Goldfinger
Thanks very much for giving me insighful picture. No worries/
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1) I think , the admissions process is not such a simple ball game, which can be standardized so easily. You GMAT score is just a component in this puzzle. Its not an ends in itself.
2) Secondly if have a Part time Diplona from IIM Calcutta, use it. You have invested your time outside work to study. Whether you have used it in your job currently or not is secondary. Your motivation to study at ur own time atleast comes out when you show this. Your essays are independent of your academic profile and what you chose to delibirate on is your prerogative.
3) This is Jan 2011 intake forum, the admissions to which are now closed. Your query here isnt the right place. It should be placed in a fresh discussion or in Sep 2011 intake if you plan to apply in Sep 2011.
4) Well INSEAD cares about international work experience, but if you dont have it its not an ends . I have come across students who dont have such an experience but still make it to European Business Schools , LBS or INSEAD. If you have worked with international customers even in India , you should have gained experience. And if you havent dont that.. Dont let that discourage you. I doubt INSEAD has ever said categorically that it wont admit you if you dont have x years of international experience.
5) What schools you should apply to depends on what you want to do, and what your professional and academic profile is? Whether you want to be in a one year or 2 year program. Whether you want to remain focussed on Finance, or GM, or Entrepreurship or Operations. Its an open ended question and no one can give you a specific answer here. Someone who gives u an answer really doesnt know it himself

Finally my only advice to you focus on your GMAT first. Dont have too many things to do at once. Take it one step at a time. Get done with your GMAT, focus on your recos, and essays. And then look at the interview if you get shortlisted.