Leadership Discernment: Where the Wisest Man Failed

The Strategist’s Failure

I’d love to start by telling you about a recent experience with a leader named Karen. In my work as an organizational effectiveness consultant, I have the opportunity to advise and work closely with a variety of leaders. Karen is one of those leaders. In her organization, she was the definition of high-potential talent. She was savvy, system-smart, and deeply respected for her ability to navigate complex challenges. If you needed a tactical win, you called Karen.

But when she was promoted to lead a large division, those same skills stopped working for her. Almost overnight, the strategic brilliance that got her the job became the very thing that undermined her leadership.

When she received her annual 360 review feedback, she was blindsided. She expected to be praised for her leadership; instead, she received abysmal scores on trust and culture. Her team didn’t describe her as “smart” or “capable.” They described her as cold, calculating, and conniving. They felt managed, not led. They believed she was looking out for her own interests rather than the good of the organization.

Karen was shocked. She had always seen herself as well-liked and effective. As I coached her through the disorientation of this “flip,” the root cause became clear: Karen hadn’t lost her IQ; she had lost her humility. In her overconfidence, she relied entirely on her own wisdom and stopped doing the hard, humble work of discernment—listening to her people, inviting feedback, and leading with care. And as a Christian leader, waiting on the Lord to listen and trust his guidance.

In the business world, we idealize the strategic mind—the leader who is always three steps ahead, respected for their tactical prowess. We celebrate their wins and study their methods. But what happens when strategic brilliance doesn’t translate to good leadership?

But what happens when strategic brilliance doesn’t translate to good leadership?

Karen’s story is a modern parable of leadership failure, one that mirrors the arc of one of history’s wisest figures: King Solomon. The question of how someone so wise could fail so spectacularly is one that rings true in his story as well. His life serves as a timeless case study on the critical difference between strategic wisdom and true discernment—a distinction that I hope to explore. I believe that for today’s leaders, as for the kings of old, wisdom divorced from humility and obedience (and ultimately, Christ) will fail.

Solomon’s Folly

I first heard the story of Solomon when I was ten years old. In a nutshell, the story of Solomon is one of a great king raised up by the Lord to care for Israel. When the Lord offered Solomon a gift, he asked for wisdom, a choice that greatly pleased the Lord (1 Kings 3). Solomon then expanded the nation of Israel’s wealth and built the first temple. While initially seen as a great king, Solomon eventually chose to ignore God’s laws, making choices such as taking 700 wives and 300 concubines and worshipping other Gods (1 Kings 11).

Though I’m sure that whoever told me the story told it to me in its entirety, there was only one message that I walked away with: The Lord was pleased that Solomon asked for wisdom and discernment, and thus, so should I.

It has taken about 20 years for the rest of that story to catch up with me. 1 Kings 11 tells us that Solomon—the man whose prayers pleased the Lord so that in addition to a wise and discerning heart, he was also blessed with wealth and honor—ends his reign by ushering in faction and dissolution for the kingdom of Israel. His reign is the last time in the Old Testament that all of Israel’s 12 tribes are united under one king. Arguably, what started as an incredibly promising and exciting reign ended in disobedience and disappointment. Which raises the question: How did the wisest man to ever live act with such poor discernment?

His story forces us to differentiate between “wisdom”—in the business world, this is the raw, tactical intelligence we so often celebrate—and “discernment”—the harder, more humble ability to apply that wisdom with moral clarity and a deep care for people. Karen, like Solomon, had wisdom in abundance. It was discernment she lacked.

Despite being the wisest man, Solomon made gradual choices that led him away from God. In Deuteronomy 17:16-17, Moses lays down three laws for kings: they are not to accumulate vast numbers of horses, take many wives, or amass great quantities of silver and gold. Yet, throughout 1 Kings, Solomon demonstrably violates these very commands. Furthermore, he erects temples for false gods, some of whom demanded human sacrifice. The scriptures are unambiguous in stating that these decisions ultimately brought about the downfall of Israel (1 Kings 11). What could have compelled such a wise man to make such utterly foolish decisions?

