The other day after class, one of my students asked me about letters of recommendation. Oddly enough, she didn't want to ask me to write for her, rather, she wanted to know what she should give her writers to help them write the best letter possible. It's a great question.
I don't pretend to be the best writer of letters of recommendation out there, but I've written a few, and read some, so I have some ideas about what makes a good one. The best letters of recommendation give a sense that the writer knows the student well; usually good letters give specific examples of a student's written work, class work, and perhaps some relevant information about the student outside of class. For example, the letter writer might talk about Joe's work as a tutor, or Anne's leadership in a student organization.
That's probably easy if the writer actually knows the student fairly well. And there, gentle reader, is the problem for most students. How well do your professors know you? Do they remember you from that class two years ago? If you're in a school of 2000 students, they may remember you. If you're in a school of 20,000, they may not remember you nearly as well.
Your job in requesting letters is to give each writer the tools to write you a good letter. It goes without saying that it helps if you've gotten A's and such. (If you're reading this and aren't actually at the stage of requesting letters, and aren't already an active contributor in classes, now's the time to start!) But even if you don't, you can help your letter writers write the best letter they can for you.
Take time to meet with your letter writer when you ask him or her to write for you. And be sure to ask what materials (in addition to the things on my list) you should provide. Meeting with the writer will help him or her remember you if it's been a couple years since you've taken a class with the person. It will also give you a chance to make sure that the letter writer can write you a good letter in good conscience. If the person hesitates, ask if s/he has reservations, or sees potential problems with writing you a letter. Take potential problems seriously.
For example, I had a student ask me to write him a letter for a professional program for which he'd done no academic preparation. He was in my office, so it was easy for me to quietly close the door and tell him that while I thought he was an excellent student and could, in fact, do that professional work very well at some point, I was concerned that he hadn't taken classes (or done other work) to prepare him for such a program. I explained that while I could write a letter about what a great student he was in general, the people reading his application would wonder why he hadn't taken steps to prepare for that program, why he didn't seem to be interested in the profession enough to be working towards the program already. I noted that he'd be competing against others who had put in serious time to prepare for their program.
Happily, the student listened to my concerns and realized that he was unrealistic in his expectations. He decided to make some changes in his planning to prepare himself for the kind of career he wanted.
I've also had students ask me for letters of recommendation whose grades or GRE scores just weren't up to par for entering the kinds of programs they wanted to enter. Again, part of my responsibility is to give students an honest sense of how their grades/scores compare. I've still written letters for some of these people, sometimes very good letters, but I'm able to be honest and ethical about the grades/GREs. (In at least one case, I was able to write a much better letter of recommendation because we'd had the conversation.)
(If you have to make your initial contact by phone, mail, or email, then give the person a context so s/he can remember you better.)
I'm dividing the materials I like students to give me into two groups, mundane and special.
The mundane group includes the information/materials people need to just get the job done: put your materials into a file folder of some sort with your name on it, so they're easy to keep all together. Whether you're asking for one letter or six, make sure you provide a cover sheet with addresses and due dates for each letter. Provide stamped pre-addressed envelopes if appropriate. Provide copies of forms. Some graduate schools will ask you to sign a form that says you will waive or not waive your right to read letters in your file. Decide which you'll do, and sign.* Provide a list of classes you've had with your writer, including the year and semester, and the grade you earned. If you've done other work with the professor, list that, too. Provide a copy of your resume or curriculum vitae (your "life's course," aka a CV, the academic version of a resume). If you're having the letter written for a career center file, make sure that the appropriate forms are included.
The special group includes things that will help you stand out in your writer's mind. As a start, you need a copy of your letters of application or statements of purpose. If you're applying for VERY different jobs, then give your writer that information. But if you're applying to three similar graduate programs or jobs, then give your writer one copy. Give your writer a graded copy of the best work you did for his/her class, and if appropriate, a copy of the paper you're turning in as a writing sample. Give your writer the titles and class information (and perhaps a paragraph summary) of other papers you wrote for his/her class(es).
This is the information that's really going to make you stand out and going to give your writer a chance to talk about you specifically. S/he can talk about the argument you made in your paper and how at the time, s/he thought it was [and here the professor quotes from his/her original comments]. You get the picture, right?
You may also want to highlight a few things from your CV to remind your writer that you worked for a student organization or something, though if it's important, you've probably also written it in your application letter or statement of purpose.
Timing is everything. Not really, but it is important. Give your writers your information a couple of weeks to a month before the first due date. Remember that many professors have raised the arts of procrastination to impressive levels, that they're busy; so don't be shy about gently asking if they've had time to get to your letter during about week three. With some professors, you will need to ask more than once. Don't take it personally.
*The waiver: I generally advise students to sign the waiver. You've asked people you think have a positive impression of you to write your letters. Unless you think they're incompetent (in which case, you shouldn't ask them), signing the waiver says basically that you trust that they're not incompetent. I'm willing to guess that a few people in this world have been abused in some way by bad letters, but I seriously doubt that not signing the waiver would have made a difference.