(This could easily be titled “How To Win Friends And Influence People”, but that one is already taken.)

If your colleague, friend, or family member has asked you to write them a letter of recommendation or reference, it is because they think they have fooled you out of knowing The Real Them. Or because you are erudite and savvy to the ways of the professional world. If it is the latter, congratulations! Here is your chance to demonstrate your wit and creativity atop your already legendary erudition. (May we operate under the assumption that you desire the best for your colleague, friend, or family member, and hope this letter helps them gain the position or admission to which they’re endeavoring? Oh good. Otherwise: eesh.)

Wanting your companion to succeed, you will try to write a glowing review of their personality, character, and abilities, but you know that every other candidate will likely present a letter of reference that glowingly celebrates their every utterance, blink, and bowel movement. How, oh how, to cut through the noise? Firstly, do not write:
“Glen is punctual, hard working, and easy to get along with.”

I just fell asleep typing that sentence. If I were Glen, I would second guess every decision I ever made that led to me requesting this favor of you, and all that second guessing is hard on a marriage, and you don’t want that on your conscience, do you? But maybe the three qualities you most appreciate about Glen are his punctuality, work ethic, and enjoyable mannerisms! If so, I would wager that you are maybe a bit boring, but that’s okay. Here’s how to communicate such commendations in a way that will make Glen irresistible and make you the greatest friend Glen has ever had. Try this:

“Glen is strange: he believes ‘on time’ is actually something a person should be. He knows his work reflects him, so he makes sure it’s done right every time, and Monday or Friday, over time or holiday party, the guy is just really nice to have around.”

You have successfully expressed Glen’s punctuality, work ethic, and charm, but you not only kept everyone awake, you made sure they all developed tiny crushes on Glen. Well done! Breaking it down, the mild use of misdirection (“Glen is strange”) is especially effective in a reference letter because it is particularly unexpected. These letters are almost always straightforward, except when they are dripping in euphemism and hyperbole. Not only is Glen punctual in this example, he is punctual as a point of principle. (Why yes, that IS a lot of Ps!) Glen is no longer the on-time robot, he is the gentleman of yesteryear, when your “yes” meant “yes” and your 4pm Greenwich Mean Time was 4pm Greenwich Mean Time. Well done, you! Glen is on fire.

Moving on: Glen has a great work ethic because he takes a wider perspective on his work and isn’t just punching the clock. You didn’t claim, as some other applicants’ letters will, that he nails it on every first try; you expressed Glen’s commitment to the process, and to problem solving. This saves you the trouble of later finding a more writerly way of saying “Glen is a good problem solver”, which very nearly had me nodding off again! Finally, you demonstrated Glen’s likability through a broad array of situations. If he’s as enjoyable at 7pm on a Monday as he is when you’re all knocking back spiky egg nog and watching Denise and Lamar realize long-held passions, it means his appeal has an ease to it- there’s no pressure to like Glen, but you do anyway. Yes, you used several more words in this version, but you also communicated significantly more about Glen. Perhaps most importantly, you made yourself more attractive (as if that’s even possible- just look at you!), and everyone trusts the opinions of us Attractives. The more your comrade’s potential boss likes you, the more they’ll like him/her. It’s science.

Let’s look at an example from reality. My dear friend Jenna asked me to write something for the ‘about me’ section of her online portfolio. Jenna is a commercial interior designer, so she dances the tightrope between flexible, artistic expression and the confines of the modern business dealing. My experiences with Jenna were social and collaborative: we were both members of a philanthropic organization that promoted culture in our town. I haven’t met many people like Jenna, so I wanted to communicate her verve and magnetism. (Verve and magnetism are excellent adjectives to apply to someone who deserves them.) I didn’t need to speak to her abilities, because her portfolio would do that, so I just described the general Jennaness of her:

“Jenna is an enviable blend of charisma, optimism, and wide perspective. She is a pilgrim and a sponge. She would leap tall buildings but she’d much rather meet the people inside. She divides her time between enjoying the marvelous and making marvels herself, and she only stops for feedings.”

Balancing a sentence that lists several somewhat-nebulous attributes with a succinct declaration is a good way of showing just how well you know your subject. A list says, “she is these things at different times” and then a statement, well, states. Your reader will appreciate your definitives; they wouldn’t be reading if they didn’t need to know what you know.

It’s also effective to tell the stranger what your compatriot is not or will not do, and not in the sense of, “Jenna is averse to setting kittens on fire. She also does not steal post-it notes from her employers.” Your letter will include many things the subject is and is capable of; including a positive attribute or habit that may be outside of his/her wheelhouse will engender the reader’s trust, because you are being honest. I indicated that Jenna was disinclined to leap tall buildings, because, while Jenna is a go-getter, she is moreso a member of the planet-wide community. I decided that her portfolio and job searching efforts would sufficiently speak to her ambition, and that my reiteration would be superfluous.

