How to Build Strong Communities One Mentoring Relationship at a Time

Opening Story

He stood just inside the doorway, not fully in the room, not fully out of it either. His backpack hung off one shoulder, unzipped, papers sticking out like he had given up halfway through organizing it. I noticed him before he said anything because he kept shifting his weight from one foot to the other, like he wasn’t sure if he was allowed to stay. I asked him a simple question, something like, “You heading somewhere or just passing through?” and he shrugged without making eye contact. When he finally spoke, it came out flat: “I got in trouble again.” There was no frustration in his voice, no defensiveness, just a kind of resignation that made it clear this wasn’t new. I could feel the moment trying to rush me into a response—advice, correction, something to fix it—but I held back. Instead, I pulled up a chair and said, “Tell me what happened.” He hesitated, then sat down, and for the next twenty minutes, he talked more than I had ever heard him talk before.

The Core Problem

I have learned that one of the most common mistakes I make as a mentor is assuming I understand what is happening before I actually do. When a kid says, “I got in trouble again,” my instinct is to interpret it through patterns I’ve seen before. I start categorizing. I start diagnosing. I start thinking about solutions before I have even taken the time to understand the story behind the behavior. The problem is not that I lack care; it is that I move too quickly from observation to conclusion.

This tendency shows up in subtle ways. I ask leading questions instead of open ones. I interrupt with advice disguised as curiosity. I mentally prepare my response while they are still talking. Even when I am physically present, I can be relationally distant because I am more focused on fixing the situation than understanding the person. Over time, kids pick up on this. They may still talk, but they don’t go as deep. They share enough to satisfy the moment, but not enough to reveal what is actually going on.

When I operate this way, I am not really mentoring. I am managing behavior. And while behavior might shift temporarily, nothing foundational changes because I never took the time to understand what was underneath it.

The Core Principle

The longer I mentor, the more convinced I become of a simple truth: I cannot help a young person in a meaningful way until I understand the story they are living inside of. Behavior is always connected to something deeper—beliefs, experiences, wounds, expectations—and if I skip that layer, I am building on unstable ground.

Understanding does not mean agreement, and it does not remove the need for accountability. What it does is create a foundation where accountability can actually be received. When a young person feels seen and heard, correction lands differently. It no longer feels like rejection or control; it begins to feel like care.

This principle forces me to slow down. It challenges my need to be efficient and instead invites me into something relational and patient. It reminds me that my role is not to arrive quickly at the right answer but to walk with someone long enough that the right questions begin to surface.

Expanded Insight

As he sat across from me that day, the story that unfolded was not what I expected. What started as “I got in trouble again” turned into a series of small moments that had been building for weeks. A teacher who had embarrassed him in front of his peers. A group of friends who had started excluding him. A situation at home that had left him sleeping on a couch and showing up to school exhausted. None of it excused what had happened, but all of it explained why he was on edge.

I realized that if I had responded in the first thirty seconds with correction, I would have completely missed what was actually driving his behavior. I would have addressed the symptom and ignored the source. Instead, because I waited, I was able to see the fuller picture.

There was a moment in that conversation where he looked up and said, “Nobody ever asks me all that.” It was not a dramatic statement, but it carried weight. It revealed something deeper than the situation we were discussing. It told me that most of his interactions with adults were transactional. Questions were asked to gather information, not to understand him. In that moment, I was reminded that listening is not just a skill; it is a form of dignity.

I have seen this pattern repeat itself over and over again. Kids who are labeled as difficult, disengaged, or disrespectful often carry stories that have never been fully heard. When those stories remain hidden, behavior becomes the only visible expression of what is going on inside. If I only respond to what is visible, I will always be one step behind.

This has also reshaped the way I think about accountability. Early on, I thought accountability was about clarity and consistency, and it is. But I have come to see that accountability without understanding often feels like control. It may produce compliance for a moment, but it rarely produces growth. When I take the time to understand first, accountability becomes something we move toward together rather than something I impose.

