Cunningness vs. Observation - How to Exercise Judgement Without Being "Judgemental"

"Judge not, that you be not judged." — It is probably one of the most quoted and most misunderstood passages in Holy Scripture. We are warned not to nitpick people and presume to judge their hearts, lest we fall into condemnation ourselves. Yet, at the same time, Scripture repeatedly instructs us to use discernment, to test everything, and to "judge with righteous judgement". — So what is the difference?

What is the difference between wise discernment, and hypocritical judgement? When are we faithfully inspecting a person's actions, and when are we just being cunning?

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According to the words of Jesus Christ, the Son of God himself, it is possible — in fact, it is desirable — for us to identify false prophets, wolves in sheep’s clothing, by looking at their actions.

From a distance, you may not be able to tell. It may be a very convincing sheep costume. Indeed, it’s probably a real sheep which the wolf himself has slaughtered and skinned, so that from a distance when you look, you see real wool, the real features of a real sheep.

But like every other sin that is handed to us by the devil, Satan is most unoriginal. He is able to invent nothing. All he can do is take the good things which God has created, and he twists them. He cannot invent any new, or unique pleasure. He simply takes the good of marriage, and he twists it and perverts it into lust, and fornication, and adultery. He takes the good desire to enjoy the good gifts of God as the reward for faithful labor, and he twists that into a desire to posses those things though theft. Think of any sin, and it is a sin which began has something good, and which Satan has twisted so that we pursue it in the wrong way, or at the wrong time, or for the wrong motive. This is no different.

We are told by Jesus himself that it is possible to look at a person's words, to look at a person's actions, and to determine that they are in fact a wolf in sheep’s clothing. I spoke of the wolf among the sheep, the wolf that is wearing a very convincing sheep costume. From a distance, you can tell no difference between him and the sheep. The look is the same, and the wool is the same, but look just a little closer: 

Walk into the field with them and see what they are eating. When you look closely at the mouth of a real sheep, you see grass stains. But when you look closely at the mouth of the wolf, you see it is stained with blood.

“By their fruits you shall know them.”

It is good that we are able to look at the actions of the wolves, and identify them as wolves. But even this good gift from God — this ability to identify — is something which the devil twists into a most insidious and dangerous sin.


One of the vices Saint John of the Ladder warns us about is the sin of cunningness. In a book I read a while back, the author elaborates on this particular sin:

A cunning person makes false conjectures and projections, and fantasizes he that he understands the thoughts of others on the basis of what they say. Cunning persons try on the basis of external signs to presume to know the secrets of people’s heart. I hear people say, “Such a person dislikes me,” and I ask, “How do you know?” “From the expression of her face,” is a typical answer.

There are many examples of cunningness that he gives:

He sold a certain plot of land to deal with some debts that the church had. Rumors started, and he heard from somebody, “I know the real reason you sold that land. You’re just wanting to use that money so you can grease the wheels and become archbishop. You just want more power.”

This particular man, having spent a lot of time on Mount Athos, had become accustomed to giving a particular blessing in which the priest simply says, “May God forgive you.” He gave that blessing to a particular person in this church, and she was in tears later, so distraught that he thought she was just some poor common woman who needed God’s forgiveness.

He was giving communion to a large number of people. And this one particular man, he gave him the Eucharist, and he just didn’t mention the man’s name when he gave him the Eucharist — a simple oversight, no ill will, no ill intent — It turned out this man was just tortured for the rest of that day. He told somebody else that obviously this priest just thought of him as a nameless nobody.

Someone says,

  • "I just don’t like that look that you gave me."
  • "I don’t like that look on your face."
  • "I know what you’re thinking."
  • "Obviously you’re judging me, ’cause I can tell by your look."
  • "Obviously you don’t like me; I can tell by the look on your face."

You see a look on somebody’s face, and you presume that you know exactly what they are thinking. A person might just have a headache. A person might have a stomachache. A person might be thinking of something painful that has nothing to do with you. It could be that you walk up and spend time with a particular person, and no sooner do you get there, but that person is in a hurry to leave, and they get out of there. And so you say, “Ah, obviously he doesn’t like me. If he liked me, he wouldn’t have left in such a hurry,” not realizing that he simply was running late for an appointment.

