1. Choose the right time. You want to ask any of your recommenders for a letter of recommendation (LOR) at least six weeks before it is due. This gives your supervisor enough time to pump the letter out as well as for you to give him or her several gentle reminders. You DO NOT want to be running around chasing your recommenders on the day of the deadline. In addition to giving your boss enough time to write the letter, you want to ask at the right time. A great time to ask for a letter of recommendation is at the wrap up of a project or initiative in which you’ve played a helpful part. Another good time is at the end of a positive performance evaluation session. In both of these instances, you know that your boss has positive feelings about you and your work. Try not to ask for a letter of recommendation during the middle of a crazy-hectic project or in the middle of any kind of disappointing initiative in which you’ve played some part.
2. Frame it well.
Your going to graduate school full-time means your boss is going to lose a talented member of his or her team. This is always going to be at least a bit annoying to managers. However, you can frame your request to both compliment your boss, your company, and to remind them of your goals. Here is an example:
During my time here at x company working under your management, I have grown a lot professionally and become even clearer on my personal and professional goals. One important step in my journey is to get my MBA so I can expand my skills and have the experience of spending two years full time learning and living with my peers. I would really appreciate it if you could serve as a recommender for my MBA applications. I have already created a recommendation package for you that includes my resume, some details on the programs I am applying to, and a few of my essays for your reference. Do you think you can enthusiastically recommend me for graduate study?
3. Be prepared for your boss’ reaction.
If your boss seems very surprised or hesitant, you want to give them time to think it over (and give yourself time to reconsider if you really want him or her as a recommender). If your boss’ reaction is less than ideal, you can say:
I know you have a lot going on right now, so if you need a few days to think about it, that’s fine too. It would be great if you could let me know by the end of this week, so that I can ask someone else if necessary. I am so grateful for my job here, and I don’t want you to take my wanting to go to graduate school as my being unhappy here. I’m just very excited about getting more education so I can be an even better leader.
Hopefully, your boss will respond enthusiastically, after which you can give him or her your recommendation package and scratch that task off your list.