There was another mentoring relationship where this became clear in a different way. A young man I was working with kept missing our scheduled times. Each time, he had a reason, and each time, I felt my frustration building. I was tempted to confront him directly about his lack of commitment. But instead, I decided to step back and ask a different set of questions. When I did, I learned that he was working late shifts to help support his family and was often choosing between sleep and showing up. What I had interpreted as apathy was actually sacrifice.

That did not mean we ignored the inconsistency. We still addressed it. But the tone of the conversation shifted completely. Instead of calling him out, I was able to come alongside him and say, “Let’s figure out how to make this work given everything you are carrying.” Understanding transformed the conversation from confrontation to collaboration.

This is the kind of shift that changes mentoring relationships over time. It moves me from being someone who reacts to behavior to someone who interprets it. It slows me down enough to see patterns, not just moments. And it reminds me that the goal is not simply to change what a young person does, but to help shape how they see themselves and their world.

Here are some practical ways to apply this principal:

1. Ask better first questions.
   One of the first changes I have had to make is learning to ask better first questions. When a situation arises, my instinct is often to ask something that gets me quickly to the issue, like “Why did you do that?” I have found that this question can feel accusatory and shut down conversation before it begins. Instead, I try to start with something like, “Walk me through what happened.” This gives them space to tell the story in their own words and often reveals details I would not have thought to ask about. Over time, I have seen that the quality of my first question often determines the depth of the entire conversation.

2. Allow silence to exist in conversations.
   Another practice that has shaped me is intentionally allowing silence to exist in conversations. There are moments when a young person finishes speaking and everything in me wants to jump in quickly so the conversation does not feel awkward. But I have learned that those small pockets of silence often create space for deeper honesty. When I resist the urge to fill the gap, they will often continue talking and share something more vulnerable. This requires patience, but it has consistently led to more meaningful conversations.

3. Pay attention to patterns rather than isolated incidents.
   I have also started paying closer attention to patterns rather than isolated incidents. When a behavior shows up repeatedly, I try to step back and ask myself what might be underneath it. Instead of addressing each moment as a separate issue, I look for the thread that connects them. This has helped me move from reactive mentoring to more thoughtful and proactive engagement. It also allows me to address root causes rather than surface-level symptoms.

4. Reflect back what you understand before offering accountability.
   Another practical shift has been how I approach accountability conversations. Before addressing the behavior, I make it a priority to reflect back what I have heard and understood. I might say something like, “It sounds like this week has been overwhelming, and you felt like you had no control in that moment.” This does not excuse the behavior, but it communicates that I see them. From there, I can move into accountability in a way that feels grounded and relational rather than abrupt and corrective.

5. Follow up on what you hear.
   I have also learned to follow up on what I hear, not just respond in the moment. When a young person shares something significant, I try to bring it up again in a later conversation. This shows that I was not just listening to get through the moment, but that I actually value what they shared. It builds trust over time and reinforces that our relationship is not transactional. These follow-up moments often open the door to deeper conversations because they communicate consistency and care.

6. Examine your own internal pace.
   Finally, I have had to examine my own internal pace. I tend to move quickly in most areas of my life, and that can carry over into mentoring if I am not careful. Slowing down is not just about what I do externally; it is about what is happening internally. I have had to learn to notice when I am rushing toward a conclusion and intentionally pull back. This has been one of the more challenging adjustments, but it has also been one of the most impactful.

Conclusion

At the end of that first conversation, we still talked about what had happened and what needed to change. Accountability was part of it. But what stayed with me was not the resolution of the situation; it was the realization that everything meaningful in that moment came from slowing down long enough to understand. Mentoring is not about having the right response ready at the right time. It is about creating space where a young person feels seen, heard, and understood, and then walking with them from that place. When I choose understanding first, everything else—trust, accountability, growth—has a place to stand.

Discussion Questions

1. When a young person shares something difficult or frustrating, what is your natural first response, and how might it be shaping the depth of your conversations?

2. Where in your current mentoring relationships might slowing down and asking better questions lead to deeper understanding?