Letters of Recommendation: What Not To Do

Last week’s inaugural L.A.W.S. events were, as I’ve already mentioned, terrific successes. The element that I thought was potentially most helpful for attendees was the panel of admissions deans giving advice at the outset each night. (In an effort to convey exactly how much knowledge undergirded the opinions, one wag added up the total years of employment of all the admissions deans at the attending schools; it was a truly appallingly large number that I choose not to repeat here today.)

But when it was my turn to be on a panel, the moderator’s query as to what would be my one bit of counsel about what NOT to do drew from me only a mortifying blank stare. I have excuses for this. For one thing, I don’t always love the what-not-to-do format1 (although I really loved the timeless advice of Dean Post from Penn not to begin emails with “‘Sup”); it sometimes ends up sounding shrewish or smug. (The Wheel of Fortune contestant application, for example, instructs: “Don’t tell us that being on Wheel is on your bucket list.” That just seems unnecessarily rude to the enthusiastic Wheel aficionado. It certainly discouraged me from applying.) Also, the panel had already doled out some advice on the what-not-to-do theme, and I just couldn’t think of anything new. The result? After a few beats, I came up with, “Don’t panic.”

Slow Clap

What with being in the midst of panic myself at the moment, I could tell that panic was not helpful. L’esprit de l’escalier hit me about 15 seconds later, though, and has been with me ever since, with an ever-lengthening list of advice I could have given.

One bit I’m particularly sold on has to do with letters of recommendation; I found inspiration in the worst letter of the past season. It begins like this: “I have known Josephine Smith2 for 11 years.” Sounds promising! But the next sentence snatches away the apparent affirmation of Ms. Smith, making clear that the letter-writer only barely knows her, from her acquaintance with the letter-writer’s child during secondary school. What did the letter writer learn about Josephine through this pretty attenuated connection? Not a whole heckuva lot. Boiled down, the letter is a list of general adjectives and vaguely supportive statements, such as, “She makes people around her better.” All told, the letter was 13 sentences, concluding with these three: “Josephine Smith is a person who will be very successful. I am sure of that. I cannot assess legal aptitude but I know winners when I see them.”

This input is not helpful to a law school admissions decisionmaker.

The kicker, though? The signature block:


CEO, Truly Gigantic Company, Inc.3

At the risk of being tiresome, let me be completely clear: Instead of a signature, the letter contained the bracketed phrase, “.” The actual name of the letter writer was, presumably, to have been substituted for the bracketed phrase, but oopsy daisy, that didn’t happen.

On the one hand, I could mount a pretty strong argument for why this lame letter shouldn’t be held against Josephine. She asked a powerful, high-achieving person that she had known for 11 years to write her a letter, and he said yes, from which she pretty reasonably concluded that he was going to put more than five minutes of effort into the undertaking. Contrariwise, she might have assumed that five minutes of effort from that kind of luminary was going to result in a letter that looked like a two-hour effort from a mere mortal. But on the other hand—I’m a lawyer, remember, so this one hand/other hand stuff is impossible to resist—come on, Josephine. This person obviously didn’t know you well, and didn’t ever supervise you or interact with you in a setting where he was comparing your performance or character or skills to those of your peers. You knew that. You asked this person to write your letter in the hope that admissions officers would be so wowed by the name as to look past the contentless fluff. To be sure, his failure to actually include his name undercut that tactic. But you knowingly assumed the risk.

So that’s something not to do: Don’t ask powerful people who don’t really know you to write you a letter of recommendation, because it won’t serve the function a letter of recommendation is meant to serve: providing an external voice to validate your capabilities. And now here’s some corollary to-do advice: When you ask someone to write you a letter, make sure you give that person an out. Ask by email, and say something like, “Do you think you could write a strong letter?” (That leaves room for him or her to respond, “Actually, while I think the world of you, I don’t think I would be the best letter-writer in this context because, among other things, I cannot assess legal aptitude.”) Say also, “I know you’re really super busy so I will totally understand if the answer is no.” That before-the-fact permission slip is a kindness and a courtesy.

Now, your instinct may be to reject this advice. You really, really want a letter from this person—you need a letter from this person! What do you care if you’re a little pushy?4 In fact, however, you only REALLY want the letter if the person wants to write it. An unenthusiastic, undetailed letter is, at a minimum, not helpful, and depending on the other materials in the application, can actually hurt you.

There’s a basically happy ending here, though. Everything else in the application (including two other letters of recommendation) was beyond reproach, and I admitted Josephine Smith. Alas, Josephine decided to go somewhere else—but at least now I don’t have to decide whether to send Mr. Famous CEO a thank-you letter for his recommendation, which is my habit for all the recommenders of enrolling students. In his particular case, I might have made an exception.

1 I have been known to dabble in it, though. 

2 Word to the credulous: Josephine Smith is a made-up name.

3 Truly Gigantic Company, Inc. is also a made-up name. See supra, Josephine Smith.

4 In an early episode of The Sopranos, Carmela browbeats the sister of a neighbor to write a recommendation letter in support of Meadow’s college application. Watching this episode, I was fixated on the admissions issues. I wasn’t interested in the theme of how Carmela was exercising a domestic version of Tony’s coerciveness—all I could think about was whether the sister would say, “Sure, I’ll write that letter”—and then write a really crappy letter. That’s the passive-aggressive way to deal with mob pressure.