This is going to sound ridiculous, but I LOVE backhanded compliments.
In fact, I consider myself a bit of a connoisseur. The very best ones require the perfect combination of wit, sincerity, and disdain to create a good piece of bittersweet praise. There is an art to giving a good compliment and it takes a special twist to make it a perfect backhanded compliment.
Some of my favorite backhanded compliments
To deliver a truly stinging backhanded compliment you need to know someone really well. They have to accept the superficial, true part of the compliment and recognize the stinging subtext. My ex-girlfriends were especially good at them.
So when I got this backhanded compliment in my comment section a while back, l was floored:
Pure art. I’m still smiling about it now.
I actually held a little contest for my readers after I read that “compliment”: What’s the BEST backhanded compliment you can give me? I asked them to put their answers in the comment section…
…and the results were HILARIOUS.
Here are a few of the best ones:
Ouch. Solid burn, Sheridan.
Ha! I bet he’d change his mind if he saw the site now.
Subtle…yet oh so effective.
So today I’m going to tell you how to deliver a cutting backhanded compliment. But first, that requires a knowledge of the fundamentals. You can’t run before you jog, people.
So we have to start with what makes a “normal” sincere compliment work or fall flat.
How NOT to give a compliment
Many people have a misconception that giving a compliment is as easy as saying:
- “Nice watch.”
- “I like your dress.”
- “Cool car.”
…when this simply isn’t the case.
I don’t blame them, though — even I’ve been guilty of thinking this before.
It takes a lot of practice and a lot of screwing up before you learn that compliments like these are incredibly shallow — and when you give them, people can sense their vapidness and you just come across as insincere.
In his book How to Win Friends and Influence People, Dale Carnegie put it best:
“The difference between appreciation and flattery? That is simple. One is sincere and the other insincere. One comes from the heart out; the other from the teeth out. One is unselfish; the other selfish. One is universally admired; the other universally condemned.”
People aren’t stupid. They know a weak compliment (or “flattery” as Carnegie called it) when they hear it. They also know the value of a good authentic compliment and appreciate it.
I want you to think back to the last time you got a compliment that really made you smile. When was it?
Was it someone at work saying you did a great job at a presentation? Was it from a friend who you helped move?
Think about that compliment. Chances are, it was thoughtful, authentic, and it made you feel great.
A sincere compliment — like its backhanded cousin — is an art form. Once perfected, it can open the doors to a world of new relationships and connections that would not have otherwise happened.
The question then is “how?” How do you give a good compliment that’ll come across as sincere and meaningful?
The art of observational compliments
The observational compliment goes a step beyond “Nice dress” or “I like your tie” and shows the person you’re complimenting that they have EARNED your appreciation.
Bad compliment: “You’re the bravest and smartest person I’ve ever met. Teach me your ways!”
Observational compliment: “You know, you seem pretty adventurous. I know a lot of management consultants, but I don’t think any of them would go skydiving in their off time. That’s pretty cool.”
See the difference? On top of being weird and kind of creepy, the first one isn’t authentic and people will pick up on that.
The second one is much better — and it works for two reasons:
- People LOVE to hear about themselves. This is the reason things like the Myers-Briggs test and astrology are so popular.
- It shows that you’re LISTENING. People love to feel heard, and when you’re able to showcase that you were paying attention to what they were saying, they’re going to respond well to your compliment.
Giving a good compliment is actually pretty simple — though hard to master. All it takes is 3 easy steps.
Step 1: Ask thought-provoking questions and LISTEN
Like so many of our issues, the problem of how to give a good compliment starts with simple listening. When you’re speaking to someone, spend about 5 minutes building a solid foundation of rapport and listen to them.
The key here is asking really good thought-provoking questions that will open them up to you.
When I first discovered this years ago, it was a revelation to me. I remember going to a wedding and absolutely GRILLING an old friend with questions.
“What are you up to now? Where are you living? What kind of place? Is that an apartment or a house? How much is the rent? Blahblahblah.”
Eventually, someone else in our group commented, “Damn, are we at a job interview?” and everyone laughed. I thought to myself, “Man, I really miscalibrated that.”
