Meaning of "Circle around with"

All too often my boss will say to me "I'll circle around with you later"

I assume it means "I'll catch up with you later" or something of the sort, but I feel the "circle" implies some sort of redundancy or endlessness loop of checking in on me. Is that right?

According to the BeeDictionary, "circle around" means to move around in a circular motion. That does imply redundancy or endlessness doesn't it?

In the case of your boss saying "with", it kinds of changes the meaning a bit. It implies that you are the one doing the circling around, and that the boss will join you in your circuit later on (hence, the "catch-up" meaning).

By "circling around" the boss doesn't mean endless or pointless wandering, but rather he means by what you do everyday, your normal tasks and jobs or errands etc. Thus, he would join you later in order to catch up with you.