Since I was applying to two schools, and both required two recommendations, I chose only two recommenders. I figured two recommendations for each wouldn't be too much of a burden!
Recommender A: The first obvious choice was my current boss. I've worked for him the whole time I've been at this company.
Pros: He got an MBA at a top ten school, so I knew he would understand the magnitude of what I was doing and be familiar with the importance of the recommendation to my application. He is also a good writer and is great about seeing the "big picture" in things. I wasn't too worried about whether he could translate my skills and performance into a recommendation for a top business school.
Cons: He is a bit of a procrastinator. Sure enough, he submitted Kellogg a few hours before the deadline (albeit before I did). Also, I don't do a whole lot of work directly for him: there are people under him that I do most of my work directly for, although I do meet with him weekly to go over things. So I was a little worried that he might not have enough in the way of specifics. Finally, I was worried about spilling the beans about my plans to go to school. But this worry dissolved in July before I started my application. I received a promotion (yay!) which meant that I would not be jeopardizing a chance to receive one after my plans were revealed. Also, when my boss told me about the promotion, he told me that management was discussing rotating me to another team to get some different experiences and exposure. This was also good news from the recommendation perspective, because it meant that my boss was likely going to "lose me" anyway soon.
Recommender B: For my second choice, I considered approaching another manager on my team that I've worked with extensively. But instead, I decided to approach a manager at my former consulting company.
Pros: I worked with him three separate times. We worked together really well and his reviews of my work were strong. We were also part of a team that was very social, so I can say that he knows me on a personal level probably more than anyone I've ever (or will ever) work for. I even went to his wedding! He is extremely articulate and I knew he could convey my strengths and weaknesses clearly and eloquently.
Cons: I hadn't worked for him in over 2 years, and we'd kept in touch but not extensively. Also, when I left the company, I was working for him at the time. I didn't think there were hard feelings, but I still worried there may have been. I also worried a bit about the fact that I was very friendly with him on a social level. Anyone who has worked in consulting has probably been on a project where everyone works hard and plays harder. Frankly, the man has seen me (and everyone else on that project team) drunk many times. Again, I didn't think it would, but I hoped this wouldn't cloud his ability to comment on my professional abilities. Finally, he had a new baby and both parents work, so I knew he was probably crazy busy.
I had read Your MBA Game Plan and liked the idea of putting together the "Game Plan" and sending it to the recommenders. I included details like: where I was applying, why, what I wanted to do with the MBA and why, and what I knew about each of the schools and what the adcoms look for in applicants. I felt this would help them say things like "Tinydancer plans to enter the pharmaceutical marketing field, and I believe she will be succesful because ..."
I decided to ask Recommender B first. I'm not sure why I didn't just call him in the first place, but I sent him a carefully worded email first, then waited. For two weeks ... nothing!! So of course I freaked out and convinced myself that he didn't want to do it and was blowing me off. My husband talked me down, and I called and left a message. He called back and said yes, he'd be happy to write me a recommendation, and sorry he hadn't seen the email (duh, I thought, he never read my emails when I worked for him either!). I sent him the details in an email and signed him up on both application sites so he could see the invitations. I also attached the old reviews he had written for me so he would have them handy, my game plan, my updated resume, and a sample recommendation and some recommendation tips from one of my books. Again ... for several weeks I heard nothing. I was worried, but I knew he was very busy. I called once and left a message to say I was just checking to see if he had any questions. About 3 or 4 weeks before the due date, I got notifications that he'd submitted. Phew. He also sent me (short) emails afterwards to confirm. The lack of communication concerned me a bit, but I knew that was probably just him and that it didn't mean anything about what he wrote.
I approached Recommender A a week or so after B. I was really nervous. It felt like the "I'm taking another job" conversation, but a little less bad since it was actually "I'm possibly leaving the company in a year and not for another job". I asked him to have lunch with me, and I'm sure he was ready for the "I'm taking another job" talk, so I think he was relieved when I told him what it was really about! He was really excited for me, really supportive, and best of all, told me he thought I had a great chance to get in. Now, if I were him I would have told me that even if I didn't think it, so I took that with a grain of salt! But I left the conversation feeling very comfortable with having asked him. As I said, he definitely procrastinated, but I wasn't afriad to remind him almost daily in the weeks before the apps were due and he didn't seem to mind. I sent him the same materials I send B, and he said it was really helpful and showed resourcefulness and commitment on my part (yay!)
So, for those of you that are mulling an application run in 2008, here is my advice on approaching the recommendations:
1) Consider how many of these your recommenders will have to write and how spread out the due dates are. I only applied to 2 schools and it seemed like plenty of work. Granted, the second is probably a lot easier since questions may be similar and they can cut and paste to a degree. But you may want to consider different recommenders for different schools so that you know they can devote the time required to write good ones. Or, potentially spread your applications between rounds so you can can spread things out for them. I did warn mine in the beginning that if I didn't get in to my top 2 choices, that I may apply to more schools in the 2nd round.
2) Put together something like the MBA Game Plan that your recommenders can reference to provide details related to your goals and what you like about each school. If you recommenders can say "Tinydancer will fit in well in Kellogg's team-oriented environment because ..." or "I am confident that Tinydancer will be a strong contributor to her Wharton learning team because ...", it will add a little something extra to your application and show that you have truly thought hard about your school choices and shared this information with your recommenders. Doing this also helps them understand your motivations for pursuing an MBA in the first place, which I think can make a big difference in the tone of their writing.
3) Choose recommenders that can really speak to specifics about your skills and abilities. Schools say that they don't want you to choose impressive names for your recommenders just to try to impress them. They say they can see right through this, and I believe them. If your recommender can only speak in generalities, you leave the adcom to draw no-so-good conclusions about your judgement, and perhaps determine that you didn't have anyone that could speak positively about you AND provide specific examples.
4) Luckily for me, my recommenders didn't ask me to write my recommendations. If yours do, I strongly suggest that you don't. Besides questions of ethics, the adcom is going to have a substantial writing sample for you in the form of your GMAT AWA and your essays. They are good at what they do and they will be able to tell if the same person wrote the recommendations. If your recommenders insist, I suggest that you compromise and write an outlined answer for each question with short phrases to suggest subject matter but leave the narrative to them. For example, for a question that asks how the applicant has shown leadership potential, write "ABC project and the way I pulled different groups together, Improvement of XYZ report for management, etc". If they still won't do it, get new recommenders. This is your application and only you will suffer the consequences if they can't devote the time to write a thoughtful document.
5) Give your recommenders plenty of time! 1 to 2 months should be plenty of time, but if you talk to them on the early side, be sure to check in every once in awhile to make sure it stays in the front of their minds. They are surely busy people and may forget when deadlines are, etc. A week or so before the deadlines, remind them again. Make yourself available in case they have questions.
6) Thank them appropriately. I sent B a gift basket ($50 value) and gave A a $50 gift card for a restaurant I know he likes. They will appreciate the gesture and they will remember it if you happen to decide to apply to more schools or need your boss's blessing to attend interviews or other MBA-related events.
7) Keep in touch. When you hear from schools, tell them! They will want to know and might be hurt if they aren't high on your list of people to inform, especially if the news is good. Afterall, they were probably instrumental in the results!