One could point to many sources for his downfall: an intense love for many wives or the pride that surely came with his fame. But I’ve been reflecting on another possible reason. Perhaps the very wisdom bestowed upon Solomon, when divorced from obedience to the Lord, is what precipitated his ruin.

Perhaps the very wisdom bestowed upon Solomon, when divorced from obedience to the Lord, is what precipitated his ruin.

We must be careful not to confuse raw intelligence or even wisdom with true discernment. Wisdom in and of itself is an incredible gift from the Lord, but its application often relates to discernment. Solomon proves that it is possible to possess one without the other. Consider his downfall: from a purely political standpoint, marrying foreign wives (possibly to secure treaties) was a brilliant and wise strategy. It solidified borders, opened trade routes, and ensured peace through political alliance. Further, he built temples for his new wives to worship their foreign gods, likely a strategic part of the political maneuvering. That is wisdom in its raw, secular form.

But this strategic brilliance took place apart from obedience to and relationship with the Lord, and thus was devoid of true discernment. Solomon proves that wisdom, when divorced from obedience, doesn’t just fail—it can actively accelerate destruction. 1 Kings 11 tells us that his choices turned away his heart, which was no longer “wholly true to the Lord his God.” Solomon’s wisdom allowed him to do great things like build the temple, but his lack of discernment led him to build altars to false gods right alongside it.

Wisdom allowed him to do great things like build the temple, but his lack of discernment led him to build altars to false gods right alongside it.

Our Calling as Leaders

This lesson from Solomon’s life has profound implications for leadership today, including in the context of the business world.

In my work, I have the privilege of collaborating with incredibly brilliant and strategic leaders. While many of these leaders exhibit exceptional tactical acumen and intelligence, this savvy doesn’t always translate into effective leadership or inspire followership. In fact, it can often be perceived as cold or calculating, as we saw with Karen.

Solomon’s reign seemed to offer the promise of a golden age (1 Kings 4), but it ultimately ended in disappointment. His story teaches us that the wisest man to ever live could not succeed apart from God.

But we are not left without hope. As Jesus declared in Matthew 12, “something greater than Solomon is here.” Where Solomon’s wisdom was eventually corrupted by compromise, Christ’s wisdom was perfected by obedience.

Where Solomon’s wisdom was eventually corrupted by compromise, Christ’s wisdom was perfected by obedience.

For us as business leaders, accessing this “greater wisdom” is rarely about performative religion (as we learned so clearly through the Pharisees). It is not usually appropriate to launch into a sermon during a performance review or quote scripture in a heated negotiation. Instead, true discernment is found in the invisible rhythms of leadership. It is the quiet, daily work of asking the Lord for an obedient heart before we walk into the office. It is in how we shepherd our employees through feedback and encouragement. It is in how we bring a spirit of humility and openness to every interaction. It is found in following the admonition of St. Gregory of Nazianzus to “think of God even more often than we draw our breath.”

Some of these rhythms might include:

• Institute a Discernment Pause: Require for yourself a 24-hour mandatory “discernment moment” for significant or heated decisions. This helps you check your spirit and ensure you aren’t reacting out of fear, emotion, ego, etc., but instead a humble obedience to what the Lord is inviting you into.
• Seek Dissenting Voices: In meetings, explicitly invite dissent by establishing someone to play the role of devil’s advocate and ask the quieter voices in the room to share their thoughts and ideas as well.
• Normalize Doorframe Prayers: Have a ritual or habit that reminds you to say a small prayer before every meeting or workday. This might be a prayer reminder every time you walk through your office door, or a sticky note reminding you to pray before a Zoom meeting.
• Practice Radical Credit-Sharing: Assertively push praise downward to your team while personally taking ownership and absorbing blame whenever things go wrong. This helps leaders to regularly check their motives, examine their posture toward others, and choose humility over self-advancement.

Our call is not to reject strategy or wisdom, but to put it in its right place. We must stop asking for wisdom for its own sake and start asking for the discernment to steward that which we’ve been entrusted. When we do that, we lead with a wisdom that builds the Kingdom, rather than one that tears it apart.