Why Mentors Should Stay at the Table When Things Get Hard

Opening Story

Matthew looked like he wanted to disappear into the tile floor.

The smell of chlorine hit me the moment I walked into the indoor pool, thick and sharp in the air. Kids’ voices echoed off the walls, and somewhere in the background a lifeguard’s whistle cut through the noise.

Matthew was sitting on the edge of the pool with his feet in the water, fully dressed and not even pretending to swim. His hood was up, even though it was humid, and he kept dragging his heel along the tile like he was trying to erase himself.

I sat down a few feet away and did not say anything at first. After a while, I asked why he did not want to get in.

Matthew shrugged, kept his eyes on the water, and said it was stupid.

I could have left it there, but something felt off, so I stayed quiet a little longer.

Eventually, he let out a long sigh and said, almost under his breath, “I don’t know how to swim.”

It was not just a statement. It felt like a confession.

As we kept talking, it became clear that it was not really about swimming. Matthew was tired of being the kid who did not know things, the one who always felt behind, the one who expected people to laugh if he tried.

I felt the pull to jump in and fix it, to turn it into a quick lesson or a plan to get him caught up. But I could also sense that if I moved too fast, I would miss what was really happening underneath the surface.

What Matthew needed most in that moment was not a solution to his problem. He needed a safe place to admit it without feeling small.

The Core Problem

I’ve seen this play out over and over again in mentoring, especially when we’re working across differences like race, class, and culture. We tend to come in thinking the primary challenge is what we can see. We focus on behavior, habits, and outcomes. We want to help a kid read better, act better, or make better decisions. Those things matter, but they’re rarely the root issue. What we’re actually stepping into is a layered story shaped by experiences, systems, family dynamics, and often pain that we don’t fully understand.

The problem is that when we don’t recognize that complexity, we default to control or quick fixes. We create plans, strategies, and expectations that make sense to us, but don’t actually connect with what the kid is carrying. In the worst cases, we slip into a subtle savior mentality without even realizing it. We think we’re there to help, but we’re really there to lead, fix, and direct. When I approach mentoring with the assumption that I am the solution, I stop listening closely enough to understand the real need.

This becomes even more complicated when cultural or racial differences are involved. There are histories, assumptions, and internal reactions that surface whether we acknowledge them or not. If I’m not paying attention to what’s happening inside of me, I will either avoid those tensions or react to them in ways that damage trust. I’ve had to face moments where I realized my instincts were shaped more by bias or fear than by love or understanding. Those are uncomfortable moments, but they are necessary ones.

The Core Principle

Over time, I’ve come to believe something simple but demanding: the work of mentoring across difference begins with humility, grows through compassion, and is sustained by staying connected when it gets hard.

Humility is what allows me to walk into a relationship without assuming I already understand it. Compassion is what helps me care about the person in front of me beyond what they can offer or achieve. And staying connected is what keeps the relationship alive when tension inevitably shows up. Because it will show up. There will be moments when I feel misunderstood, moments when I don’t know what to say, and moments when I want to pull back because it feels easier than pressing in.

The temptation in those moments is to disengage, even if it’s subtle. I might not physically leave, but I emotionally check out. I stop asking deeper questions. I stop listening with curiosity. I start protecting myself instead of investing in the relationship. But I’ve learned that those are often the exact moments where growth is possible, if I’m willing to stay.

Expanded Insight

One of the most important shifts I’ve had to make is moving from seeing myself as the author of a kid’s story to recognizing that I am stepping into a story that is already being written. That changes everything about how I show up. When I think I’m the author, I feel pressure to get it right, to fix things quickly, and to produce results. When I see myself as a participant, I become more attentive, more patient, and more open to what God might already be doing.

I’ve had conversations with mentors who are frustrated because their mentee isn’t changing fast enough. They feel like they’re investing time and not seeing results. I understand that feeling, because I’ve been there. But I’ve also had to ask myself a harder question: am I measuring success by my timeline, or by what this kid actually needs right now? Sometimes what looks like a lack of progress is actually a lack of trust, and trust takes longer to build than most of us expect.

There have been moments where I realized that what I thought was resistance was actually fear. What I interpreted as disrespect was actually insecurity. What I labeled as disinterest was actually a lack of belief in themselves. Those realizations don’t happen when I’m rushing or assuming. They happen when I slow down enough to listen, observe, and stay present.

This becomes even more significant when I think about the realities many kids are facing. When a child is growing up in an environment shaped by instability, poverty, or systemic challenges, they are learning lessons about the world that shape how they respond to me. If I don’t take the time to understand that, I will misread their behavior. I will respond to symptoms instead of causes.

