Listen to what Paul, the apostle writes about winning. His definition differs greatly from ours.
20 To the Jews I became as a Jew, so that I might win Jews; to those who are under the Law, as under the Law though not being myself under the Law, so that I might win those who are under the Law; 21 to those who are without law, as without law, though not being without the law of God but under the law of Christ, so that I might win those who are without law. 22 To the weak I became weak, that I might win the weak; I have become all things to all men, so that I may by all means save some.
- I Corinthians 9:20-22 (NASB)
For Paul, winning never pertained to things. For Paul, winning pertained to people. The apostle desired to win people to Christ. How did he try to win people? Paul won people by being winsome.
Winsome is a word seldom heard these days. It means “to be winning”. Winsomeness is the art of engaging people to find a point of common connection and compatibility. Through connection, one person may begin understanding the thinking of another.
I believe Christians need to be winsome. We need to engage the world in an understanding fashion in order to build a connection with people. Winsomeness requires loving another person; caring for him or her. Jesus came to seek and to save lost people, not to gain stuff. This is why He hung around prostitutes and tax collectors. Believers should do likewise.
 Prostitutes and tax collectors were the scum of the earth in Jesus’ day.