Five Lessons on Reading for Leading
Because leadership is more easily detected than defined, I have transitioned much of my reading from neatly-packed modern ‘leadership’ books towards biographies, histories, and intellectual genealogies (e.g. Carl Trueman, David Wells, John Frame). Because the people of greatest historical importance have the most biographies, there is no shortage of good content for leaders to study no matter their industry. Although a great deal of ‘leadership’ content is a scam, there are some predictable places to extract lessons for leadership. I chose these lessons, leaders, and texts first because they embody virtue, but also because they show that there is no simple recipe for success. A headmaster recently told me, “I cannot find teachers to fill vacancies. I cannot find donors to meet the budget. I cannot find students to fill seats.” This essay is my answer on how to prepare to lead well when there are no clear answers. The best preparation for an unknown future is to become resilient; these five resilience-building and virtue forming lessons on reading came about in my preparation for a summer course that I am doing with Classical U. Because they are historical and across industries, they likely will have import in more contexts than academic leadership.
1. King Solomon teaches justice without harshness with the two prostitutes in 1 Kings 3.
It has long been a practice of mine to read the ‘Proverb of the day’ since there are usually 31 days in a month, and there are 31 proverbs. Due to a recent course I took on Leaders and Leadership from Dr. Albert Mohler, I spent some more time reflecting on the author of those proverbs, King Solomon. After Solomon prayed for wisdom in 1 Kings 3, God answered his prayer by providing him a situation requiring the exercise of his newly-acquired wisdom. He was faced with two prostitutes in a conflict about the death of a child. We all face ‘he said, she said’ situations where it is hard to know what actually happened and how to respond. The only data King Solomon had was provided by the prostitutes in 1 Kings 3:22 which says, “But the other woman said, “No, the living child is mine, and the dead child is yours.” The first said, “No, the dead child is yours, and the living child is mine.” Thus they spoke before the king.” Every leader has been drawn into mediating a conflict where it is unrealistic and unreasonable that they would be able to find out all of the facts of a case. Therefore, this story is an ideal reflection for leading when there is no clear way forward and for those who commit the idolatry of certainty. The best soldiers know how to fight in low-light conditions, and the best athletes can be successful in both sunshine and in inclement weather.
With King Solomon, he devised a brilliant way to find out the truth of the matter in 1 Kings 3:24-25, “And the king said, “Bring me a sword.” So a sword was brought before the king. And the king said, “Divide the living child in two, and give half to the one and half to the other.” King Solomon had the wisdom of God to do justice, to give each woman her due reward. There is no chapter and verse in the Bible that will give leaders formulaic wisdom to know how to respond to every case that comes our way. God was pleased to answer King Solomon’s prayer in 1 Kings 3:9, “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?”
In your reading diet, are you drawing upon the wisdom of Proverbs? They are one of God’s ordained means to find the sweet spot of justice in between harsh legalism (Pr. 21:13), favoritism (Pr. 28:21), and flattery (Pr. 28:23). While books like Crucial Conversations and Radical Candor do serve a purpose in mediating conflicts, I find the wisdom of Solomon to be more effective if I spend the time contemplating his teaching. A book I have benefited from, The Peacemaker, is ultimately just a book from man, and I find myself coming back over and over to the Word of God in the Proverbs. Typically, I extract one verse from a proverb and put it in my mouth like a lozenge for the day. In our zeal to read the Great Books, we must not neglect the Greatest Book. Charles Spurgeon advised his congregants to visit many good books but live in the Bible. In order to become wise, we must walk with those wise people who have gone before us (Proverbs 13:20). By hearing from David and Moses and Solomon and Paul and Jesus and James, we will find safety as a leader in an abundance of counselors (Proverbs 11:14).
2. George Washington teaches temperance without deprivation.
You may have heard the quote, “Thomas Jefferson studied at William and Mary, John Adams studied at Harvard, James Madison studied at Princeton — and George Washington went to war.” Washington is always a reminder to me that that education can only take you so far until real-world experience needs to kick in; I view the relationship between experience and education as complementary. Washington may not have known Latin and Greek but he, like Lincoln, was an avid learner, master orator, and fancied himself a modern Cincinnatus so he was not foreign to the Classical world. Charles Spurgeon, who deliberately avoided formal theological education, and George Washington are both reminders that school is not the only location where learning takes place.
As far as his virtue, George Washington showed temperance most vividly during his public farewell in 1797. At the end of his second term as President, George Washington voluntarily gave up power, something virtually unprecedented at the time. During John Adams's inauguration, Washington attended the ceremony—not as a presiding figure, but as a citizen turning over power. After Adams was sworn in, the ceremony concluded. Washington, Adams, and Jefferson were to exit the stage. As custom would suggest, Washington was still the most revered figure in the room. The others would typically defer to him. But Washington insisted that Adams and Jefferson leave before him. He had no interest in becoming a dictator which is also evident in his Farewell Address.
