The Art of Discernment

I've made decisions I was certain about that turned out to be completely wrong. And I've had gut feelings I couldn't justify that turned out to save me from disaster. Over the years, I've come to believe that discernment — the ability to see past the surface of a situation and understand what's actually happening — is one of the most important skills a leader can develop.

And it is developed. Not downloaded. Not instant. Not a gift that some people have and others don't.

Discern the Spirit, Not Just the Words

This is perhaps the hardest lesson. Words can be technically true and fundamentally misleading. Tone can be warm while intent is cold. A proposal can look perfect on paper and be designed to exploit you.

There's a fascinating moment in the book of Acts where Paul encounters a slave girl who follows him around declaring, "These men are servants of the Most High God, who proclaim to you the way of salvation." Every word she said was accurate. The content was true. But Paul discerned that the spirit behind the words was wrong, and he addressed that rather than the words themselves.

This has enormous practical implications. In business, I've received proposals that said all the right things — the language was professional, the promises were specific, the references checked out. But something felt off. When I've ignored that instinct, I've regretted it. When I've honoured it and dug deeper, I've usually found what was hidden.

In relationships, I've encountered people who say exactly what I want to hear. Flattery is easy to spot when it's clumsy. It's almost invisible when it's skilled. Discernment means listening to what's not being said as carefully as what is.

Guard Against Deception

The oldest story of deception in Scripture involves a manipulation of words. The serpent didn't lie outright to Eve — at least not at first. He reframed. He questioned. "Did God really say...?" He took something true and tilted it just enough to change its meaning.

I see this constantly. In business pitches. In organizational politics. In social media arguments. In well-intentioned advice that subtly redirects you away from what you know to be right.

Good-sounding messages can mislead. That's not cynicism — it's realism. And the defence against it isn't suspicion of everything, which makes you paranoid and impossible to work with. The defence is trained discernment, which allows you to engage openly while remaining alert.

How Discernment Develops

The writer of Hebrews puts it plainly: "Solid food belongs to those who are of full age — those who by practice have their senses trained to discern both good and evil."

By practice. By constant, repetitive, often unglamorous practice.

Discernment develops when you make a decision, observe the outcome, and honestly assess whether your read of the situation was accurate. It develops when you reflect on the times you were fooled and identify what you missed. It develops when you seek counsel from people who see differently than you do.

In my experience leading across multiple domains — technology, church life, and palliative care — I've found that discernment sharpens fastest in these conditions:

Diverse exposure. The more different types of people and situations you encounter, the better your pattern recognition becomes. Running an IT company exposes me to business deception. Pastoring a church exposes me to spiritual manipulation. Working in palliative care exposes me to emotional exploitation of vulnerable people. Each context trains a different aspect of discernment.

Honest feedback loops. I ask people I trust to evaluate my decisions — not after a crisis, but routinely. "Did I read that situation right? What did I miss? What would you have done differently?" This only works with people who will actually tell you the truth.

Reflection, not just reaction. Most bad decisions happen fast. Discernment requires enough space to think. I've learned to say, "Let me sit with this before I respond" — not because I'm indecisive, but because my first instinct isn't always my best one.

Accumulated experience. There's no shortcut for this. A twenty-five-year-old can be intelligent, talented, and capable. But discernment of the kind I'm describing usually requires years of seeing patterns play out. This is why wise leaders value age and experience on their teams, even in industries that worship youth.

The Cost of Not Developing It

Leaders without discernment get exploited. They hire the wrong people. They partner with the wrong organizations. They trust the wrong voices. And when it goes wrong, they're genuinely shocked — because the words all sounded right.

Develop your senses. Train them by practice. Learn to hear what's not being said. And when something feels off, don't dismiss that instinct. Investigate it.

Discernment isn't suspicion. It's wisdom with its eyes open.