One of the best resources for pastors I have found is the book Care of Souls in the Classic Tradition by Thomas C. Oden which is available free online. Here is an excerpt from chapter four that gives practical wisdom regarding pastoring people toward forgiveness.

The Actively Guilty and the Passively Guilty

Those feeling guilt over willed misdeeds are treated differently than those who project fantasies of guilt beyond their willing. This important pastoral distinction is difficult to make and needs a general rule to guide its application. For those grieving over real guilt for actual misdeeds, Gregory hypothesizes that three stages are required for a return to moral health — penitence, pardon, and reparation. The pastoral intention must be to help keep the remorse or regret in due proportion to the values that have actually been negated.

It is appropriate that persons should first experience remorse and the struggle of conscience over unjust actions. The pastor must not try to protect persons from the witness of their own conscience and from going through a reasonable period of keen awareness of lost values.²⁵ During this process it is fitting that these losses should be felt before God and in the presence of God’s holiness. The prototype of the penitential prayer is Psalm 51: “For I know my transgressions, and my sin is ever before me. Against thee, thee only, have I sinned” (vv. 3, 4, RSV). Pastoral listening cannot cheaply reduce the pain of standing before God in the remembrance of these losses.

But pastoral care does not end with moral sympathy; it continues, in the second place, with the proclamation of forgiveness, for the next pivotal movement of consciousness is the acceptance of divine pardon. Pastoral care, when effective, brings one articulately, clearly, and directly into the presence of divine mercy. The pastor must learn how to use human speech to declare the divine address. The aim is to assist the hearer in trusting God’s forgiving Word and resting serenely in it. The parishioner who cannot meaningfully experience this deep dimension of forgiveness may fall into a habit that Gregory calls “immoderate affliction”²⁶ — forever overemphasizing one’s deficits, always being too hard on oneself, seemingly making it impossible for God to forgive.

Pastoral care of the guilty proceeds, however, with still a third step that is not to be taken lightly — an appropriate act of reparation for wrongs done. Having once rested confidently in God’s forgiveness, a new danger lurks, namely, that one will too readily assume that God will always forgive. This might tend to reinforce the temptation to do the same things over again, or worse. It would be to use God’s pardon as an excuse for sinful self-assertion, turning God’s unmerited mercy into “baneful reassurance.”²⁷

Yet every pastor knows that some people are inordinately burdened with guilt feelings. When these guilt feelings are carefully examined, they focus upon nothing that the individual has actually done but upon diffuse social guilt or felt corporate guilt, based on actions that were partially or wholly out of one’s own hands. In some cases guilt adheres only to fantasized misdeeds that have been mentally conceived or imaginatively projected. Guilt in some cases is directed only to something one has thought of doing yet not actually done. Gregory would carefully guide such persons through a discriminating act of self-examination in order to sort out the degree of their own willingness to consent to a harmful deed. This exercise centers upon ascertaining the extent to which one would have given free consent to an overtly evil act had one been given full opportunity.

This self-examination is based on a clearly delineated psychology of will that Gregory had learned from earlier church fathers (Tertullian, Jerome, Augustine) but had himself developed and refined.²⁸ According to this psychology, the dynamics of guilt and self-alienation occur in three distinguishable stages, analogous to the fall of Adam. Stage one: A suggestion of sin is made. Stage two: one then thinks about the imagined pleasure that would accompany the misdeed. Stage three: one freely consents — one wills to do it. Even if one wills to punch a neighbor in the nose, however, one may still have to wait for the opportunity. Hence the crucial determination as to whether one has actually consented, stage three, may require deliberate and detailed self-examination.²⁹

The psychological dynamics of this examination are further complicated by the fact that any of these three stages may be further enmeshed in a triadic collusion between (1) our flesh, which is already prone to sin, (2) a superpersonal demonic power, “the enemy,” and (3) our own will, fully determined by us. In the last analysis it is only our will or spirit that can consent. Therefore only the will can sin. The body or flesh in itself has neither freedom or consent. By suggestion and temptation the demonic forces, Gregory hypothesized, were incessantly trying to lure the human will away from God. The flesh anticipates the imagined pleasure that might accompany a misdeed. Yet that in itself is not sin but only its precondition. At that point one may or may not give consent. It is the actual consent for which one is duly responsible. Parishioners are asked carefully to examine into which of these degrees of complicity they have fallen. The first and second degrees of complicity may carry some level of culpability, but finally one can sin only with one’s own will. The psychological principle: the further one has actually gone toward freely willing a misdeed, the greater is the need for penitence, pardon, reparation, and reconciliation with God and neighbor.³⁰

However far toward willing consent one may have gone, pastoral guidance nevertheless wishes to show that the divine pardon is immediately available to the truly penitent. The one who earnestly and actively prays for reconciliation can be confident that forgiveness is immediate and not delayed.³¹

Feigned Penitence and Penance Without Restitution

Feigned penitent acts are in vain if they do not manifest themselves in seriously attempted behavioral changes. Bathing in tears does not suffice. Gregory employs the devastating analogy of a sow who, taking “a bath in its muddy wallow. . . makes itself even filthier.”³² Those who pretend to be trying to change their behavior while pleading with God for forgiveness yet go right back to the muddy wallow are opening themselves up to an even greater deception — the mocking of God’s pardon. The purpose of washing is to become clean. You may as well not take a bath in the first place if you intend immediately to plunge back into the mud. That amounts to thumbing one’s nose at divine mercy.

