A man of understanding

Deuteronomy 1:13 (ESV)
Choose for your tribes wise, understanding, and experienced men, and I will appoint them as your heads.''

The second character of a leader that Moses required in the judges is a man of understanding.

The definition of this word Understanding in Hebrew is:
A primitive root; to separate mentally (or distinguish), that is, (generally) understand:--attend, consider, be cunning, diligently, direct, discern, eloquent, feel, inform, instruct, have intelligence, know, look well to, mark, perceive, be prudent, regard, (can) skill (-ful), teach, think, (cause, make to, get, give, have) understand (-ing), view, (deal) wise (-ly, man).

When Solomon asked God that He give him the ability to "discern", he was using the same word Understanding as above. He desired the ability, the understanding to separate or to distinguish between good and evil:
1 Kings 3:9 (ESV)
Give your servant therefore an understanding mind to govern your people, that I may discern between good and evil, for who is able to govern this your great people?"

Just as God in creation separated light from darkness, Heaven from Earth, leaders need the ability to discern between what is the truth and the lie, what is from God and what is from man and the devil, what is good before God's eyes and what is evil, what is beneficial and what is harmful. Without such discernment it is impossible to govern and lead a family, church or nation in a way that pleases God.

Remember when Jesus Christ said to the Church of Laodicea:
Revelation 3:15-16 (ESV)
I know your works: you are neither cold nor hot. Would that you were either cold or hot! [16] So, because you are lukewarm, and neither hot nor cold, I will spit you out of my mouth.
Christ is telling the Church of Laodicea that they have no discernment. It is all mixed, lukewarm, grey area. There was no person of understanding in the midst that could say: 'Enough is enough! This is evil before Christ's eyes. We must not do this. We must do that which is good. This is not from the Spirit of God but from the spirit of the world!' There was no clear line between things of heaven and the things of the earth, because they lacked understanding. They knew not the difference between the clean and the unclean. Therefore it was a lukewarm mix, displeasing to Christ's palate.

Understanding is not only to separate things mentally, but it is also to put things together. That is the meaning of the word "Understand" that Christ uses in this passage:
Mark 7:14-15,17-23 (ESV)
And he called the people to him again and said to them, "Hear me, all of you, and understand: [15] There is nothing outside a person that by going into him can defile him, but the things that come out of a person are what defile him." [17] And when he had entered the house and left the people, his disciples asked him about the parable. [18] And he said to them, "Then are you also without understanding? Do you not see that whatever goes into a person from outside cannot defile him, [19] since it enters not his heart but his stomach, and is expelled?" ( Thus he declared all foods clean.) [20] And he said, "What comes out of a person is what defiles him. [21] For from within, out of the heart of man, come evil thoughts, sexual immorality, theft, murder, adultery, [22] coveting, wickedness, deceit, sensuality, envy, slander, pride, foolishness. [23] All these evil things come from within, and they defile a person."
The disciples did not have understanding, that is, they could not put together mentally what Christ was saying with the occurrences of life to make sense of the parable. They could not put together that by 'things going in a person,' He meant food going in the stomach, and by 'things going out of a person', He meant the sins that proceeds from the heart that defiles the person.

It was by this kind of understanding that we believers were saved. Firstly, when we put our own wickedness together with His holiness, our actions with the Word of God, we understood how far we have fallen short of His glory. By this understanding God made us to see how we have grossly offended and violated His standards. We understood that God is angry with us, when we put together our own sins with the sins of the characters in the Bible. We saw that we deserve to die, like the characters did in the Bible. But when we were drowning in our own guilt, desiring to hide from the wrath of God, the Father revealed to us His Beloved Son, hanging on the Cross, taking the punishment for the sin of the world. God enabled us to put together in our minds that it was for OUR sins that He was crucified. Christ's death meant nothing to us previously, when we were without understanding. But when Christ by His Spirit made us to link our sins to His cross, we were united with Him by faith. His death we reckoned to be our death to sin, and His life from the dead we reckoned to be our life to God.

