Complimentary, my dear Watson

Most everyone loves to receive a meaningful compliment.

"I love your new haircut!" is a solid-gold stamp of approval and provides confirmation that we made the right choice at the salon.

Every budding author longs to hear: "You are a really talented writer. Have you ever thought about writing a book?"

The boast every employee hopes to receive from their boss is: "Fantastic job on the proposal for the new work project. It is a creative solution that could take this company into the next tier of success!"

Meaningful compliments carry us up onto the clouds of self-esteem -- we've been seen and we matter. Our work or choices have met with enough approval that the other person chose to shine a spotlight on us with their uplifting words. Who doesn't love the warm glow of someone else's approval?

In my experience, paying compliments can either be a successful social habit with payoffs well beyond the moment the words are spoken -- or they can a tool of manipulation. There are a few kinds of compliments that have varying degrees of authenticity and success in making the other person feel admired.

• The "Backhanded Insult" Compliment -- Some compliments sound nice on the surface, but are actually kind of insulting. These are the compliments that applaud some change in the hearer while implying some previously-held disapproval they had never shared with you. "You look so great! You've lost so much weight!" is a Backhanded Insult Compliment. While the person dishing out the praise probably means it nicely, it has the unintended outcome of making the hearer feel like they must have been previously viewed by others as unattractive and fat. Another example is one I have loathed at family gatherings before I met my husband: "You're such a pretty girl. I don't understand why no guy has ever married you." I don't think I have to explain how that one feels insulting to the recipient who may not love to have a spotlight shining on their singleness as though it were a tragedy. 
• The "I'm Tricking You Into Working Harder" Compliment -- I had a boss who employed this habit very heavily. She had a sweet southern drawl and her voice always sounded like it was dripping in honey butter when she spoke. Most people felt very warm toward her and saw her as having a real "way with people". But after only a short while as her employee, I began to notice that she only paid compliments if they were followed by a request to do something. "You're so organized -- probably the most put-together person in our department! I was hoping you would work your magic on the file room." The person receiving this compliment (especially delivered with a Sticky Sweet Southern Drawl) might feel puffed up with pride over a job well-done....until they are neck-deep in the Hell of the file room. There's a reason the boss wanted you to work your magic. No one else would touch that mess with a thousand-foot pole. If you only pay compliments to get others to add to their workload or to volunteer for tasks they might not otherwise have chosen to do, then you might be crossing the line into a manipulative compliment style that will eventually become transparent (and irritating to others).
• The "Sleazy" Compliment -- I like to be told that my hair looks nice and compliments about my outfit are always appreciated. However, I don't think I am alone in saying that I loathe compliments that sound as sleazy as catcall. Telling a woman "That dress really makes your assets look like a million bucks" isn't a compliment any woman wants to hear from her boss or her weird uncle or a random dude in the parking lot. If a compliment sounds even a little sexual, it probably shouldn't come out of your mouth unless you already have a sexual relationship with the person you are complimenting. Telling my husband that a pair of jeans makes his butt look sexy is a heckuva lot different than giving the same compliment to the cashier at Target. (Side Note: some BFF's have a relationship that involves this style of compliments, which is totally acceptable given the depth of the friendship).
• The "Ramp-Up to Negative Feedback" Compliment -- A few years ago there was a sitcom that featured a character who routinely did the "compliment sandwich" to deliver bad news to others. For instance, when breaking up with a girl this character would start with a compliment, then deliver the one-two punch of the break-up news before ending with another compliment. Here's how it would go: "Holly, you are such a pretty, sweet girl. You deserve someone better than me. I think we should stop seeing each other so you can find someone who really deserves someone like you. Some guy is going to be so lucky to have you as a girlfriend." I find negative feedback really difficult to deliver because I hate disappointing others for fear of ruining the relationship. The Ramp-Up to Negative Feedback Compliment softens the blow and makes it feel less scary to deliver constructive criticism. Plus, if done well, it can strengthen the relationship when the hearer realizes you care enough about them to deliver hard news in a loving way. While no one especially loves criticism, sometimes it is necessary to help us succeed. After all, wounds from a friend are better than kisses from an enemy (Proverbs 27:6 Tina Paraphrase Version).