You offer to help somebody with some errands that they are running, and they graciously turn you down. And you say, “Now there’s proof that they don’t like me. I even offered to help, and they said no!” It may be that the other person is trying to be polite, and not to burden you down with this extra work.

This is illicit judgment of another person’s heart, based on these outward actions.

Now, the cunning person may use Scripture in an attempt to justify what he does. After all, doesn’t Jesus himself tell us that you can judge a person’s heart, just by looking at their actions? Doesn’t Jesus say, “By their fruits you shall know them?”

Fruit Inspection

As we read in the Gospel of Matthew,

"Beware of false prophets which come to you in sheep’s clothing but inwardly they are ravening wolves. Ye shall know them by their fruits. Do men gather grapes of thorns or figs of thistles? Even so every good tree bringeth forth good fruit, but a corrupt tree bringeth forth evil fruit. A good tree cannot bring forth evil fruit, nether can a corrupt tree bring forth good fruit. Every tree that bringeth not forth good fruit is hewn down, and cast into the fire. Wherefore by their fruits ye shall know them."

What kind of fruit is Jesus talking about here? Is he saying that we have the ability to judge each and every word and outward action of our brother? Or, is he only referring to a certain number of specific behaviors which serve as a litmus test? St. Paul in the book of Galatians says,

"Now the works of the flesh are evident, which are adultery, fornication, uncleanness, lewdness, idolatry, sorcery, hatred, contentions, jealousies, outbursts of wrath, selfish ambitions, descensions, heresies, envy, murders, drunkenness, revelries and the like which I tell you beforehand, just as I also told you in time past that those who practice such things will not inherit the kingdom of God. But, the fruit of the spirit is love, joy, peace, long-suffering, kindness, goodness, faithfulness, gentleness, self control, against such there is no law."

The Church Fathers wrote quite a bit on this topic. St. John Chrysostom says,

It does not seem to me that false prophets here refers to the heretics, but rather to persons who live morally corrupt lives while wearing a mask of virtue. They are usually called frauds by most people. For this reason Jesus continued by saying,”By their fruits you will know them.” For it is possible to find some virtuous persons living among heretics. But among the corrupted of whom I speak it is no way possible. “So what difference does it make,” Jesus says in effect, “if even among these false prophets some do put on a hypocritical show of virtue? Certainly they will soon be detected easily.” The nature of this road upon which he has commanded us to walk is toilsome, and hard. The hypocrite would seldom chose to toil, but would prefer only to make a show. For this very reason the hypocrite is very easily detected. When Jesus notes that there are few who find it, he distinguishes those who do not find the way, yet pretend to find it. So do not look to the mask, but to the behavioral fruits of of those who pursue the narrow way.

St. Cyril of Alexandra said,

There may be some who in the beginning believed rightly, and assiduously labored at virtue. They may have even worked miracles and prophesied and cast out demons. And yet later they are found turning aside to evil, to self-asserted deception and desire. Of these, Jesus remarks that he never knew them. He ranks them as equivalent to those who were never known by him at all. Even if they at the outset had lived virtuously, they ended up condemned. God knows those whom he loves, and he loves those who single-mindedly believe in him and do the things that please him.

St. Augustine says,

But from their actions, we may conjecture whether this their outward appearance is put on for display. For when by any temptations those things are withdrawn or denied them which they had ether attained or sought to attain by this evil, then needs must that it appear whether they be the wolf in sheep’s clothing, or the sheep in his own.

Then finally St. Gregory,

Also the hypocrite is restrained by peaceful times of the holy church, and therefore appears clothed with godliness. But let any trial of the faith ensue, and straight the wolf — ravenous at heart — strips himself of his sheepskin and shows by persecuting how great his rage against the good.

We have saints of the church telling us that we can know people by their fruits. By looking at their actions we can identify the wolves in sheep’s clothing, and thus distinguish them from the true sheep. We also have saints of the church telling us to avoid the sin of cunningness. We are forbidden to judge the hearts of other people, merely based on their words and outward actions.

Are the fathers of the church sending us mixed messages? Are they contradicting one another? Let us take a look at the differences between sinful cunningness, and godly fruit-inspection of those who are wolves in sheep’s clothing.