I’ve also had to confront what’s happening inside of me in these relationships. There have been times when I felt more comfortable with certain kids than others, and I had to ask why. There have been moments when I made assumptions based on appearance, tone, or background. Bringing those things into the light has been uncomfortable, but it has also been freeing. Anything I hide has power over me, but anything I bring into the light can be transformed.

Another layer to this is understanding that connection is the foundation for everything else. Skills matter. Structure matters. But without connection, none of it sticks. I can have the best plan in the world, but if a kid doesn’t feel seen, valued, and safe with me, that plan won’t go anywhere. Connection is what creates the environment where growth can happen.

And connection isn’t built in easy moments. It’s built in the moments where I choose to stay when it would be easier to step back. It’s built when I lean into awkward conversations instead of avoiding them. It’s built when I listen without rushing to respond. It’s built when I admit I don’t have all the answers.

Here are some practical ways to apply this principal:

1. Stay in moments of tension instead of retreating from them.
   One of the most important things I can do is intentionally stay in moments of tension instead of retreating from them. When a conversation becomes uncomfortable or when I feel misunderstood, my instinct is often to pull back or change the subject. Instead, I’ve learned to slow down and ask myself what is actually happening beneath the surface. I might say something as simple as, “Help me understand what you’re feeling right now,” and then commit to listening without interrupting. Those moments often open doors that would have stayed closed if I had chosen comfort over connection.

2. Check your internal posture before stepping into a mentoring moment.
   I also need to regularly check my internal posture before I step into a mentoring moment. It’s easy for me to carry in my own expectations, frustrations, or assumptions without realizing it. Before I meet with a kid, I’ve started taking a few minutes to pause and ask myself whether I’m coming in to control the moment or to understand it. When I enter with humility, I notice more. I ask better questions. I respond with more patience. That small shift in preparation changes the tone of the entire interaction.

3. Ask better questions instead of making quick statements.
   Another practical step is learning to ask better questions instead of making quick statements. When a kid does something that doesn’t make sense to me, my first instinct is often to correct or redirect. But I’ve found that asking questions like, “What was going through your mind when that happened?” or “What made that feel like the right choice in that moment?” gives me insight I would have missed otherwise. Those questions communicate that I care about their perspective, not just their behavior.

4. Expose yourself to perspectives and experiences different from your own.
   I’ve also had to become intentional about exposing myself to perspectives and experiences that are different from my own. That doesn’t happen accidentally. It requires me to seek out conversations, relationships, and resources that challenge my assumptions. Whether it’s listening to someone’s story, reading something outside my normal lens, or simply spending time with people who have lived different experiences, that intentionality expands my understanding and deepens my compassion.

5. Practice confession and accountability when you recognize bias or missteps.
   Another step is practicing confession and accountability when I recognize bias or missteps in myself. There have been moments where I’ve realized I made an unfair assumption or responded in a way that wasn’t rooted in love. Instead of ignoring those moments, I’ve learned to bring them into the light, both in my relationship with God and with trusted people in my life. That process keeps my heart soft and reminds me that growth is ongoing.

6. Anchor your role as a mentor in something bigger than yourself.
   Finally, I need to consistently anchor my role as a mentor in something bigger than myself. I am not the savior in this relationship, and that’s a good thing. When I remember that God is already at work in the life of the kid I’m mentoring, it takes the pressure off of me to produce outcomes. It shifts my focus from performance to faithfulness. My job is to show up, to love well, and to pay attention to where I am being invited to participate in what is already happening.

Conclusion (Bottom Line)

When I think back to that conversation at the table, I realize that the moment wasn’t really about reading at all. It was about a kid trying to make sense of his future and his place in the world. It was about dignity, opportunity, and the quiet awareness that he would have to fight for things that others might take for granted. And in that moment, I wasn’t there to fix everything or to provide all the answers. I was there to listen, to care, and to stay.

Mentoring across difference will always involve tension, because it requires me to step outside of what is familiar and comfortable. But I’ve come to believe that those tensions are not obstacles to avoid; they are invitations to grow. If I am willing to stay at the table, to listen with humility, and to lead with compassion, I will begin to see people not as problems to solve but as stories to honor. And in that space, real transformation becomes possible, not because I forced it, but because I was present enough to participate in it.

Discussion Questions

1. When you experience tension or discomfort in a mentoring relationship, what is your instinctive response, and what would it look like for you to stay engaged instead of pulling back?

2. In what ways might your assumptions or expectations be shaping how you see your mentee, and how can you begin to replace those assumptions with deeper understanding?