Leadership and Discernment: Learning to Walk With People, Not Just Lead Them

Reflections Inspired by I Once Was Lost: What Postmodern Skeptics Taught Us About Their Path to Jesus (Don Everts & Doug Schaupp)

Throughout this series, we’ve explored the journey people often take as they move toward faith—learning to trust, becoming curious, opening their lives to change, and ultimately facing the invitation to surrender to Jesus. One of the clearest lessons from these thresholds is that people rarely move in straight lines or at the same pace. Every person carries different questions, fears, experiences, and hesitations along the way. 

And that reality reveals something deeply important about leadership: effective spiritual leadership requires discernment.

Leadership is often associated with vision, strategy, influence, and direction. But one of the most overlooked qualities of spiritual leadership is discernment—the ability to recognize where people are, understand what God may be doing in their lives, and respond with wisdom, patience, and grace.

In many ways, discernment is what allows leaders not simply to move people forward, but to walk faithfully with them where they are.

Throughout I Once Was Lost, Don Everts and Doug Schaupp describe the journey people often take toward faith through a series of thresholds: moving from distrust to trust, from curiosity to openness, and ultimately toward surrender to Jesus. While the book focuses on spiritual formation and evangelism, it also offers profound insight into leadership itself.

Because good leaders do more than communicate truth. They learn to discern timing, posture, readiness, and need.

“Look carefully then how you walk, not as unwise but as wise, making the best use of the time…”
— Ephesians 5:15–16 (NLT)

Discernment begins with seeing people clearly. One of the central lessons of the series is this: not everyone is in the same place on the journey.

Some people are skeptical. Some are curious. Some are quietly wrestling with deeper questions. Others are closer to faith than anyone realizes.

Discernment allows leaders to recognize those differences instead of treating everyone the same.

Too often, leaders default to assumption:

• Assuming people are ready when they are not
• Assuming resistance means rejection
• Assuming information alone produces transformation

But discernment slows us down enough to ask a better question:

“Where are they right now?”

That question changes how we lead.

When you look at the ministry of Jesus, He rarely approached people the same way twice. He challenged some directly, invited others gently, asked questions before giving answers, listened before speaking, and discerned what was happening beneath the surface.

Jesus understood that leadership is not merely about delivering truth—it is about shepherding people wisely toward it.

That requires discernment.

One of the dangers in leadership is the temptation to push people faster than they are ready to move.

Without discernment:

• Vision becomes pressure
• Passion becomes force
• Urgency becomes frustration

But discernment helps leaders recognize that transformation is often slower and more mysterious than we would prefer.People rarely change because they were cornered into it. More often, change happens through trust, patience,  honest conversations, prayer, and the quiet work of God over time.

• Discernment reminds us that leadership is not control. It is stewardship.
• Leaders who discern well are usually leaders who listen well—not just to words, but to fears, hesitations, questions, motivations, and timing.
• Discernment grows when leaders resist the urge to immediately fix, answer, or direct every situation.

Sometimes the most discerning thing a leader can do is pause long enough to understand what is really happening.

“Live wisely among those who are not believers, and make the most of every opportunity. Let your conversation be gracious and attractive so that you will have the right response for everyone.”
— Colossians 4:5–6 (NLT)

Notice the language: wisely, graciously, the right response. Discernment is not just knowing truth—it is knowing how to respond lovingly and wisely in the moment.

The threshold framework reminds us that people move at different speeds.

Some take quick steps. Others linger in questions for years. Some resist before surrendering. Others appear close but are still hesitant.

Discernment allows leaders to walk patiently without becoming cynical or controlling.

It shifts leadership from:

• Managing outcomes → to cultivating presence
• Forcing movement → to recognizing readiness
• Demanding responses → to faithfully walking alongside others

This is especially important in spiritual leadership, where only God can ultimately change a heart.

Discernment also humbles leaders because it reminds us:

• We cannot force transformation
• We cannot predict timing
• We cannot manufacture surrender

We can teach. We can guide. We can pray. We can love faithfully. But God is the one who works within people. That realization frees leaders from carrying burdens they were never meant to carry.

At its best, discernment transforms leadership from performance into shepherding. A discerning leader pays attention, walks patiently, speaks truth wisely, loves consistently, and trusts God with the deeper work.

This kind of leadership reflects the heart of Jesus—present, wise, and faithful.

Leadership is not just about helping people get somewhere. It is about recognizing where they are, discerning what they need, and walking with them wisely toward what God may be doing in their lives.

And perhaps that is one of the deepest callings of leadership:

Not simply to lead people forward, but to walk beside them with grace, wisdom, and discernment along the way.

---