We were given a list in Galatians 5. The works of the flesh are adultery, fornication, uncleanness, lewdness, idolatry, sorcery, hatred, contentions, jealousies, outbursts of wrath, selfish ambitions, descensions, heresies, envy, murders, drunkenness, and revelries. The fruit of the Spirit is love, joy, peace, long-suffering, kindness, goodness, faithfulness, gentleness, and self control.

The fathers were not contradicting each other. Fruit-inspection is very different from cunningness. And we can see at least four ways in which they are different.

God’s Commands vs. Personal Preferences

Fruit inspection involves cases were the wolf in sheep’s clothing has violated clear commands of God: adultery, lying, unwillingness to forgive. These are things which are not based on our own opinions, these are things which are not based on our own reasonings, these are things which are revealed in holy Scripture as being works of the flesh. God himself tells us that those who practice such things will not inherit the kingdom of God. If God says that adultery is a work of the flesh — then if you find out someone is practicing adultery, and yet they pretend to be a christian — you know, there’s a wolf in sheep’s clothing.

Cunningness is not a violation of a clear command that God has given. Cunningness is a violation of your own personal preferences. “I don’t like that look on his face.” “I really don’t like that tone of voice that she gave me.” There is nothing in Scripture, or in the teachings of the fathers, which tells us that it is direct violation of God’s commands for you to make a particular look with your face, or to use a particular tone of voice, or to buy a piece of land or to sell a piece of land, or to stand and talk for a while, or to hurry and run off because you have an appointment. In these cases, the cunning person is not getting upset because a clear law of God has been violated. The cunning person gets upset because his own preference has been violated.

Sins Against Others vs. Sins Against You

When you are inspecting the fruit of the sheep, to find out whether they are sheep or not, it’s usually a case in which that person has sinned against God and their neighbor. It’s not necessarily a case were they have sinned against you yourself.

If I find out that somebody has committed adultery, in most cases that’s not going to be a situation that I was involved in personally. They certainly didn’t commit adultery with me or my wife. Maybe it was nobody in my family. I just find out that they have done this thing which God has commanded not to do.

But when a person is cunning they get angry, because,

Ah, they have violated me, they have upset me, they have hurt me. I wanted them to talk with me longer and they didn’t talk with me longer. I wanted them to give me a different look with their face, but they didn’t. They gave me this other look with their face.

Now, there are exceptions to this point, because obviously somebody may violate God’s command, and be attacking your personally. But the distinction is still very important. The person who is looking for wolves in sheep’s clothing is going to be just as upset over somebody violating God’s command, to hurt somebody else, as they will be upset with that person for violating God’s command, to hurt them. The cunning person is self-centered. Their anger at the other person’s actions doesn’t flare up when that other person gives those actions to other people. The cunning person’s anger flares up whenever they take it as a personal affront to their personal pride.

Humility vs. Pride

When you are inspecting the fruit, you humbly see that God’s commandments reveal another person to be a wolf in sheep’s clothing. But when you are cunning, you arrogantly subject another person to your own personal judgments and preferences. Again, it’s that question of “What’s your criteria?” Is your criteria for judgement the commands of God, or is your criteria for judgement your own personal ideas and opinions and preferences?

Godly Counsel vs. Gossip

Godly fruit-inspection is done with godly counsel. You seek advice from other godly people. Even if somebody has apparently violated a clear command of God, you still check with other people you trust, other people you know to be godly, and you say, “Are you seeing the same thing that I’m seeing?” And you agree that Scripture and the Church prohibit this particular activity, that this is a sin against God. You are humble enough to seek counsel from other people, before you confront.

Cunningness can be done without counsel, for you have made your own mind up, and you need no advice from anyone. Or if you do it with counsel, it is merely gossip. Instead of intentionally seeking out godly people and looking for their advice, you seek out other people who are cunning just like you, and you seek their affirmation.


