"I will make his countenance friendly by the gift which goes before me, and afterward I will see his face: perhaps he will accept me." Targum Pseudo-Jonathan preserves Jacob's private calculation in Genesis 32:21, and the Hebrew wordplay underneath it is one of the richest in the whole book.
The text uses the word panim — face — four times in rapid succession. I will appease his face with the gift that goes before my face, then I will see his face, perhaps he will lift up my face. Four faces. Esau's, Jacob's, the gift's, and in some readings, God's.
Why faces?
The rabbis taught that reconciliation happens face to face, never side to side. But before the faces can meet honestly, something has to precede them — some softening, some sign of good will. Jacob sends the gift as his proxy, his first face, so that when his actual face finally appears, his brother is ready to see it.
There is humility here too. Jacob does not say, "He will accept me." He says, perhaps he will accept me. The reconciler holds the outcome loosely. You prepare the ground; you do not demand the harvest.
The takeaway: before the hard conversation, send something ahead that says, I come in peace. The face will follow the gift.