Suppose you are called into court and plead with the judge for pardon. You gain the pardon, walk right out of the court room, and blatantly do again precisely the wrong for which you had previously asked to be pardoned. Does that not show contempt of the judge?³³ It is no easy matter to change such a steady disposition for evil. Those who are by strong predisposition morally evil “are moved in vain by compunction to righteousness, just as, for the most part, good are tempted to sin without harm.”³⁴

The pastor will meet those parishioners who will “Do some part of a good deed without completing it,” yet remain unduly confident that they have in fact done it already, and only when they will find the regrettable side of their intention manifesting itself, will they become naively surprised. Paul grasped the dynamics of this inner dividedness in this memorable way: “In my inmost self I delight in the law of God, but I perceive that there is in my bodily parts a different law, fighting against the law which my reason approves and makes me a prisoner under the law that is in my members, the law of sin” (Rom. 7:22ff.). On this assumption, the pastor does well to examine not only the initial expression of regret over guilt, but beyond that whatever long-term behavior patterns may follow after it. Gregory’s analysis is largely consistent with modern behavior modification theory and behavior therapy that focuses on actual, regularized, visible, even measurable, behavior change more than the hidden mysteries of supposed intentionality.³⁵

Is reparation required? Gregory takes the case of a parishioner who, let us suppose, having at one point grossly sinned, has now completely desisted from that sin and yet does not wish to go through any semblance of an awkward or embarrassing act of penitence before God for past misdeeds. Inwardly the person is saying, “I’m not trapped there any more. Why do I need to repent?”

Gregory answers with three amusing analogies: a bad poem, an unpaid debt, and an unretrieved insult.³⁶ Suppose I write a very bad poem and then decide to give up writing. That does not efface what I have written just because I am not adding anything to it.

Suppose a person has gotten deeply into debt, but now has decided that he is not going to incur any more debts. That does not mean that all previous debts have been paid off. It simply means that no new debts are being incurred. The debtor still needs to pay off those old debts.

Suppose I insult you and then I say, “I am not going to insult you anymore.” My being quiet does not make reparation for the earlier insult. I must go further than that.

Similarly, if it is God before whom we stand, “we certainly do not make reparation merely by ceasing from evil.”³⁷ A further active step is needed — from penitence and pardon to the new life that emerges from it. One does not just undergo baptism and then do nothing, for baptism rehearses not only the death of an old life but also the rising to a new life.³⁸

Those who frequently commit small misdeeds are to be counseled in a different way than those who sink into a grave sin only once in their life or very rarely. Frequent irresponsibilities are compared to tiny rain drops: if you get enough of them, they can cause a flood. It is something like a bee sting: one sting does not hurt much, but a thousand can destroy life as completely as a single rapier thrust to the heart. If bilge water is slowly and inconspicuously rising in a ship, and no one notices its continued rising, it has the same devastating effect as if a hurricane threw the ship on the rocks and dashed it to pieces. Thus, if you neglect these small incremental matters of behavioral deficit and minor excess, you may in time be lured into larger self-deceptions and collusions that will spell disaster.

This is the precise problem of the small misdeed — it fosters a lack of concern. One becomes inured to its consequences. One imagines that it is nothing at all. It is powerful only because it is small. Pastoral counsel will try to unpack the correlation between the raindrop and the impending flood, the bee sting and the death, the slowly rising water and the potential disaster.³⁹

On the other side of the fence there is the individual who lives a solemnly upright life, whose small sins are carefully monitored, yet who suddenly finds himself in the midst of an unexpectedly grave sin. The prototype of this behavioral pattern is the legalist of whom Jesus wryly spoke, who filters his wine to get rid of a gnat, but then gulps down a camel (Matt. 23:24). Such persons discern trifles. They are clear about where the tiniest deficits lie. They tithe mint and cumin, the least of all of the herbs, yet forget the weightier matters of law, judgment, and mercy — and faith (Matt. 23:23). Overattentiveness to the small misdeed may contribute to the neglect of the large. To this is added pride, conceit, and a lethargy that comes from spiritual elation, an ecstatic awareness that assumes: “Aren’t we wonderful!”