You may feel awkward asking someone to write you a letter of recommendation. Perhaps you're especially modest, or you hate to impose. Indeed, writing a reference letter is a favor of time and expertise. It takes at least an hour or two to write a good letter of recommendation. Particularly in the case of high school teachers and counselors, the letters will often be written on "their own time." However, recommendation letters are a part of academic and professional life, and requests are rarely a surprise.
Contact the person via phone or (if it seems appropriate) email. Explain why you need the letter, and what it will mean to you and your academic or professional career, or personal situation. You could make it easier by providing the writer with a copy of (for example) the scholarship application materials, fellowship announcement, job advertisement or adoption agency profile. Don't ever ask anyone to lie for you.
Try not to approach someone at the last minute to ask for a letter. This is especially true in the case of academic letters of recommendation, because deadlines are often known well in advance and because professors, teachers and others in academic leadership roles are asked to write many such letters each term. Giving the writer a month or two, or at least a couple of weeks, shows respect for the person's time and expertise. This may not be possible if, for example, you're applying for a job or coming up on a court date or other deadline.
Give the person a date by when you need the letter. Consider setting the "deadline" a few days or even weeks earlier than the real date, in case you need to ask for revisions (due to fact or spelling errors, for example) or in case the person forgets. It's not uncommon to have to remind someone that you need the letter. For this reason, it may be smart to get an "extra" reference-four letters if you need three-in case someone doesn't come through, or a letter doesn't send the message you had hoped. Don't forget to make sure the person has your phone number(s) and email address handy in case he or she needs to reach you about the letter.
If the person stumbles around and hesitates when asked if he or she can write a recommendation letter on your behalf, it could be due to reservations about endorsing you, or it could be something as simple as the person being very busy. If it's the latter, you can make it easier by providing the letter writer with background information such as: academic transcripts, job history (a resume), list of awards won, biographical information and so on. If the letter is for an award or scholarship, give the writer a copy of the description and guidelines or a link to a web site. High school students can include a note with their request mentioning what they perceive as their best personal and academic qualities, as well as accomplishments and extra-curricular activities and a statement of goals and ambitions. College students can refresh the writer's memory about projects worked on and essays written, as well as career aspirations and other relevant points. The more information the writer has about you, the better the letter can be.
While most experts agree it's preferable that the letter truly be written by the person who signs it, it's not uncommon for the person being recommended to give the writer some talking points, or even write the entire letter and get it approved and signed.
But if you perceive (or can confirm) that the person would not write a glowing recommendation, or would "damn you with faint praise," it's best to say thanks anyway and walk away from the situation. This is especially true in cases where the letter is sent directly to the decision makers without you first getting a chance to review it. This is often the case in high school settings, where many consider letters of recommendation "confidential documents" sealed or sent straight to a college without the student getting a chance to read it first. You might even have to sign a waiver allowing this. Some consider it inappropriate for students or parents to even ask to read the letter, so find out what is customary before approaching a teacher or counselor for a letter. If the letter is to be sealed and/or mailed directly, provide a pre-addressed envelope and stamp for the writer's use.
Some might feel asking someone to write a letter of recommendation is an imposition, or, at least, an inconvenience. But it's likely that at some time early in that person's career, someone took the time and effort to write him or her a reference letter. If someone truly thinks highly of you, he or she will be happy to "put it in writing."
It is very important, as professional courtesy and common courtesy, to thank the person for writing a letter on your behalf. It needs to be clear that you appreciate their efforts. Thank him or her very soon in a letter or card, not just verbally or via email. It's also nice to let your references know how it ended up-whether you got the scholarship, job, etc.
Index of letter of recommendation templates