Welcome to Justanswer.com, my name is Dustin and I will do my best to assist you.
To get started, I need to know what version of outlook you are transferring from, and to.. Such as outlook 2011, 2016, etc?
Also, I need to know the version of mac osx you have on both macs, you can check as follows.
Click the apple sign at the top left of your screen, then click about this mac. And then where it says version, send that to me as a reply.
Dustin S.Senior Technician and Network Switching Systems Operator / Maintainer.