I found myself guilty of TMQ [too many questions]. It’s a big problem.
Asking questions can be a great way to provide a springboard for active listening — and consequently, good compliments. But if you ask too many prying questions, you’re going to come off as just plain weird.
What you need to do, then, is ask a couple of really genuine questions — and then ADD to the conversation. If you’re having trouble coming up with questions, I wrote an entire post complete with scripts and situation-specific examples.
BONUS: If you really want to exercise your social muscle, check out my video on improving your social skills. It’s less than 30 minutes.
Step 2: Analyze their answers
When you watch people who are really socially skilled converse, they will ask a question, listen, and then make a statement based on that answer.
If you’re still confused, a solid rule of thumb is to ask 2-3 questions and then make a statement as well.
When you’re talking to someone, think to yourself, “Where can I add value? What connections can I draw between us?”
Take a look at the two examples below. Can you see why one is bad and the other one is good?
You: “Where are you from?”
You: “How long have you been there?”
Them: “Two years.”
You: “Oh, do you like it?”
Them: “Yeah, I really like—”
You: “What brought you here?”
TERRIBLE. This conversation is entirely hypothetical and I’m still cringing in my seat. You’re not involving yourself in the conversation — and as a result, you’re not adding value. All this does is make you seem like someone who simply asks questions. Don’t do this.
You: “Where are you from?”
You: “Oh, I’ve been to Michigan before. I actually grew up in Phoenix but live in Chicago — pretty close by.”
Them: “Oh, really? How long have you been there?”
BOOM. Now you’ve successfully engaged this other person and established a connection with them — all by sharing something simple about yourself.
Step 3: Give them an observational compliment
Once you’ve listened to them, you’re now prepared to give them an authentic compliment.
Here’s a great example of one:
You: “John, you seem a lot more thoughtful than most people I’ve met.”
Them: “Why’s that?”
You: “After talking with you, I noticed you really take the time to listen to what other people have to say.”
Notice how the “observational” part means that you OBSERVED something about them and responded with a genuine compliment.
And be honest with them. You don’t want to tell a ramrod-straight military general that you can tell he’s a sensitive soul. Likewise, you don’t want to tell a 9-5 office worker that you admire how adventurous they are (unless they ACTUALLY are).
How to give the perfect backhanded compliment
Ah, now the fun part! You got the basics down, so let’s analyze one of the backhanded compliments above: “I love how the design of the site itself is a lesson in saving money,” by Moshe.
He does everything right from the how to give compliments steps above:
1) Ask questions and listen: Moshe has read the site and my book. He knows I am all about saving money in smart ways.
2) Analyze their answers: By reading the posts, he knows I like to focus on big wins and automated savings. He also sees the old site design and it was a bit rough.
3) Give them an observational compliment: “The design of the site itself is a lesson in saving money.” Viewed without irony or sarcasm, this is a great compliment. However, Moshe used the optional fourth step of giving a compliment to twist this one into a backhanded compliment.
4) Add sarcasm or irony to change the compliment from positive to negative: Moshe has sarcastically twisted the meaning of his compliment from negative to positive by implying the site is ugly. This is the twist that all backhanded compliments have — a subtle change in context from positive to negative.
My favorite backhanded compliment ever follows these steps perfectly. Winston Churchill once said, “You can always count on the Americans to do the right thing after they have tried everything else.”
This is a pretty sick burn. Churchill (if he actually said it) starts by observing that Americans are moral and helpful, “You can always count on the Americans to do the right thing,” and then adds a sarcastic twist, “after they have tried everything else.”
Complimentary action steps
Here’s what I want you to do after you read this article today:
Compliment ONE person you don’t know in an authentic way today.
Remember to listen, analyze, and then compliment. Once you do, observe how it makes both you and the person react.
Then, for fun:
Compliment ONE person you DO know in a backhanded way.
Be sure to tell me how you did with both attempts. I love hearing about the great work that my readers are doing on their self-development journey. After all, we all started somewhere.
Bonus: I remember I used to feel uncomfortable and out of place during social events too — but over time, I’ve developed hacks for confidence in new situations. I’ll show you exactly how I do it in these 3 short videos. Just enter your email for instant access.