lets not forget what GMAT really is: it is a statistical predictor of success in first year graduate business school. no more. no less. it has nothing to do with IQ, and it is not directly measure any of your abilities.
according to GMAC the standard error of your result is 29 points. which means that in about 1/3 of the cases you can get up to 29 points more than your actual statistical predictor grade, and in 1/3 of the cases you may get up to 29 points less than your "real ability". therefore, in my view any improvement of 50 points or less has little meaning (statistically).
according to GMAC, retaking the test should not affect your score statistically. i.e. you would get grades that are in the area of your real ability with respect to the standard error of this estimator.
given this, if i were an adcom i'd look at the average of the test scores, regardless of their number.
however there is one thing that GMAC has overlooked: people do get better, people can learn new stuff and improve their skillls. they may do it by studying to the gmat (most of us would admit that they did learn som new math principles when studying to gmat) or they may do it by studying something else.
in fact, since GMAT is a good predictor of success in Bschool... the best way to improve your score is to study skills that improve your chances of success.... the GMAT test will probably reflect that somehow. this is probably why, in my opinion, adcoms do, in fact, looking at the maximum score.
and one other thing....
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Most (caveat: not all) super IQ 780 GMAT types make good engineers and spreadsheet monkeys, not dynamic determined business leaders. If there is one thing that characterises self made millionaires it is incredible drive and ambition. The kind of drive that forces people to spend a year improving their GMAT score from 450 to 700. If I were to pick a wingman for a future business startup, I would pick someone with this drive every time.
while i agree that drive, determination and ambition are very important traits of a business leader, choosing the right targets to "use" those is even more important. in my view spending a year to improve your GMAT directly (i.e. not by improving your general skills) is not choosing the target wisely. it shows, in my view, lack of perspective. i don't mean that you shouldn't try to improve it if you need to.... but i wouldn't spend a year doing so, and saying this is my main target. also.... self awareness is another personal trait which is needed by leaders. when you take the GMAT you probably roughly know what your score would be. you can avoid taking it if you think you are not prepared enough. retaking GMAT again and again might be interpreted as lack of that self-awareness. this is probably true, as pelihu noted, when you retake more than 3-4 times.