Temperance is the virtue of balance that keeps the other virtues in harmony, and is what Paul describes in 1 Corinthians 9:25, “Everyone who competes in the games goes into strict training. They do it to get a crown that will not last, but we do it to get a crown that will last forever.” To achieve greatness, you must develop not just physical restraint but moral restraint, or self-control. Proverbs 25:28 says, “A man without self-control is like a city broken into and left without walls." When Jocko Willink says that, “Discipline equals freedom,” it seems to be very similar to the virtue of temperance or the biblical virtue of self-control. I was introduced more fully to George Washington in 2024 when I read 1776 and was stirred to lead better. Brookhiser has a good biography on Washington and even wrote a book entitled Washington On Leadership to translate his leadership into life lessons. Washington led in impossible circumstances with both courage and restraint, or temperance. Obviously, the fullest expression of these virtues is found in Christ, and we cannot achieve them without remaining connecting to the true vine (John 15:5).
Washington was born into a slaveholding society and he himself did participate in this evil institution. In the recent past, this has caused students in schools bearing his name (George Washington High School in CA and George Washington University in Washington DC) to become scandalized and traumatized by the slaveholding legacy of our founding father. This revolutionary statue-toppling posture is a dangerous instinct, because it almost always leads to forsaking our civilizational inheritance and rejecting that which we should conserve and preserve. We can be clear-eyed morally, appreciate Washington, and condemn his slaveholding if we value the virtue of temperance. If we only named schools after perfect people, every school would be named after Jesus Christ. The very people that spit at Washington lack the virtue of temperance that he consistently yet imperfectly embodied.
3. Cicero teaches prudence without hesitation in his First Oration Against Catiline.
The first line in Cicero’s speech against Catiline to the Roman Senate in 63 BC states, “How long, O Catiline, will you abuse our patience?” Because Churchill, Jefferson, Adams, Calvin, and Augustine all examined this most famous speech from Cicero, it merits our attention even if it is not written in business prose. Catiline was a Roman senator that had conspired to murder other senators and burn parts of Rome, and Cicero exposed his plot to the Roman Senate while Catiline was present among them. Catiline was not using the political process to introduce reforms but was seeking to ignite a revolution in Rome for the advance of his own power. The speech is Cicero’s defense of the Roman republic done with both moral virtue and rhetorical brilliance. It teaches leaders how they should prudently respond to people within their school communities behaving badly.
I first heard of this speech from Cicero when reading The Statesman as Thinker: Portraits of Greatness, Courage, and Moderation by Daniel Mahoney. Mahoney paints Cicero as the picture of magnanimity and prudence so I was first confused when I first met him through a speech on how to decisively deal with a conspiring criminal in a position of power! Cicero writes, “Prudence is the knowledge of things that are good, bad, and neither.” While not everyone agreed with Cicero’s response to the planned crimes of Catiline and his followers, Cicero shows prudence in clearly spotting the evil in their midst, and dealing with it from a moral basis. Leaders will be judged by their reactions more than their actions so it is wise to study Cicero’s past reaction to a criminal so you can train your own reactions to the situations where you’ll have to make a ruling.
Cicero preferred peace to war, but he was willing to prudently go to war and exile Catiline to safeguard Rome. Cicero’s prudence teaches leaders that whatever they permit, they promote. Prudence is neither moral relativism nor is it unprincipled pragmatism. I have watched some leaders, in the name of prudence, appease agitators rather than confront them like Cicero did with Catiline in front of the Roman Senate. Churchill had a similar response to Hitler that Cicero had to Catiline; Churchill stood alone in his view while others were pursuing a strategy of appeasement. Within a school community, certain situations call for decisive action and Scripture provides guidance for these moments:
Proverbs 22:10 — “Drive out a scoffer, and strife will go out, and quarreling and abuse will cease.”
Titus 3:10 — “As for a person who stirs up division, after warning him once and then twice, have nothing more to do with him.”
Romans 16:17 — “I appeal to you, brothers, to watch out for those who cause divisions and create obstacles contrary to the doctrine that you have been taught; avoid them.”
The general principle within these verses is important for school leadership. If we are to be judged by our reactions, it is best to prepare ourselves for the most complicated situations and hope that they never happen. Cicero’s speech against Catiline has served leaders in past ages and may be useful for today’s classical school leaders as well. Studying speeches of extreme situations helps leaders differentiate between what is normal, abnormal, and pathological. 99% of situations will be far more placid than the situation with Cataline and will simply require forbearance, forgiveness, and patient counsel.
4. Winston Churchill teaches courage without rashness.
The day before Hitler initiated Operation Barbarossa to invade Stalin’s Russia in May 1940, God raised up a lion to rouse the British people, the 65 year-old Winston Churchill. Churchill had a vision which is to say that he had a message for the British people, and WWII simply revealed it. Interestingly, his anti-Nazi message was the same as his anti-Bolshevic message in WWI. He had been preparing long before he ever assumed the position. Before becoming Prime Minister at 65, Churchill had already fought in four wars, published five books, written 215 newspaper articles, was involved in three car crashes, survived two plane crashes, endured pneumonia four times, and suffered a series of heart attacks. This is similar to David who first handled sheep, the lion, and then the bear before handling Goliath and leading Israel (1 Samuel 17:37). Paul also had an impressive catalog of physical hardships (2 Cor. 11:24-31).