A man of understating is therefore a man that thinks. He is a man that considers, ponders, meditates over the things of God:
2 Timothy 2:7 (ESV)
Think over what I say, for the Lord will give you understanding in everything.
Without thinking, there can be no understanding. God will not give understanding to a man who does not think over the things of God. God has given us an amazing mind, that is able to launch deep and wide into things, and is able to process many information. He has given us logic, that can link one thing to another, cause to effect, to make sense of things. He has not given us this mind to be used on vain things, on evil things. But He gave it to be spent thinking over the things God has said, over the things He has made and has done, that we may know and understand Him.

Listen to what Christ says:
Matthew 6:26-30 (ESV)
Look at the birds of the air: they neither sow nor reap nor gather into barns, and yet your heavenly Father feeds them. Are you not of more value than they? [27] And which of you by being anxious can add a single hour to his span of life? [28] And why are you anxious about clothing? Consider the lilies of the field, how they grow: they neither toil nor spin, [29] yet I tell you, even Solomon in all his glory was not arrayed like one of these. [30] But if God so clothes the grass of the field, which today is alive and tomorrow is thrown into the oven, will he not much more clothe you, O you of little faith?
See how Christ says, 'Look at the birds of the air', and 'Consider the lilies of the field'. He is commanding us to look and think over God's creation, and understand how God provides and cares for all that He has made, especially us who are made in His image. But because we don't think over God's creation, and understand that God governs and controls all things, including us, by the power of His word, we worry and are anxious. Without thinking we are not able to receive such understanding that leads us to life and happiness.

Understanding, however, like all good things, is something that is given by God. It is surely something that we do, but the ability and the faculty is a gift that is given by God:
1 John 5:20 (ESV)
And we know that the Son of God has come and has given us understanding, so that we may know him who is true; and we are in him who is true, in his Son Jesus Christ. He is the true God and eternal life.

No man can ever understand the things of God unless God reveals them to the man. Just as no insect will ever understand a man, likewise it is infinitely more impossible that a man can understand God. But God makes it possible, by giving the man a little bit of His own mind, through His Spirit, that he may know Him:
1 Corinthians 2:11-12 (ESV)
For who knows a person's thoughts except the spirit of that person, which is in him? So also no one comprehends the thoughts of God except the Spirit of God. [12] Now we have received not the spirit of the world, but the Spirit who is from God, that we might understand the things freely given us by God.

So a man of understanding is someone who has received the Holy Spirit by God's grace. The man who understands therefore has nothing to boast of. He must be thankful that God has considered his meditations worthy, and by grace rewarded him with understanding:
Psalm 104:34 (ESV)
May my meditation be pleasing to him, for I rejoice in the LORD.
Our meditations are a way of loving God. As the greatest commandment says:
Deuteronomy 6:5 (ESV)
You shall love the LORD your God with all your heart and with all your soul and with all your might.
The meaning of the word "heart" here can also be translated as Understanding, or Mind. We are to love God will all our mind, all our understanding, with all that we are. For to not love Him is to not think about Him:
Romans 1:28-29 (ESV)
And since they did not see fit to acknowledge God, God gave them up to a debased mind to do what ought not to be done. [29] They were filled with all manner of unrighteousness, evil, covetousness, malice. They are full of envy, murder, strife, deceit, maliciousness. They are gossips,

When we don't meditate on God, God will fill our mind with trash, with evil, sin and darkness. This is because we clearly show that we don't love God when we don't think about Him. When we don't place our thoughts on God but on other things, it shows that God's word has no place in our hearts, and that we hate Him. Let us examine ourselves if God is in our minds, or if there is sin our minds:
Isaiah 55:7 (ESV)
let the wicked forsake his way, and the unrighteous man his thoughts; let him return to the LORD, that he may have compassion on him, and to our God, for he will abundantly pardon.
If God is not on our minds, Bible says we are nothing different from an animal who has no understanding:
Psalm 49:20 (ESV)
Man in his pomp yet without understanding is like the beasts that perish.

