One important step for college-bound students wrapping up their junior year: request those letters before the year is out!
When do recommenders typically write letters?
The vast majority of recommenders write their letters during the fall. However, there are some very industrious and forward-thinking recommenders who will actually write at least some of their letters over summer. Remember that (a) your teachers who write your rec letters do it as a personal favor (i.e., they're not paid for the time they spend writing); (b) it's always better to give someone doing you a favor plenty of time to do it so that they don't feel rushed; and (c) the earlier your recommender writes their letter about you, the more energy and enthusiasm they're likely to have while doing it.
In other words, regardless of when your recommenders will write the letter, the sooner you can make the request, the better.
What do they need from me?
Most high schools put into place a series of deadlines by which you need to have requested your recommendation letters and submitted some supplemental materials, such as a brag sheet, cover letter, and/or list of colleges you'll apply to. Some recommenders will actually supply you with their own questionnaire so that you can spell out exactly what you'd like for them to convey about you.
Don't skimp on the work that you put into these materials! Remember that your recommenders, because of their adult perspective and area of expertise, add a lot of dimension to your overall application. If you have all the content teed up that helps put your best foot forward, using it will make their workload much more manageable.
When do I request them?
NOW, before the end of junior year -- before finals, if possible. Don't wait. Be among that first wave to ask.
How do I request recommendation letters without either coming off as pushy or like some sort of kiss-up?
That's the money question. I would suggest working off of a basic script like this:
"Do you feel like you could write me an outstanding letter of recommendation for my college applications this fall?"
The most important part of the whole thing is the superlative (look it up!) you use to describe the letter of rec. Think about it: you don't want anything less than the best that this potential recommender has to offer. Any ambivalence on the part of the person endorsing you will immediately let the wind out of your sails. A lukewarm letter, while not outrightly negative in itself, will create a strong contrast to the tone you're working to strike up through the rest of your application, and that can blemish (and effectively ruin) the picture you're trying so hard to paint.
If your prospective recommender hesitates or flatly uses the opportunity to beg out of the job, look somewhere else. Trust me. If, on the other hand, you get an unflinching yes, well, score one for you! Ask what you can do to make the job as easy as possible, and what sort of timeline they plan to work on so that you can follow up appropriately.
To recap, here are your next steps:
Identify your recommenders ASAP. (Not sure who or how many letters you'll need? Check out this handy guide.
Prepare your brag sheet (or junior questionnaire, as it's called at some high schools) with talking points about yourself. (Don't have a brag sheet at your school? Check out the questions that Santa Monica High School asks.
Build your personal rapport (without overdoing it) with your intended recommenders, and, before the end of junior year, ask if they'd be willing to write an EXCELLENT letter of recommendation for you for the fall.
Ask away! Be among the first students to ask for your recommenders’ time and careful thinking, and make sure that you’re ready to supply everything needed to make the job easy.