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thistime
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There are a number of opinions on when to take your first simulated test.
here is what I did and it seemed to work, but this is definitely not the only way:

I took a practice test (PowerPrep or GMATPrep) - yes I "wasted" it but I was able to get my position at the beginning of the prep. Having a starting point, and a goal, I was able to put together a strategy/study plan to achieve my goal. Keep in mind that i scored 540 on my powerprep, so I definitely needed a lot of help. I thought that was a better strategy than assume I was good in something, which I was not and then I used my weaknesses to improve. It gave me a realistic picture and a necessary motivation to kick my behind. On the other hand, you could also take any similar CAT test and get a clear picture and save your GMAT Prep for the last month to hone your strategy and evaluate final result with close accuracy - any GMAT book you buy these days has a test in it.

Another strategy is to take a GMAT Prep test in the middle of your prep - take the verbal portion only for example after you are done with verbal to get an understanding of your position - I think that's also extremely helpful too but any practice test from Kaplan, PR, or MGMAT could do that for you. Of course GMAT Prep would give the most accurate results.

P.S. Official Guide is not very hard by the way, so don't be fooled.
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