It doesn't matter whether you're applying for a job as a babysitter or a CEO. At some point in your life, you will need someone to express support for your credentials. As a letter writer, whether you're trying to help a colleague or an employee achieve a desired goal, you will be in the position of holding that person's future in your hands with the quality of your letter.
In the past two blog postings of mine, I've covered key topics related to the application process-- interviews and personal statements. This posting addresses that crucial third component to job hunting success. I'll show you how to use psychology to ensure that your letters provide that final push you need to get the position you seek, whatever it is. I'm combining advice for "requesters") "recommenders", but each can benefit. Requesters will learn how to ask more effectively for letters of support and recommenders will learn how to write more effectively. I'd also advise recommenders to share this blog with your students, employees, or advisees to help them get an inside track on the jobs and positions they most desire. This will also make your life much easier, as you will shortly find out.
Advice for requestors:
We'll use the common scenario in which a student or job hunter is applying for multiple positions. Many people applying for jobs, promotions, internship positions, or university admission apply to more than one at a time. For a competitive position you might apply to as many as 12 different places. However, even if you're only applying for one position, the same rules are in order.
The most important issue for you to consider is to decide who to ask for a recommendation. Are you better off with a higher-up person whose name is more widely known but who doesn't know you? Or would your letter be stronger if it came from a lowlier source who knows you extremely well? One approach is to have the lower-ranking person actually write the letter which the higher-up person then signs. The problem with this approach is that it can be construed as unethical. The famous person doesn't know you at all but is giving the impression to the reader that he or she has observed your actions on a daily basis and can vouch for your terrific qualities. A way around this dilemma is to have the higher-up person author the letter and in the body of the letter, state that he or she is relying on the lower-ranking person's say-so. In this case, though, you would be well advised to make an appointment with the big shot so that you have made some actual, direct contact. This strategy is actually an excellent one from a psychological point of view. By making this personal contact with the big boss, you might wander into some new and unexpected opportunities for advancement.
You might wonder here about timing. If you finish one job or school position and don't need a letter right away, but will in the future, when should you ask for it? My advice is simple-find out what your recommender prefers. I personally think generic letters of recommendation that don't address a specific position aren't all that good, so I suggest that people wait and ask when they need the actual letter. In the meantime, stay in touch with your recommender and don't just contact him or her solely for the purposes of getting the letter. That way, the person is sure to remember you!

Alright, you've got your recommender(s) lined up. Time to pop the question. Make the request in a straightforward, simple, clear, and organized manner. Put it all together at one time. Don't ask for a letter for one position on Tuesday and another letter for a different position on Friday. Don't ask for a letter and then announce a couple of weeks later that you changed your mind and no longer want to apply for that position and now need a completely different one. If you know that you are applying for several positions, wait until you have all the relevant forms and info to distribute.
When you make the actual request, ask if the recommender feels comfortable writing you a good (i.e. positive) letter for the position. Your closeness to the recommender will determine how you actually word the request. If you get a "no" or sense some reluctance, you might want to reconsider whether you should ask this person to complete the recommendation.
Let's hope the answer was an enthusiastic "yes!" Put together in an easily accessible manner all of the documents that you submitted for your application and give these to your recommender. Find out if your recommender prefers to see these as hard copy or as e-files and then send them in the preferred manner. These documents should include, as necessary, your own personal statement, your resume, and your transcript (if required). They should be the exact documents you submit in your application. I also advise you to indicate, either in your request or as a separate document, the exact nature of your relationship with the recommender. Professors and employers won't have in their heads the dates of your work together, but they are usually asked to provide this info in their recommendation. Don't make these people have to guess or consult their records. Again, from a psychological point of view, your attention to these details will show that you actually are organized, attentive to detail, and have all the other positive qualities about yourself that you want the recommender to verify. It's great impression management to be organized when you're asking for something important from a boss.
With regard to the actual forms themselves, some positions require letters only; others involve complex documents with multiple parts which are either online or paper. If hard copy letters are involved, provide a list of all people to whom the letters should be addressed. Give the recommender stamped, addressed envelopes and put the return address of the recommender on the envelopes. Make sure that everything you've obtained is up-to-date and accurate.
Here's another common question: Do recommenders resent being asked for multiple letters from one person? The answer is no, they do not. Most recommenders don't mind adapting the basic letter they've written to the specific purpose. However, make sure that you remind the recommender to proofread the letter before sending it off. A letter that says you'd be a great employee at Gotham City Bank would not go over very well if read by an employer seeking to fill a position at Metropolitan Bank.
If forms are required in hard copy, put them neatly in order in a folder along with their envelopes. You can get creative with the way you organize these by color coding or using attractive notebooks or file folders. For online requests, you won't have to do this. But if there is a mix of online and hard copies, then you have to include the online form descriptions in this little portfolio you prepare for your recommender. Psychologically, this step is important because you are reducing the cognitive load on your recommender. People trying to help you in your career are probably busy, and will appreciate this courtesy. They'll also be less likely to make mistakes.
Occasionally, recommendations are requested over the telephone. There are sometimes issues of confidentiality in phone or email requests. You need to assure your recommender, in written form , that you waive your right to see or find out about this communication.