Q: I used time machine to transfer data from one macbook pro to a new macbook pro. Spotlight search will not work on Microsoft Outlook on the new Mac. Anyone else have this issue? I have tried everything and nothing seems to activate the search.

You may have to update your version of Outlook for Spotlight to work with the newer operating system.

That's a question to ask Microsoft.   I would also add, make sure you have completed an entire hard disk index of your hard disk after the install.     To do so, add the drive to the Privacy in Apple menu -> System Preferences -> Spotlight Privacy, and then remove it, and make sure the entire drive is designated as searchable.  It may take overnight for the index to take place.  The Spotlight menu will stop indicating that it is indexing when it is complete.