Pontificator has a great quote by Cardinal John Henry Newman to spur a discussion on confession, which I hope you will be part of if you care to (by clicking on the headline, above).
I will say this: as in all matters, sometimes people fall into extremes.
At one extreme are those who are painfully scrupulous and all I can say is my heart goes out to them. It takes more wisdom and experience as a priest to know really how to lift the burden they carry, because sometimes, it seems nothing I as a priest say in the sacrament does any good, other than absolution. One of the basic problems I perceive with scrupulosity is an inability to trust, or perhaps to submit to, Christ.
At the other extreme are those who are awfully general. The wisdom that underlies the practice of this sacrament is that our lives are lived in the concrete: it is in concrete, specific acts and choices that we pursue holiness or damnation, as we gradually become whoever we will be for eternity. Thus, we need to examine the specific choices of our lives, in order to discover the real direction of our lives -- either Godward or selfward.
Interacting in the sacrament with folks who confess rather generally is a delicate matter, because I am not entitled to assume they haven't made a good self-examination, and asking specific questions say, about the various commandments, is extremely delicate. I really don't want "to go fishing," nor do I want to imply any sort of accusation.
A third concern, not lying at the extremes, are those of whom I wonder, are they looking at the bigger picture?
There is, in moral theology, a school of thought called "the fundamental option" which, while having a problematic aspect, nonetheless has a good insight: that we tend to have a fundamental orientation of our lives, that is shaped, statue-like, by particular choices over time. (The problematic area of "fundamental option" theory is exactly how to understand the moral significance of individual actions.)
I frequently invite a penitent to ask the question, what is the larger direction of my life? What resolution might God be calling me to?
Sometimes, my counsel to a penitent is along these lines: "It may be that the Lord has moved you toward some resolution; perhaps its half-formed in your heart right now. I don't need to know anything about that, but I would strongly encourage you to take advantage of this moment of conversion, and ask the Lord what he may have in mind" and I send them to spend some time before the Blessed Sacrament--and perhaps ask him for the courage to commit to that resolution, if they feel so inspired.
I also like to invite people to reflect on the wonderful fact that they are in confession, particularly when they seem downcast: "the very fact you are here at this moment is absolutely certain proof that God loves you; for it was he who stirred up in you any desire to come here; if 'circumstances' seem to have brought you here, know that God made that happen! And why would God bring you to this moment of grace unless he loved you?"
Many people have certain priests who they like as confessors; my own feeling is that, while I admit there are some priests who I'd rather not go to confession to--purely because of my own relationship with them--generally, any priest will do for me. If my own pride or any other reluctance is at work, I have no compunction about confessing anonymously (and neither should you, although there are times I wish I could see the person on the other side of the curtain--it would help me understand the person's situation better).
I sometimes wonder what folks think of the penances they accept from me. I try to match a penance to the situation shared; but too often, I receive no inspiration, and I resort to something rather standard. I have to remind myself: I'm a priest--Christ is present in my ministry, and I know that's true when I give absolution. That does not mean, however, that I have been given any special, supernatural gift of being a doctor of souls, as it seems some priests have been given. One point I make about the penance is that is not a "punishment" nor even a "payment," but rather more like an "offering" and even more, healing. One penance I often give--which draws a puzzled reaction--is to ask a married person, "can you do something romantic with your spouse?" I could be wrong, especially as I haven't been married, but I stand by that as a worthwhile penance: because what I'm intending is that the spouse I'm speaking to take the lead in some healing within that very important sacramental relationship of marriage.
Perhaps it seems frivolous to some, but taking your spouse out to dinner, treating him or her as king or queen for a day, bringing flowers home, sweeping your wife off her feet, or, simply, making love! are all very wholesome and, ultimately, if done with the right intention, holy acts. (I am tempted simply to say, "make love to your wife or husband," but I feel sure that would embarrass many, so I refrain, and hope my more general comment that "doing something romantic" could be anything, as long as its an act of love.)
This gives me occasion to remind you, dear reader, that when you go to confession, the priest does not, merely, assign a penance; the penitent must accept it. At least, so I was taught and so is my practice. After suggesting a penance, I ask: "can you do that?" and/or, "that's not too hard?" Sometimes, people will give a reason they can't do a penance (e.g., I might say, "can you apologize to that person?" and the penitent might reply, "I don't know that I'll see him again."), and I will change it.
As a confessor, I try to remind myself how delicate, how privileged, this moment is. I recall something a priest I know says often at penance services for high school children: pray for us priests that we won't get in the way of Jesus. There are times I wonder if I should say anything at all, and there are times I merely suggest a penance and give absolution.
Finally, I know some folks wonder what the priest will think of them, and this holds them back. In addition to reminding such folks that, first, they can approach any priest, and second, they can confess anonymously, I would say this: all the parishioners I deal with, outside the confessional give me more than enough opportunities to "think about them" (i.e., think about their foibles or sins) if that's what I want to do--which I don't! When I get a quiet moment, the very last thing I want to do is think, "My goodness, I can't believe Joe does such-and-such!"
As C.S. Lewis pointed out in his brilliant Screwtape Letters, sin is boring.