there seem to be many posts on this same issue. this fix to reset spotlight works well:
http://answers.microsoft.com/en-us/mac/forum/macoffice2011-macoutlook/when-i-search-for-messages-from-or-to-a-sender/39a3159e-b249-4753-8f09-6e7b4219a6e3however, after upgrading to 14.3.8 it keeps breaking to where i'm forced to do this routine over and over again - either option 1 or both 1 & 2. it just doesn't hold.
another thread on this topic:
http://answers.microsoft.com/en-us/mac/forum/macoffice2011-macoutlook/outlook-2011-and-spotlight-search-not-working/197645ed-4a02-4cbe-b057-896e9742cf4a?rtAction=1384325266429
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