When we seek God will all our hearts/minds, then God will be found by us:
Jeremiah 29:13 (ESV)
You will seek me and find me, when you seek me with all your heart.
Psalm 27:8 (ESV)
You have said, "Seek my face."My heart says to you, "Your face, LORD, do I seek."
And God is a rewarder to them that diligently seek Him with all their heart:
Hebrews 11:6 (ESV)
And without faith it is impossible to please him, for whoever would draw near to God must believe that he exists and that he rewards those who seek him.
A man of understanding therefore is a man who diligently seeks God with his mind. The two cannot go separate. The man of understanding is not someone who is stagnant, who just sits still and expects understanding to naturally into him. But the man of understanding is someone who perpetually pursues after God with all his might, expecting the gracious fruits from God for his mental toil.

A man of understanding is therefore a man of faith. He is a man that believes that it is worthwhile to spend hours, days, months and years thinking about the things of God. He believes that God will reward him in this pursuit, not with some vain knowledge or empty wisdom, but revelation of His own Self. The man of understanding is one who loves God, and wants to know Him above all things. He has not much room in his mind for anything else, for it is filled with God. He is a man that has gladly given up knowing other things, that he may only know Jesus Christ and Him crucified:
1 Corinthians 2:2 (ESV)
For I decided to know nothing among you except Jesus Christ and him crucified.
The world may call such a man a fool, one who desires to know nothing but God, but God considers him as a wise and understanding man, for he has chosen the most important thing.

Other characteristics and fruits of the man of understanding Solomon outlines for us:
1) He is a man who does takes sin seriously and delights in the wisdom of God:
Proverbs 10:23 (ESV)
Doing wrong is like a joke to a fool, but wisdom is pleasure to a man of understanding.
2) He is a man who does not look down on his neighbors, one who considers others better than himself. Man of understanding does not speak rashly of others:
Proverbs 11:12 (ESV)
Whoever belittles his neighbor lacks sense, but a man of understanding remains silent.
3) He is a man who is able to take rebukes from others and reform himself:
Proverbs 17:10 (ESV)
A rebuke goes deeper into a man of understanding than a hundred blows into a fool.
4) He is a man that can discern what is the thoughts and the intent of another person's heart:
Proverbs 20:5 (ESV)
The purpose in a man's heart is like deep water, but a man of understanding will draw it out.
5) He is a man, as a leader, can bring prolonged peace and order, and is in favour with those he rules:
Proverbs 28:2 (ESV)
When a land transgresses, it has many rulers, but with a man of understanding and knowledge, its stability will long continue.

The man of understanding must however remember that God is the only one who understands and knows all things. He must not think that he understands all things or even 'most' things, because there are things of God that we cannot understand even with the Holy Spirit's help:
Philippians 4:7 (ESV)
And the peace of God, which surpasses all understanding, will guard your hearts and your minds in Christ Jesus.
As Paul has said:
Romans 11:33 (ESV)
Oh, the depth of the riches and wisdom and knowledge of God! How unsearchable are his judgments and how inscrutable his ways!
God infinitely larger than our tiny minds can ever find out. The best we can do is the bow down to Him and to worship Him forever. He alone is the King who reigns, He alone is the Creator who by His power simply thought and spoke the world into being. Let us humble our weak minds before the Mind that made us, and Him who thought of an unthinkable way for us to be forgiven and be reconciled back to Him. Praise be to Him:
Jeremiah 10:12 (ESV)
It is he who made the earth by his power, who established the world by his wisdom, and by his understanding stretched out the heavens.
Isaiah 40:28 (ESV)
Have you not known? Have you not heard?The LORD is the everlasting God, the Creator of the ends of the earth. He does not faint or grow weary; his understanding is unsearchable.