We live in a world where many know Jesus’ teachings against judging others but forget why He teaches it: He does not say we cannot or must not, but rather we ought not and for good reason.
We will be judged, and the experience of our own judgement will hinge on how we have judged others. Thus, it is better not to judge anyone at all. But we cannot help judging; we are constantly evaluating, discerning, seeking to understand. Jesus is not warning against that kind of judgement; rather He is warning more against the part of judgement we dislike.
Sentencing. Condemning.
We are always going to judge, but it is our conclusions that endanger our souls and where we most often fail in charity. It is in the sentencing, is it not, where we desire mercy? Yet it is there where we often refuse it when judging others: we draw conclusions, make assumptions, and execute complete strangers in front of the hangman of our own ego, not realizing we are often just as condemnable. For our eyes are clouded by sin, by ignorance, cataracted by the beams of our own pride. But the scrutiny of God is not so impeded; in 1 Samuel 16 the prophet Samuel is sent to anoint the next king of Israel, and he sizes up the sons of Jesse, settling upon Eliab. But God says to Samuel, “Do not judge from his appearances or from his lofty stature, because I have rejected him. God does not see as a mortal, who sees the appearance. The Lord looks into the heart,” (verse 7).
Therefore, since we cannot look into the hearts of others, we must judge with charity from our own, giving the other the benefit of the doubt, showing even our enemies the “condemnation” we ourselves hope to receive from our ultimate Judge. For it is far, far better to err on the side of charity and find that we were too merciful, than to err on the side of arrogance or pride, and find that we failed to love, for “…the measure with which you measure will in return be measured out to you,” (Luke 6:38).