Developing Good Discernment: Navigating Between the Twin Errors of Cynicism and Naivete in Christian Leadership

Josh Benadum Substack

 The article originally appeared on Josh Benadum's Substack. Used with permission. Check out Josh's latest book, A Life That Leads, for more of his writing.

In the context of a house church or a tight-knit missional community, we don’t have the luxury of hiding behind large programs, administrative bureaucracy, or sheer numbers. We are dealing with people up close and personal. When the messy reality of human brokenness inevitably surfaces, it becomes immediately apparent that good intentions are not enough to lead a community well. Because of the risks we take on through such proximity, one of the most critical skills any spiritual leader can develop is discernment.

The New Testament concept of discernment is rooted in the Greek word diakrisis, which is a derivative of the verb diakrino, meaning “to evaluate carefully”. It refers to the ability to evaluate and judge—to possess the capacity to make judgments and decisions.

For many modern Christians, discernment is categorized purely as a mystical ability, something reserved for those gifted, like a sixth sense or special intuition. It certainly could be related to spiritual gifts. After all, the Apostle Paul writes, “For to one is given the word of wisdom through the Spirit... to another distinguishing between spirits” (1 Corinthians 12:9-10). However, while some may have a unique charismatic gifting, we miss the Biblical mark if we stop there. Discernment is an essential characteristic expected on some level of all believers.

Consider how the writer of Hebrews describes spiritual maturity:

“But solid food is for the mature, who because of practice have their senses trained to discern good and evil.” (Hebrews 5:14)

Similarly, Jesus rebuked the crowds of His day for their lack of spiritual awareness, demanding that they open their eyes to the spiritual realities playing out right in front of them:

“You hypocrites! You know how to analyze the appearance of the earth and the sky, but why do you not analyze this present time? And why do you not even on your own initiative judge what is right?” (Luke 12:56-57)

In the Old Testament, the book of Proverbs links discernment directly to our spiritual survival, guidance, and flourishing:

“My son, do not let wisdom and understanding out of your sight, preserve sound judgment and discretion; they will be life for you, an ornament to grace your neck. Then you will go on your way in safety, and your foot will not stumble.” (Proverbs 3:21-23)

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The High Stakes for Spiritual Leaders

While expected of everyone, discernment matters greatly for leaders. There can be inordinate cost in making foolish or hasty decisions, that then have a detrimental effect on the entire Christian body.

Think about the damage that occurs when we empower the wrong person too quickly, or when we fail to sense a toxic, divisive dynamic before it erupts and fractures a small church community. Conversely, think of the immense kingdom impact we forfeit when we fail to recognize a quiet but deeply faithful servant, or spot an incredible open door for new ministry.

In my years of planting and leading house churches, I have learned that good discernment is a major key to:

  • Avoiding serious danger.

  • Seizing on key opportunities.

  • Wise use of time.

  • Effective ministry initiatives.

  • Developing future leaders.

Discerning Spiritual Authenticity

One of the most frequent and complex areas for discernment involves evaluating individuals. In discipleship, counseling, and leadership development, we are constantly having to ask ourselves a blunt but necessary question: “What is really going on with this person spiritually?” This isn’t about fully judging a person’s motives or making some sort of wholesale assumption about what they will do with their life. It’s about doing the best we can to figure out where to invest our time, and who to entrust with key responsibilities, based on what can realistically know about a person.

Answering this question is incredibly difficult because of several confounding factors.

  • Everyone has sin and suffers setbacks. We cannot expect perfection from the people we serve, nor from ourselves.

  • Compliance isn’t necessarily spirituality. A person can smile, nod, agree with your theology, and show up to every gathering without ever actually surrendering their heart to Jesus.

  • People have different starting points. A massive step of faith and obedience for someone from a deeply broken background might look like baseline behavior for someone raised in the church.

  • We can’t ever see people’s hearts. We are not omniscient, and we must humbly acknowledge our limits.

So, how do we discern reality from religious performance? We must train ourselves to look for meaningful observations over time rather than superficial impressions. We need to evaluate whether someone is making a real effort versus making no effort or simply faking it. We must contrast someone who combines talk with action versus someone who does nothing more than talk.

Instead of looking at isolated incidents, consider trajectories which reveal long term patterns: are they trending up in terms of their spiritual growth, attitude, and character? Or is the picture instead one of decline over the course of time? Observe their relationship with the truth—it’s extremely difficult to trust someone who shows themselves to be a consistent liar, or comfortable with any level of deceit. Are they genuinely excited about spiritual things? Or are they only truly animated by entertainment opportunities, or other forms of personal gain?

