprets it as a subtle commentary on their character, upbringing, or worth as a human being. It’s about goals, not souls.
3. Ask questions to guide improvement instead of criticizing directly.
Instead of:
“This part doesn’t really work.”
Do this:
“What could we adjust here to help this connect better with our audience?”
Nobody enjoys being told outright they’re wrong—even when they clearly are. Direct criticism can feel like you’ve been dragged onto a stage, given a bad haircut, and forced to accept compliments from strangers. Asking questions instead turns feedback into a cooperative mystery-solving adventure. It feels respectful, collaborative, and far less humiliating for everyone involved.
When all else fails, be human
And finally, when (not if, but when) you inevitably slip up, just own it. Admit your misstep with an honest laugh. Vulnerability, it turns out, heals wounds far quicker than awkward attempts at praise—or even well-intentioned cough syrup.
Conclusion: actually, this isn’t so bad after all
Compliments are strange beasts. They have the power to uplift, inspire, and motivate—or, if handled clumsily enough, to send us spiraling into the existential dread of self-doubt. (Thanks again, Greg.) Yet, as much as I’ve poked fun at the awkwardness of misguided praise, I have to admit I’m guilty of every misstep myself. The truth is, we’re all Greg sometimes, fumbling through our days and leaving a trail of unintentionally wounded egos behind us.
But that’s also why genuine, thoughtful compliments mean so much: because we know exactly how rare they are, and how tricky it can be to get them right. The good news is, despite all the misfires, the occasional bruised ego, and the mental gymnastics we go through parsing ambiguous feedback, we’re getting better. (And no, Greg, that’s not a veiled critique—this time I really mean it.)
In fact, if you’ve read this far, there’s hope for us both. We might even say to ourselves—with just the right amount of disbelief—“This is actually not that bad.”
And for once, we’ll mean it as the highest compliment.