Daniel Mahoney captures in his excellent book The Statesman as Thinker that if there was no Hitler, there would be no Holocaust. And if there was no Churchill, there would have been no survival of Western Civilization (146). Churchill cried publicly more than 50 times during World War II and shared that he had long thought it to be his destiny to save the British empire. Churchill was not classically educated in that he had no sustained Latin or Greek (similar to Washington and Lincoln), but he did value classical rhetoric and military history based upon his time at the Royal Military Academy at Sandhurst. He was not an Evangelical and said that his religion was like the flying buttresses of the Church of England; he supported it from the outside. Nevertheless, he had the right perspective in viewing the Nazi’s as ideological barbarians who were a threat not just to Europe but to all of Western Civilization. His judgement was not infallible but he had the courage to see the Hitler-situation rightly long before the majority, and history has vindicated his hope.
Churchill’s life and leadership incarnate a quote from St. Augustine who wrote, “Hope has two beautiful daughters: their names are Anger and Courage; anger at the way things are, and courage to see that they do not remain as they are.” For a hopeful ‘vision’ to be shared by all within an academy, it must be worth crying about. If it’s not felt, it will not be fought for by the faculty and families. When nobody else would stand up and be clearly against Hitler, Churchill showed his courageous hope to the House of Commons in 1940 when he said,
We shall go on to the end, we shall fight in France, we shall fight on the seas and oceans, we shall fight with growing confidence and growing strength in the air, we shall defend our Island, whatever the cost may be, we shall fight on the beaches, we shall fight on the landing grounds, we shall fight in the fields and in the streets, we shall fight in the hills; we shall never surrender.
Churchill was not looking to the masses for morality but looking to the generations of children yet unborn.
5. The Apostle Paul teaches love without lawlessness.
John Piper writes in Why I Love the Apostle Paul, “I love the Apostle Paul because he is radically God-centered, passionate about the supremacy of Christ, and unshakably rooted in the cross.” When I first saw this free E-book a few years ago, I thought it odd to speak a love for an apostle instead of love for Christ. However, I share Piper’s love for Paul because Paul helps us look to Christ. After going through the Acts of the Apostles this year in Chapel, I have grown in my love for the Apostle. I have been particularly edified by Paul in Acts 20 where he is speaking with the Ephesian elders. I have also found encouragement in seeing in Acts how Paul takes advantage of his classical training under Gamaliel. You see Paul speaking in both Greek and Hebrew depending on his audience. Additionally, he takes advantage of his Roman citizenship and his rhetorical training at the end of Acts in his five defenses before Felix, Festus, Agrippa, the Council, and the Jews in Rome.
If we want to understand the ordo amoris (ordered loves), we should go first to Paul before looking at Augustine, Aquinas, Milton, and others. Love is the highest of the theological and virtues and the chief virtue when it comes to being misdefined and misunderstood. Paul’s farewell address to the elders in Ephesus in Acts 20 is what love from a leader should look like. It is not sentimental or indulgent as evidenced by calling out both the internal and external threats facing the church. He writes in Acts 20:28-31, “Pay careful attention to yourselves and to all the flock, in which the Holy Spirit has made you overseers, to care for the church of God, which he obtained with his own blood. I know that after my departure fierce wolves will come in among you, not sparing the flock;and from among your own selves will arise men speaking twisted things, to draw away the disciples after them. Therefore be alert…” Today, some may label this sort of warning as fearmongering, alarmist, or divisive, but the reality is that he’s a discerning watchman on the wall.
As evidenced by Acts 20:24, the source of his warning is not pride or arrogance but humility. He writes in 20:24, “But I do not account my life of any value nor as precious to myself, if only I may finish my course and the ministry that I received from the Lord Jesus, to testify to the gospel of the grace of God." Paul was humble and had plenty of reasons to not be humble; that is perhaps the hardest part of leading others. You achieve certain things in order to rise to a position of leadership yet you cannot let it go to your head. God constantly uses Paul to help me in this area. This is also why Acts 20 is a needed section for all leaders but also Paul in 1 Corinthians 15:10 when he writes, “But by the grace of God I am what I am, and his grace toward me was not in vain. On the contrary, I worked harder than any of them, though it was not I, but the grace of God that is with me.”
The most impactful leaders that I’ve observed hold on loosely to the organizations that they lead, because they love the mission and the people. I recently had dinner with a couple that founded a now-flourishing school over a decade ago. The wife said to me, “This is not our school. It is the Lord’s school. The administration needs to be strong and courageous, because the Lord goes before them.” This faith that the Lord goes before us is essential to leading with open hands yet with bold assurance.
Unlike Paul, we are not Apostles who had a face to face encounter with the resurrected Christ and were inspired by the Spirit to write Scripture. That was an office with a temporary timeline and the foundation of the church has already been laid down (Eph. 2:20). Nevertheless, I think we can follow him as he follows Christ (1 Cor. 11:1) and lay upon that foundation like a master worker (1 Cor 3).
This ‘reading for leading’ is more of a first-aid kit than a comprehensive syllabus. Tolle legge.
