Letters of Recommendation - How to Ask for (and Receive) an Exceptional Letter

It’s almost that time again - college application season. When students across the country and the world submit applications to their dream schools, fit schools, and everything else in between. College Board estimates that the Common App platform alone sees about 1 million students submit about 4 million applications - and that’s not even including other application platforms or schools that accept applications directly.

By this point in their high school career, students should be familiar with the basic requirements of the college application - the essays, the application forms, the transcripts, etc. And although students understand the importance of letters of recommendation, they often overlook some of the most important questions to ask themselves about these letters. Instead, students focus on only one question: “who?” Whom should I ask to write my letter of recommendation? It’s a very important question, but it’s not the only important question that students should be asking themselves about their letters of recommendation.

Who should I ask?

Since it’s the first question (and often only) question in students’ minds as they look to check this requirement off their application to-do list, let’s talk about who. Whom should you ask for a letter of recommendation? Students and parents often make the mistake of bee lining straight for the “most prestigious” person in the student’s life: a principal, celebrity, or influential relative. But these are not always (or even often) the best choice. Step back for a moment and consider the purpose of a letter of recommendation. It is not to assess the student’s social clout or see how connected they are. Colleges want information that will help them assess the intangibles of a student’s character. Are they generous? Are they curious? Are they a team player?

To answer these questions, the student should prioritize letters of recommendation from adults at their school and in their life who are able to speak to these intangible qualities. The most important thing is that the recommender knows the applicant well enough to talk about who they are as a person. You may have seen the news story from 2017 of the high schooler who got into Dartmouth with a letter of recommendation from the school janitor. What’s important is not the status of the recommender, but their relationship with the student. Find a teacher that you know well and who knows you well. Do you frequently interact with this teacher outside of class? Can this teacher speak about you on a more personal level compared with other teachers? Your recommender should be able to describe your character in detail - not just say vague, positive things.

When should I ask?

But just as important as the “who” is the “when.” Even the most positive of recommendations can be ruined if you drop the request in the recommender’s lap over email 24 hours before the recommendation. Or even worse - forget to send that email and list them as a recommender, anyway.

You should prepare your request well in advance, around 5-6 weeks before your letter must be received. Not only will this give your recommender plenty of time to write you a good recommendation, you will give them the impression that you value their time and want to help them help you. Additionally, this allows them to take time to “study” you more intently and get a good idea of your character. There may be a good anecdote they can include on the recommendation that they might not have remembered if you had not primed them to note it down for this purpose. On the other hand, if you wait until the last minute, they might feel rushed and the quality of your letter may be compromised.

How should I ask?

One of the biggest mistakes we see students make is simply asking for “a letter of recommendation.” This is not enough. When you contact your recommender - by email, in person, or otherwise - always ask for “a positive letter of recommendation.” This might seem disrespectful - like you don’t value their opinion unless they are willing to say good things about you. But the truth of the matter is, you do not want this person to send a negative letter along with your application. Just as bad can be a teacher who feels uncomfortable rejecting your request and writes a letter that is less than good but not quite negative. College AOs will read between the lines and realize what has happened - that the teacher was not willing to recommend you but was asked to do so, and so they sent in an ambivalent letter.

Asking for a “positive” letter also gives the teacher the chance to say no. By specifying that you are looking for a positive letter, you give the teacher a chance to tell you that they would not be comfortable writing a positive letter. This may seem like a bad thing, but it’s not. A teacher who is not willing to write a positive letter will never be a good reference. It is much better that you know early in the process, so that you can find a replacement for that recommendation.

The other important thing to remember about contacting your recommender is that the form should be appropriate to the medium. What does that mean? It means that the way you speak or type should fit the method you chose to contact that person. An email is a formal mode of communication. It should have a salutation (Dear ____,) it should have a complimentary close (Sincerely,), and it should include your full name. Remember - even if you’re asking the goofy art teacher who puts their students’ work on the walls of their classroom, that person is still a professional and you are asking them to take time to do you a favor. Show that you respect them and appreciate their efforts!

What should I send?

As you may have guessed, the answers to a lot of these questions are about making the recommender’s job as easy as possible. Anything you can do to make this a pleasant process for them will result in a more positive letter for you. That’s why once your recommender has agreed to write a letter for you, you should send them all the materials they might need to do so. Even if this is information they could find for themselves, remember: they are doing you a favor. Take the time to make it easy for them. Be sure to send any forms that need to be filled out, let them know if anything needs to be done in hard copy (not very common these days), and any attachments or supporting documents they will need to send. If they have all of that information in one place on your email, they can focus more on writing a great letter!

To help with that last bit, you should also attach a small “cheat sheet” to your email. Think of it as a page of notes that you would bring to an open-book test. This cheat sheet is basically your student resume. (Yes, you should have a resume as a student; we’ll talk about that in a later post.) Never make the assumption that your teacher knows everything about you. They might know how you did in their class, some stories you’ve shared with them, or even about your extracurriculars if they sponsor a club you participate in. But there are going to be parts of your life that they are not aware of. Sending that information to them makes it even easier for them to piece together what they know of you and present a fuller, more nuanced picture to the colleges of your choice.

In addition to your resume, you can even include a “cover letter” of sorts. This can be a place for you to talk about any personal experiences you’ve had that you think are important and will show up in your college essays or elsewhere in your application. Or you can tell your recommender what majors you plan on applying for. Or let them know what you value about your relationship with them and make you want to ask them for a letter of recommendation. In short, do a little work to put your request and your application in context for your teacher so that they can present you in a way that supports the rest of your application.


Follow all of these steps, and you’ll have the best possible recommendation from the best possible recommender for you. And remember - the point of the college application is to explain who you are to the school and show them why you would be a good fit in their community. Letters of recommendation, along with your essays, are the chance for your personality to shine through the fog of numbers and classes that make up the rest of your application. And it’s not just your recommender’s responsibility to create a good recommendation - this is something you have to take ownership of, too. Don’t waste this opportunity by setting up your recommender to fail; give them what they need to succeed!

Veritas Education College Planning

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