Other powerful indicators of a person’s spiritual state could include:

  • Are they full of new insights versus remaining dutiful or dull?

  • Are they confident and secure in Christ versus fearful and insecure?

  • Do they exhibit true repentance versus mere worldly remorse?

  • Do they serve regularly (and without recognition) versus avoiding serving (or only doing so when it earns them approval)?

  • Do they agree with God (scripture) versus agreeing with Satan (lies)?

When people are genuinely walking with God, a certain open-handedness and spiritual courage begin to emerge. But Proverbs 28:1 tells us, “The wicked flee when no one is pursuing, But the righteous are bold as a lion”. People who are avoidant and defensive typically have something to hide.

Evaluating Group Dynamics

Discernment isn’t strictly an individual diagnostic tool; it is also highly applicable to groups. When assessing the health of a church or a ministry team, leaders need to be able to discern the corporate spiritual state, the group’s morale, and the level of unity.

You have to keep your finger on the pulse of the community, being on the lookout for toxic elements like unrighteous competition, while simultaneously scanning the horizon to identify emerging leaders.

Cultivating the Skill of Discernment

If discernment is both a divine gift and a spiritual muscle, how do we strengthen it? How do we transition from being easily fooled by outward appearances to possessing the robust, but still gracious discernment required for leadership?[1]

1. Know Your Bible Deeply: Having good discernment requires knowing scripture deeply. You need accurate knowledge, the ability to see how it applies to real-life situations, and the ability to spot skewed emphasis in teaching or behavior.

2. Pray With an Open Mind: We must learn to pray with an open mind. Often, our pre-conceived notions cloud our ability to hear the Holy Spirit’s guidance. We must be willing to have our assumptions challenged by God.

3. Study Past Behavior (But Leave Room for Grace): We have to accept the pragmatic reality that the best predictor of future behavior is past behavior. This doesn’t mean we stop believing in the transformative power of the Gospel. The crucial qualification is always that people do change, much like the parable of the son who initially says no to his father but later repents and obeys (Matthew 21:28-32).

4. Ask Questions and Withhold Judgment: Having good discernment requires actively considering a person’s stated motivations, asking lots of questions, and ensuring you don’t jump to conclusions prematurely. Scripture warns us about the danger of hearing only one side of a story: “In a lawsuit the first to speak seems right, until someone comes forward and cross-examines” (Proverbs 18:17).

5. Seek Good Counsel: You cannot accurately discern everything on an island. Having good discernment means getting good counsel from other mature believers. As Proverbs 11:14 states, “For lack of guidance a nation falls, but victory is won through many advisers”.

6. Become a Student of Human Nature: Finally, having good discernment involves doing the hard, deliberate work to understand people. You must be genuinely curious and study people—and crucially, not just people who are like yourself. You have to learn about human motivations, defense mechanisms, desires, and the deeply rooted insecurities that often influence people’s behavior.

If your memory is poor, try to remember to take notes and go into pastoral conversations prepared, because recognizing patterns is absolutely necessary for forming an accurate understanding. You must also be informed regarding the “psychology of sin”—how individuals trapped in unrepentant sin will instinctively run, hide, accuse, turn to legalism, or blame-shift.

Good discernment requires correlating your subjective intuition with objective factors. Intuition is a wonderful starting point, but you must withhold final judgment, pray, ask good questions, and wait patiently for the evidence to reveal itself.

In the end, cultivating discernment is a lifelong journey of aligning our hearts and minds with the Spirit of God. It is a vital threshold that all true spiritual leaders must cross if they want to build authentic, transformative community, that also takes into real account the messiness of the human condition. Let’s continually seek God so that our vision becomes sharper, our love becomes wiser, and churches continue to flourish.

When we work at this skill, we also obey Jesus who commanded his disciples as they went out to do ministry: “I am sending you out like sheep among wolves. Therefore be as shrewd as snakes and as innocent as doves” (Matthew 10:16).

[1] Check out chapter 10 on this subject from my book “A Life That Leads.”

Josh Benadum (MA, Trinity Evangelical Divinity School) is a pastor and network leader in Orlando, Florida. He and his wife, Meri, serve Acacia House Churches and collaborate with Youth for Christ, Stadia Church Planting, and Brave Future. He is also the author of A Life That Leads: Pursuing Christ and Impacting Others. (edited)

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