  1. Godly fruit-inspection is something you do in relation to people who have violated clear commands of God. Cunningness is where you seek out people who have violated your own personal preferences.
  2. Godly fruit-inspection involves people who usually have sinned against God and their neighbor. Cunningness usually involves people who have upset you personally.
  3. Godly fruit-inspection is a case where you are humbly seeking what God has commanded, what God has revealed. With cunningness, you arrogantly are subjecting another person to whatever your own opinions are.
  4. Godly fruit-inspection is done with godly counsel, where you seek advice from godly people. And cunningness is done without counsel, or it’s done with gossip, where you seek affirmation from other cunning people.

These are some of the ways that we can see a clear difference between cunningness, and the inspection of fruits that Jesus commands us to do. As we read in one of the readings during matins this morning, Jesus himself says to “judge with righteous judgement” (John 7:24). Righteous judgement is not something to be avoided; it’s something to be pursued. Its the cunning unrighteous judgement that we are to avoid.

An Antidote for Cunningness

In the book referenced earlier, the author discusses humility as an antidote to the sin of cunningness. He says,

Cunningness is the enemy of humility. The humble individual is ready and willing to listen to others and hear their advice. Even great saints who became witnesses to reveal truth that descended directly from God sought the advice of others because they did not rely exclusively on their own perceptions. The humble person always seeks a dialogue, and is not rigidly trapped in his own opinions and ways of thinking. He leaves space for a conversation with others; he is always ready to listen. The humble person does not believe blindly in his own thoughts. He always places a question mark at the end his thought and seeks the advice of others.

As we have learned from the saints, wolves in sheep’s clothing are revealed in the midst of labor, toils, trials, and temptations. St. John Chrysostom said that wolves in sheep’s clothing will not walk the road which is toilsome, and hard. St. Augustine said that wolves in sheep’s clothing cannot stand up under temptations. And St. Gregory tells us that when peaceful times cease, and trials of faith come upon the church, wolves in sheep’s clothing will be revealed, and they will show their true colors.

So, true sheep — those who truly are Christ’s sheep — will be the opposite of this. If you are a true sheep, then you will walk the road that is toilsome and hard. You will be able to stand up under temptations without falling. And even when peaceful times cease and the trials of faith come upon the Church, you will still demonstrate though your words and your actions that you are faithfully following Christ.

Chrysostom talks at length about true sheep. Chrysostom says,

Whereas his teaching has up to now largely focused on the future kingdom, its unspeakable rewards and its consolations, now he shifts his focus to the present life, its current fruits, and how great is the strength of virtue within it.

What then is its strength? It is living with security, not easily being overcome by any of life’s terrors, and standing above all those who treat others maliciously. What could be as good as this? For not even the one who wears the royal crown would be able to furnish this for himself, but one who pursues the way of excellence can have this stability. For that one alone is possessed of this equilibrium in full abundance.

In the crashing surf of the present circumstances, such a one experiences a calm sea. This is amazing! It is when the storm is violent, the upheaval great, and the temptations continual, that such a person is not shaken in the slightest. This is not a way of living that applies to fair weather only, for he says, “The rain came, the floods came, the winds blew and they beat against that house and it did not fall, because it was founded on the rock.”

In referring to rain, floods, and winds, Jesus is speaking about all those human circumstances and misfortunes, such as false accusations, plots, bereavements, deaths, loss of family members, insults from others, and all the horrid things in life about which one could speak. Jesus says that a soul that pursues the way of excellence does not give in to any of these potential disasters, and the cause of this is that this soul has been founded upon the rock.

Now, “rock” refers to the reliability of Jesus’s teaching, for his commands are stronger then any rock. They place one quite a bit above all the human waves of life, for the one who guards these commands with care will excel not only over human beings when treated maliciously, but even over the demons themselves in their plots.

This is from one of the commentaries of St. John Chrysostom on the book of Matthew.

We are to be true sheep, not wolves in sheep’s clothing. We know what the works of the flesh are. If we are to be true sheep, then we must avoid those works of the flesh, lest we deceive ourselves. We know what the fruits of the Spirit are. If we are to be true sheep, then we must diligently seek those fruits of the Spirit in our own hearts and minds and lives.

True sheep receive strength from God, enabling them to stand in the midst of trials, and to enjoy peace in the midst of the storm. The cold winds will howl, the storm will rage, and the waves will crash, but our house will remain steadfast and unmoved, because we have built it upon the rock of Christ.

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