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bschool2014
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Thanks guys!

The problem is I'm not sure if my immediate manager will write a good reco. I sometimes get the feeling that she doesn't like me much.

The problem with the VP is he says "He doesn't know my weaknesses". Not sure what will hurt me more - an "incomplete" reco or a lukewarm reco.
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A lukewarm rec is much worse.

Given that information I would start the coaching process with the VP or just find someone else (in consulting at least there are so many dotted line supervisors i had many choices for my recs). But yeah as rgupta was saying you need to start the coaching process with your VP. Meet with him to go over the questions, provide some stories/examples to jumpstart his memory (if you need help getting stories go ask your peers, i'm sure they have plenty) and tell him the deadline is a week before it actually is to make sure he will submit something by the actual deadline.
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Always go with your direct supervisor (the person you report to)...they will provide a much more compelling case for you and the truth is they know much more about you. Top programs aren't swayed by the level of the recommender, unless you are a rising star and working directly for the CEO dont approach them for a rec.

Exceptions are if you get a president/former president, warren buffet, bill gates, or some other legend to write you a rec.
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River - My concern is whether my direct supervisor will write a good rec for me. Not sure what to do.
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River - My concern is whether my direct supervisor will write a good rec for me. Not sure what to do.
I had a similar concern about asking my direct supervisor for a recommendation. While our relationship isn't antagonistic, it's not particularly warm either. When I talked to her about being a recommender I specifically asked if she felt that she could write a positive and strong recommendation for me. She agreed to do so without any reservations. If you're worried about the recommendation than I would manage your supervisor very closely. Take your supervisor to lunch and outline the messaging you are trying to convey through your app and how their recommendation fits into it. I would make their job easy and give them detailed write ups of your "greatest hits" (situation, your actions, the results). Ask if they would be okay with you seeing the rec beforehand just to be sure the two of you are aligned.

I think your supervisor might surprise you. I've learned you don't have to have a warm relationship with your manager in order for them to support you 100%.
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Thanks everyone. I guess I'll go with my direct supervisor. I'll coach her as much as I can without sounding too annoying.
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I'd say go with your current boss, since most schools require that, and maybe "help" him remember some of your accomplishments and successes. If this is a matter of motivation, talk to him and explain how much it is important to you. Perhaps you should let him read one of your essays, and then have him talk about a specific experience mentioned in the essay, so he can make it look stronger by telling about it from his point of view.
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Let me take a different POV, and say that boss or VP, or CEO, what matters is not so much their position (as long as they can have something to write about you) but how EXCITED they would be. A lukewarm recommendation from ANYBODY is a terrible one. And you might search elsewhere for recommendations (For example, volunteer work from military experience, from religious/social involvement).

But if you are going with the workplace, think about this: Who would be more excited? If your boss doesn't like you, forget about it. with your VP, if he likes you, but isn't sure what to write, you can always offer to have a meeting with him to "remind him", bringing your reviews, showing him emails of praise etc. OR, you could work together with him (if he is amenable to it) to write a "sample draft" to help jog his memory allowing him to rewrite it as he sees fit.
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The problem with asking people from my extracurricular activities is I'm not sure if they can answer the questions asked by some schools. For instance, Kellogg has a specific question on career progression, Wharton asks specifically about how the applicant received critical feedback. Most of these questions can be best answered by a supervisor at work.

Work is the center piece of my MIT application. Not sure how obtaining a recommendation from an extracurricular activity would validate the things I say in my essays. I'm not sure how to resolve this issue. I've spent countless hours on essays and I don't want to get dinged because of recommendations.