Have you ever worked with someone who everyone knew wasn’t meeting expectations, but no one seemed willing to address it?
I recently attended a private school leadership conference where this very issue surfaced repeatedly. Educators shared stories of struggling employees, unhealthy behaviors, and school leaders who seemed unwilling to intervene. In many cases, it was the colleagues around these individuals who were carrying the consequences.
Of course, addressing these issues isn’t always the direct responsibility of the Head of School. Often, that falls to a principal or another supervisor. However, the Head of School plays an important role in modeling healthy accountability, equipping other leaders to have difficult conversations, and establishing a culture where problems are addressed rather than avoided.
It made me wonder how often this happens in Christian schools. We want to be gracious, patient, and understanding. But what happens when our desire to be nice prevents us from addressing what needs to be addressed?
At what point does being nice become bad leadership?
Being Nice Isn’t the Goal
Christian leaders can sometimes confuse being nice with being loving. Being nice often means keeping people comfortable and avoiding tension. Love, however, seeks what is genuinely good for another person, even when that requires an uncomfortable conversation.
Consider a teacher who consistently struggles with classroom management. Students aren’t learning as they should, parents are frustrated, and colleagues are picking up the slack. The principal recognizes the problem but hesitates to address it. Perhaps the teacher has been there for years, is going through a difficult season, or the principal simply doesn’t want to hurt anyone’s feelings.
But is avoiding the conversation really an act of love? What about the students, colleagues, and families affected? And what about the teacher being denied the honest feedback necessary to grow?
When we avoid necessary conversations, we often protect our own comfort at the expense of someone else’s growth.
Jesus Modeled a Better Way
Consider Jesus’ interaction with the rich young ruler in Mark 10:17–22. The young man approached Jesus asking what he must do to inherit eternal life. Jesus engaged him with a question and allowed him to respond. Then Mark tells us something remarkable: “Jesus looked at him and loved him” (Mark 10:21).
What followed wasn’t what the young man wanted to hear. Jesus challenged him to sell his possessions, give to the poor, and follow Him. The young man walked away disappointed because he had great wealth.
Jesus’ love didn’t prevent Him from speaking a difficult truth. He listened, asked questions, and challenged the young man to confront what was holding him back. He didn’t compromise His message to keep the young man happy.
Don’t Be Rude. Ask Questions. Listen. Then Lead.
Let’s be clear. None of this gives Christian leaders permission to be rude, dismissive, impatient, or unnecessarily harsh. Difficult conversations should be approached with humility, patience, and genuine concern for the person sitting across from us.
Dallas Willard often described love as willing the good of another. That’s particularly helpful for leaders. Our responsibility is to seek the good of the individual, but also the good of the organization and the people entrusted to our care. Sometimes those responsibilities create tension, and loving leadership requires us to navigate that tension rather than avoid it.
One mistake leaders make is entering difficult conversations with conclusions already formed. We’ve observed a problem, heard complaints, or become frustrated. By the time we meet with someone, we may be more interested in delivering our assessment than understanding the situation.
What if we started with questions instead?
How do you think things have been going?
What challenges are you experiencing?
How do you think your actions are affecting others?
What do you think needs to change?
Good questions create opportunities for honest reflection, and listening helps us understand what we may have missed. Sometimes we discover circumstances we didn’t know about. Other times, the conversation confirms that expectations aren’t being met. Either way, listening doesn’t eliminate accountability. It helps us exercise it with greater wisdom.
Of course, addressing problems doesn’t always mean immediate consequences or disciplinary action. Sometimes it requires patience, coaching, and ongoing support. But there’s a significant difference between patiently working through a problem and simply hoping it goes away.
Perhaps Christian school leadership doesn’t need fewer nice people. It needs leaders who understand that genuine love sometimes requires difficult conversations.