Christian doctrine teaches that we are completely and totally saturated with sin, and Jesus' teachings on judging reflect extreme ignorance of our own sinfulness. The gospel is the antidote to judging, and it's what Jesus brought to those who were condemned. When we understand the gospel, our faults shouldn't surprise us, and we should be more embarrassed by our own sin than enraged at others'. Judging is not about assessing someone's position, but rather dismissing them as a person. We should speak with grace and truth, just like Jesus did, and be sensitive to what people can handle. We should also learn to listen before speaking, and be patient with the pace of God in someone's life.
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