“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 hanging your family photo on the wall and someone asking if it came with the frame. 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: “Stephen, this is why no one likes you.”
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. Be careful with the “compliment sandwich.”
Instead of:
“Nice work pulling this together. Once we fix the messaging, the structure, and the tone, I think we’ll be in a good spot.”
Do this:
“Thanks for putting this together—I can see how much thought went into it. There’s strong potential here, especially in the core message. Let’s talk through how we can reshape the structure to make that message really land.”
The compliment sandwich isn’t inherently bad—it just tends to go wrong. When misused, it feels like being invited to a surprise party only to discover it’s an intervention. You showed up expecting cake, but instead you find your family quietly gathered around a circle of folding chairs, prepared statements in hand.
Misused sandwiches lift you up with generic praise, drop you into a vague yet crushing critique, and then try to soften the landing with some kind of cheerful parting phrase (“Again, nice work!”)—as if positivity alone could reverse the emotional trauma of what just happened.
But when done well—when the praise is sincere, the critique clear and helpful, and the tone genuine—it’s not a bad approach.
If you’re going to sandwich, sandwich responsibly.
And always remember that the praise should be more than a disposable wrapper around criticism. It should be just as nutritious, meaningful, and satisfying as the stuff in the middle.
2. Be specific—and tie it back to the goal.
Instead of:
“This is really interesting—curious where you were going with it.”
Do this:
“You’re onto something here. What if we reframed the opening around the customer’s actual pain point so we’re more likely to convert?”
Vague compliments are like gift cards with no amount listed. Technically a gift, but now it’s your problem to figure out what it’s worth.
Telling someone “This is interesting” can mean almost anything. Maybe you’re impressed. Maybe you’re horrified. Maybe you skimmed it on your phone between meetings and don’t want to commit to an actual opinion. Same with “cool,” “fun,” or “neat.” They sound polite, but they don’t help the other person understand what actually worked—or why.
A specific compliment tells someone: I see what you did, and it mattered.
Even better? Tie it to what we’re actually trying to achieve—whether that’s getting someone to click, convert, register, buy, or take action. It moves the feedback from personal opinion to shared outcome. Now it’s not just “I liked this.” It’s: “This is working. Let’s build on it.”
That’s not sugarcoating. That’s clarity. And clarity is always a gift. Even when it doesn’t come with a bow.
3. Ask questions instead of delivering verdicts.
Instead of:
“This part doesn’t really work.”
Do this:
“How could we make this part feel more relevant to the decision-maker we’re targeting?”
Telling someone their work “doesn’t work” is like handing them a puzzle, smacking away half the pieces, and walking out of the room. It’s blunt, it’s demoralizing, and worst of all—it’s lazy. You’re making them do all the emotional and creative labor of figuring out what went wrong and how to fix it.
But when you ask a question—especially one tied to the goal—you turn feedback into a conversation. You shift from “This failed” to “Let’s figure this out.” It gives the other person room to think, to participate, to be part of the solution rather than the problem.
Asking questions doesn’t mean avoiding critique. It means delivering it in a way that respects the other person’s intelligence and invites their input. It turns feedback from a judgment into a collaboration.
And yes, sometimes the answer to your question will be, “I have no idea.” That’s fine too. At least now you’re lost together.
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.
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.
