Jesus has already warned us of the poetic justice that awaits us if we make it a practice to judge others. "For in the way you judge, you will be judged; and by your standard of measure, it will be measured to you." If Jesus is trying to scare us with this talk, I'd say he's succeeded. But as soon as we start thinking we'll never ever want to speak to a brother about his sin again, Jesus gives us this instruction on how to confront someone properly.
I don't know how logs can get into people eyes, just as I don't know how camels can jump through eyes of needles or mountains can be picked up and thrown into the sea. Jesus likes to speak in hyperbole and maybe his audience found it humorous. In any case no one can see clearly with a log in his or her eye, certainly not clearly enough to see a speck in someone else's eye. Not only is it hypocritical to be pointing a finger at the other person, but you can't even see clearly enough to help them until you've taken care of yourself. So Jesus isn't utterly discouraging us from giving this kind of help to another person, he's just saying first things first.
I've often wondered how Jesus can be so sure that my problem is log-sized and the other person's problem is speck-sized. Is my sin always several million times greater than the other person's? I don't know if I buy that. But now I'm thinking that Jesus may not necessarily be making an objective statement about whose sin is greater, rather he is talking about a subjective assessment of personal sin. How should I view my own sin in comparison with someone else's? To me it is log-sized because it is my own. It stumbles me, it blinds me, it renders me incapable of helping the other person. For me it feels like a log while the other person's looks like a mere speck. Mine is the more pressing need of the two. It is the priority.
The trickiest part of the whole situation is that we tend to be most critical of people who commit the same sins we do. In other words, it is when the log in our own eye is the biggest that we think we see other people's specks most clearly. Hey, I recognize what's wrong with that person because I do the same thing! But, Jesus says, you have a log in your eye that is preventing you from seeing clearly. No, no, I do see clearly because I see how the other person is sinning! No, Jesus says, this is exactly when you are the most blind and the most prone to passing unrighteous judgment.
"Seeing clearly" couldn't just be about recognizing that someone else is sinning. We're all good at doing that. That's what makes us so judgmental. Jesus says we must "see clearly to take the speck out of your brother's eye," which means seeing clearly how to help him get out of his entanglement with sin. That kind of sight can only be acquired when we have learned how to deal with our own sin. Going through the whole humiliating process of trying and failing and stumbling around like a total loser, and after all is said and done we're still not sure we're completely free from the old ways. We've learned to distrust ourselves. Okay, now we're ready to help the other person, but this time it will be with a heart of sympathy and compassion, not a judgmentalism. It is that kind of sympathy and compassion, viewing that brother or sister not with condescending disdain but as an equal, that gives us the eyes we need to see clearly.