Similarly, if you are writing your missive for someone who is shy or simply introverted, please do not treat these qualities as shameful secrets. You are well within your boundaries to say, “Carlo is not likely to be the office Homecoming King because, while he is witty and kind, he does not desire a great deal of attention. In time, you will appreciate him as a friend as much as I have.” If your letter reaches the reader before Carlo does, this will prepare them for a modest interviewee and will spare your subject considerable pressure. As an introvert, I can assure you that this may be the greatest gift you give to someone, short of a high-quality espresso machine for Christmas or Hanukkah.

(Incidentally, Jenna landed a wonderful job shortly after moving to Denver. Was it all because of my description of her? Yes. Yes it was.)

But what if you are petitioned to write a review of someone for whom you have little to praise? Awwwwkwaaaaard. You’re an honest person, you don’t want to defraud the future employer or educator of your acquaintance, but perhaps you don’t have the social flexibility to tell your supplicant that, no, you will not assist them in this effort. I don’t envy your position. I might even feel a bit of schadenfreude from it all. Nevertheless, I have suggestions for you.

It is unlikely that your associate has no merit whatsoever. We all have merit (especially you and I, if we’re being honest). Few people are unself-aware enough to not have any idea of where they stand with another person, so if this seeker has requested your acclaim, it’s because at some point, by farce or unconsciously, you implied that you had some to give. Dig deep, dear. Find the lie or the flicker in your unconscious that briefly shone upon this poor, near-worthless wretch, and discover it. You may want to write,

“Alas, dear sir or madam, Oswald is inept. Basic instructions seem beyond his comprehension. Personal hygiene is not something to which he endeavors. Social mores escape him entirely. Indeed, he succeeds only at flummoxing everyone at all times.”

But I believe you can find the pearl buried deep within the slimey, bottom dwelling reality that is Oswald. (Incidentally, I adore the name Oswald and intend no judgment of any actual Oswalds, most of whom I am sure are darling, daring, or at least adequate.) Is your Oswald always late? Well at least he comes to work or class at all. Try: “Oswald seems immune to the apathy that plagues his generation. Where most of his peers seem wholly disconnected, there is a point in Oswald at which hope remains.” Is Oswald distinctly unintelligent? (It’s okay to say yes, this is a safe place.) Consider something poetic and compact, like, “Oswald is a human spoon”, wherein you are saying that he is not sharp, but probably useful for soft things. Is your Oswald rude? (For shame, Oswald!) First, confirm that what you perceive as rudeness is not ignorance of social expectations borne from an alternative upbringing, or that it is not the expressions of something like Asperger’s Syndrome. If Oswald is truly rude, as several people are, I cannot, in good faith, argue for shielding the reader. But! Maintain your tact and eloquence, even in the face of uncouth Oswald. Write, “Oswald lacks grace and manners, though I am certain this condition is reversible.” We are, indeed, all capable of goodness.

Finally, here is a recent reference I wrote for two friends who plan to travel. They wish to use Airbnb to facilitate their journeys, and it requires references to your character. Having known my friends for many years, it was an easy reference to write. I include it here because it showcases how not all of these projects must remain within the confines of formal correspondence. It also says a fair bit about me, explicit and implicitly, which I’ve already mentioned is significant for the reader. Oh, and their dog is included because she intends to travel with them.

“Ohhh, the Rostens. The boy half I’ve known since I was 16 and the girl half I met when the boy half married her 10 or so years ago. I might like the girl half better? but the boy half pretty much made my career, so… it’s complicated. These two like stories and things that are lovely only because they are true. They travel to fill their quota of loveliness and stories and lovely stories.

Lyn is the brains and Jesse is the sponge, but they swap hats a lot. Except the brains hat- that usually stays on Lyn. I have travelled with them several times, and I am a very neurotic traveller: they are gracious people. They love science and art, and people who love science and art are not destructive. Team Rosten seeks and explores, but not aimlessly, and they’re inclined to be fans rather than critics. They maintain perspective pretty well: I don’t think I’ve ever seen them spend money on something that wouldn’t better them more than the money saved would have.

I lived around the corner from them for 5 years. Their dog is my dog’s only friend because my dog is an emotional porcupine; Stella was optimistic enough to give her a chance. Stella is fastidious and loyal and keenly aware of the power of opposable thumbs. I cannot say much about the motorcycles, except that they match and are not Harley Davidsons. Team Rosten is ambitious, creative, and kind, and I would have them raise my two children if we did not disagree so passionately about avocado.”

And there you have it, my attentive visitor. You may never know if your letter opened the door to someone’s dream, but oh, to try! And if it succeeds, the karma you will reap could be immeasurable. The parking you’ll enjoy is just the beginning.