• The "To No One In Particular" Compliment -- In my work history I have had several bosses who routinely utilized this style of adulation. Typically, you only hear this style of compliment in groups. I had one particular boss who rarely handed out individual compliments to anyone. Instead of telling Super-Star Sally that he appreciated her specific, unique contribution in improving something in the workplace, this boss would compliment the whole room of employees during the weekly staff meeting. "Thanks for all you do...every one of you. This company wouldn't be the success that it is without dedicated employees like all of you." Lets be honest, though. Super-Star Sally is probably one of the bright spots on a work team that likely also includes some dead weight like Blathering Bob, Parties-Too-Hard Pat, Twitter-Troll Thomas, and In-Over-Her-Head Irma. Did they deserve to share in the glow of a compliment which really belongs to the one employee in the room who actually works eight hours a day? If you want no one in the room to feel particularly complimented, then you should definitely keep using the To No One In Particular Compliment style.
• The "Not Actually True" Compliment -- Every parent is guilty of the Not Actually True Compliment and if you think you're not then all the "amazing art" that's currently lining the bottom of your recycle bin begs to differ. Sometimes we have the best intentions in paying a compliment, but shoot ourselves in the foot by paying a compliment that we don't actually mean. Telling someone that their new haircut looks great on them might seem like the nice thing to do, unless the haircut is the worst thing that you have ever seen. Or telling someone that everyone loves their lime-apple-pumpkin salad is cruel if they ever find out that their "delicious" dish goes straight into the dumpster every time it shows up at the potluck. Pretty soon, folks begin to doubt all compliments they hear from folks who use too many Not Actually True Compliments.
• The "Conversation Starter" Compliment -- As an introvert I often find it difficult to initiate conversations with people I don't already know. Over the years, however, I have learned a trick to start a conversation using a compliment. I quickly take stock of the person I need to converse with to see if anything stands out as (a) worthy of a compliment, and (b) something we could talk about beyond the initial complimentary statement. For example, say the person is wearing a cool t-shirt that looks like it might have been purchased while on vacation. I might go in with a compliment about the shirt and then the person might respond with "Thanks. I got it while on vacation in (fill-in-the-blank)." Then the conversation might progress by talking about a shared experience if I have been to the same place or asking questions to get more information if it is a place I have never been. Or let's say that I notice the person is reading a novel that I have read before. I could pay a compliment like "Great choice! I love that book!" Then I could continue the conversation by asking what part of the book they are at or we could talk about the movie adaptation of the book. I have actually taught the Conversation Starter Compliment to children at a school where I worked. It was such an effective lesson that a severely autistic student was actually "caught" by her special needs teacher using a compliment to talk to a peer -- something she had never done before! Because people generally love compliments, this is usually a very successful way to begin conversations.
• The "Friendly Quickie" Compliment -- Most compliments are your run-of-the-mill quick sentiments that don't require too much thought or investment. When I worked in school settings, I considered it my main job to encourage others, which means I was a complimenting machine. Teachers (especially "special" teachers like the counselor or art teacher) usually have some sort of duty they have to perform beyond their normal teaching duties. My most favorite duties were the ones that allowed me to greet kids in the morning. I tried my best to say encouraging things to kids as often as possible, which means I was constantly watching out for new haircuts, cute shoes, interesting t-shirts, cool backpacks, nifty show-and-tell items, and other details I could say something about. This is different from the Conversation Starter Compliment in that I wasn't looking to begin a dialogue with these quick compliments. Often these Friendly Quickie Compliments turned my students' tired/bored expressions into smiles that they then carried down the hall. Sometimes, the compliment they received at the door was enough to cause a compliment landslide around the building as kids passed their good feelings onto another kid, which would then spread outward from there. 
• The "Heart Melting" Compliment -- These are the rarest of compliments and usually the ones that carry the most weight. This is a compliment that is specific and filled with genuine appreciation and admiration.  I have had a few students over the years pay me Heart Melting Compliments. I once had a student tell me that she wished I was her mother because I made her feel loved in a way that her own (sadly) neglectful parents didn't. I had another former student tell me that she felt her life was changed for the better when I once mentored her as she prepared to give "sermon" during the chapel service at the Christian school she attended. It boosted her self-esteem and set her on a course of pursuing other ways to use her faith to empower others. These compliments weren't to impress me or win my approval or get me to do something for them -- they were just genuine expressions of their deeply felt admiration.

If you want to be effective at giving compliments that matter, check your Compliment Motive. Are you looking to get something out of the compliment (like getting someone to do a job no one else wants to do)? Or are you looking to bless the other person in a big or small way. If your motive is one of blessing, then get cracking on those compliments because they are a great way to show kindness and spread a little cheer. And, especially for those who need a reliable conversation starter, compliments are also a great social skill to have in your arsenal. Do keep in mind, however, that compliments have to be genuine to be effective. Nothing ruins a compliment like knowing the other person doesn't actually mean it.