In Chapter 23 of The Prince, Machiavelli examines one of the oldest dangers of leadership: flattery. Powerful people naturally attract individuals who tell them what they want to hear. Yet a ruler who permits everyone to speak freely about everything can also lose authority and become paralyzed by competing opinions. Machiavelli therefore recommends a disciplined middle path: a wise ruler should deliberately select a small group of intelligent counselors, give them genuine freedom to tell him the truth, ask them about important matters, listen carefully, and then make the final decision himself.
Machiavelli presents Emperor Maximilian I as an example of what happens when a ruler does the opposite. Fra Luca, one of Maximilian’s officials, reportedly observed that the emperor consulted no one, yet rarely accomplished things as he intended. The problem was not that Maximilian lacked opinions or ambition. It was that he had no stable process for testing his ideas before acting.
According to Machiavelli, Maximilian was intensely secretive about his plans. He did not reveal his intentions while they were still being formed, so his advisers had no opportunity to identify weaknesses, obstacles, or unintended consequences. Only after he began implementing a plan did those around him discover what he intended.
At that point, informed objections finally emerged. Advisers would explain the practical difficulties Maximilian had failed to consider. Because he had not examined those objections during the deliberative stage, he encountered them suddenly in the middle of execution. He would then become discouraged, alter his direction, or abandon the plan altogether.
What he decided one day could be reversed the next.
His secrecy did not make him more decisive. It made his decisions less durable.
This is the irony at the heart of Machiavelli’s account. Maximilian withheld his plans because he wanted to preserve control, yet his refusal to seek counsel caused him to lose control. He appeared independent before acting, but became vulnerable to every objection afterward. Because his ideas had never been tested, they could not survive contact with informed criticism.
His advisers also could not confidently carry out his commands. They did not know whether the emperor’s current decision represented a settled judgment or merely another temporary direction. When a leader repeatedly announces plans and then reverses himself, people stop trusting the plans. They wait to see what he will change next.
Maximilian’s deepest failure was not merely insufficient information. He had created no dependable path through which truth could reach him before consequences did. He confused secrecy with wisdom and resistance to counsel with strength.
That is also the danger of the sycophant.
A sycophant protects his position by telling a powerful man what he wants to hear. He calls recklessness courage, stubbornness conviction, impulsiveness decisiveness, and pride strength. He does not always give obviously destructive advice. Often, he simply refuses to challenge the leader’s destructive tendencies.
Eventually, the powerful man stops encountering reality and begins living inside a carefully edited version of it.
This raises an important question about every center of authority, including President Trump’s circle of advisers: Are dissenting opinions genuinely welcomed, or do advisers learn that loyalty requires reinforcing what the leader already believes? This should not become merely a partisan accusation. Every president, pastor, professor, executive, investor, husband, and father should ask:
Do the people around me truly have permission to tell me I am wrong?
King David once needed exactly that kind of courageous counselor.
After Absalom, his son, was killed, David withdrew into a room and became consumed by grief. His sorrow as a father was understandable. Absalom had rebelled against him, threatened his kingdom, and sought his life, but he was still David’s son.
The problem was that David’s private grief was becoming a public failure of leadership. His soldiers had risked their lives to save him, his family, and his kingdom. Yet instead of returning to gratitude and honor, they came back quietly and shamefully, almost as though they had lost the battle. Their king appeared to mourn the enemy’s defeat more deeply than he valued the loyalty and sacrifice of his own men.
Joab entered the king’s room and confronted him:
“You have today covered with shame the faces of all your servants … because you love those who hate you and hate those who love you … Now therefore arise, go out and speak kindly to your servants.”
—2 Samuel 19:5–7, ESV
Joab reminded David that these servants had saved his life and the lives of his family. He then delivered a painful accusation: David was acting as though he would have preferred Absalom to survive even if all his loyal servants had died. Joab warned that if David did not immediately rise and speak encouragement to the people, his remaining followers would abandon him, creating a disaster worse than anything he had previously endured.
David listened.
He arose, left the room, and sat at the city gate, the public place where a king made himself available to his people. When the soldiers heard that David had appeared, they gathered before him. David’s grief remained real, but he resumed his responsibility.
A flatterer would have left David in the room.
A faithful counselor entered it.
Joab was not a flawless man, and his manner was severe. Yet in that moment he told David what no one else appeared willing to say: your pain is real, but your present conduct is injuring the people who have remained faithful to you.
Powerful men need people capable of delivering that kind of truth.
We need a small group of wise individuals who can say, “Your grief is becoming neglect. Your confidence is becoming arrogance. Your vision is becoming obsession. Your explanation does not fit the evidence. Your behavior is hurting the people who have stood beside you. You may be wrong.”
But giving people permission to criticize us is not enough. We must not punish them when they actually use it.
Many leaders claim to welcome honesty, but their anger, defensiveness, withdrawal, or retaliation teaches everyone around them to remain silent. They do not create a council of wisdom. They create a court of admirers.
Scripture tells us that faithful are the wounds of a friend. A real friend risks temporary discomfort to prevent long-term destruction. The sycophant does the opposite: he protects our feelings while abandoning our future.
I have taught philosophy, logic, faith, and critical thinking for decades, but none of that makes me immune from blindness. Intelligence can actually deepen self-deception because an intelligent man can construct sophisticated arguments for what his pride, fear, ambition, grief, or woundedness already wants.
The question is not whether people disagree with you. They probably do.
The question is whether anyone still feels safe enough to tell you.
Choose a small group of wise people. Give them permission to question your plans before they are launched, challenge your motives before they become actions, criticize your reasoning, and rebuke you when necessary. Then become the kind of man who can hear difficult truth without punishing the person who delivered it.
Maximilian concealed his plans until criticism arrived too late.
David withdrew into his grief until Joab entered the room.
Both stories reveal the same truth: power can isolate a man precisely when he most needs correction.
Powerful men do not usually fail because they lack intelligence, ambition, or ability. They often fail because isolation slowly distorts their judgment. When no one is permitted to challenge them, confidence becomes arrogance, responsibility becomes control, and private wounds begin directing public decisions.
This is one of the reasons I created Logically Faithful coaching.
I work with men carrying significant responsibilities in leadership, family, business, ministry, education, and life. Many of them do not need another admirer or another motivational speech. They need a trusted person who can help them examine their thinking, confront their blind spots, clarify difficult decisions, strengthen their faith, and move forward with greater discipline and courage.
Sometimes the strongest thing a man can do is admit that he should not navigate every battle alone.
If you are carrying responsibility but feel isolated, mentally exhausted, spiritually unfocused, or uncertain about your next step, consider whether you need someone who will encourage you without flattering you and challenge you without condemning you.
Send me a private message with the word ARISE.
We can begin with an honest conversation about where you are, what is holding you back, and what needs to change.
Do not build a court of admirers.
Build a council of wisdom.
Power without correction becomes isolation. Isolation becomes self-deception. Self-deception eventually becomes destruction.
Every powerful man needs someone courageous enough to enter the room and say:
“My brother, it is time to arise.”