How detailed does a confession of sin have to be? Do you need to list out all that you've done wrong?
First, we need to remind ourselves what is the purpose of confession. Confessing our sins means we are facing up to the fact that we were in the wrong and we are no longer going to hide that fact. Confession is first and foremost to God. "If we say that we have no sin, we deceive ourselves, and the truth is not in us. If we confess our sins, He is faithful and just to forgive us our sins and to cleanse us from all unrighteousness" (I John 1:8-9). This sets the principle: if we want forgiveness of our sins we need to admit that we were wrong to the one we have wronged. Therefore, when a Christian wrongs someone, a part of settling the matter is for the Christian to admit that what he did was wrong to the one he harmed. All sin is against God, so all sin needs to be confessed to God. When we harm another person and seek their forgiveness, we must be willing to admit that what we did to that person was wrong.
In the parable of the prodigal son, we are told that "he squandered his estate with loose living" (Luke 15:13). He comes to his senses and returns to his father, confessing his sins. "And the son said to him, 'Father, I have sinned against heaven and in your sight; I am no longer worthy to be called your son'" (Luke 15:21). The son admitted that he had sinned against God and his father, but notice that the confession did not spell out what he had done. Nor was it necessary. It was enough for his father to know that he knew what he did was wrong. His father immediately welcomed him back.
I should balance this out. I have some who "confess" by saying, "If I committed any wrong, ..." This is not facing up to what you have done; this is hedging. A person saying this doesn't believe he did wrong, but he knows others think he had done wrong. He wants the problem to go away, but he doesn't want to admit to something that he feels he didn't do, so he hedges. He is much like Judah of old, "Judah has not turned to Me with her whole heart, but in pretense" (Jeremiah 3:10). Nothing has changed. If the person had sinned, he remains unrepentant in that sin. If the person had not sinned, he left a brother thinking he had sinned just to get the issued dropped. True confession is stating that you were in the wrong.
Christians are encouraged to solicit help on their behalf. "Confess your trespasses to one another, and pray for one another, that you may be healed. The effective, fervent prayer of a righteous man avails much" (James 5:16). There are going to be times when the gravity of your sin is going to make you feel unworthy to approach the Father of All to ask for forgiveness. It is proper to ask your brethren for aid in pleading your case before the Almighty.
Unfortunately, many have formalized this practice beyond what is mentioned in James. There is nothing in this passage about going before a church to admit your sins. Nor is there any indication that every sin must be mentioned by name. I know many people who have committed grievous sins, who talked to me in detail about what happened and why. They needed someone to share the burden with and someone who could direct them in repairing the damage that they have done. This is the type of confession that James was talking about. But it remains a private matter because the person had turned away from their sins, repented, and desires forgiveness. Love demands that the damage already done be minimized as much as possible.
"Brethren, if anyone among you wanders from the truth, and someone turns him back, let him know that he who turns a sinner from the error of his way will save a soul from death and cover a multitude of sins" (James 5:16).
The idea of covering sin is not one of hiding the fact that sin occurred but burying the details of a repented sin. There is shame associated with sinning, and we ought to be sensitive to sparing a repentant brother of that shame. Concerned brethren ought to be thinking about rebuilding a brother's reputation, not dragging his guilt out into the limelight.
This often annoys some in congregations. They don't feel a sin has been dealt with until they were told all the specifics. Yet, this is the foundation of gossip -- wanting to know the bad in others so that you can feel better about yourself. Upon what passage can one go to state that every person in a congregation needs to know about every sin? Or when a person has sinned publicly and states "I've sinned," upon what passage do we look to say that he must state before all a list of his sins?
One preacher gave a good illustration of this:
"A few years ago, during a congregational assembly, an elderly sister in Christ who was senile in some regards became upset at the elders because of a doctrinal, yet expedient decision, they had made. She, in front of all who were present (those who were present made up about 45% of the entire congregation), told them (unjustly) that they should resign. When it was my turn to speak, I kindly but firmly rebuked her in front of everyone. As soon as the meeting was over, she immediately came up to me and apologized, and then went to each of the elders and apologized. They accepted her apology. However, a few weeks later, I found out that there was a brother (a sound, good man) who was there who demanded that she come before the entire congregation and confess her sin. He said, "This was a public sin, and the Bible says, 'As public the sin is, that's how public the confession should be.'"
What happened? Well, the sister did give me a letter to read before the entire congregation, but at the same time it dragged out, to the chagrin of her and her family and the elders, something that, as far as Scripture is concerned, was resolved the moment she penitently confessed her fault to her God and to the ones she had wronged. There was no scriptural need for her to go in front of the entire congregation, and saying that there was (a common belief in the church today) is erroneous and adding to God's Word."
If the brother in this example was concerned that the matter was not resolved, he should have gone to the sister directly. He would have learned that she had repented and apologized to those involved. Then the matter would have been properly dropped. Instead, a repented and forgiven sin was repeatedly recalled because third parties, not involved in the problem, felt they had to be involved.
In all that we do, the aim is to get a sinner out of his sins and back on the track of righteousness. To do that, a sinner must confess his faults to God, repent of his sinful ways, and walk the proper path once again -- that gains his forgiveness for his sins. When a person harms another, he confesses his fault to that person, repents of his sinful way, and walks the road of righteousness with his brother once again.
What about someone who has sinned such that "everyone" knows about it? Ask yourself, do you know that he admitted he was wrong, even if you don't know the details? Do you know that he has changed his ways? Then what more is needed, seeing that he didn't harm you? If you don't know that he has changed, then go talk to that brother because the most important thing is making sure he is back on the road to heaven. What a public confession simply does is get the word out quickly that a person has left his sins behind. It is not required; it can be handled by talking to people one-on-one or in small groups as the issue arises.