Building a Relationship with Your Most Difficult and Challenging Student

Building a Relationship with Your Most Difficult and Challenging Students

Every teacher faces students who test boundaries, resist connection, or challenge authority. These are often the students who need us the most—those whose behaviors reflect deeper struggles, and who might be crying out for someone to see beyond their actions. Developing a meaningful relationship with these students takes time, patience, and intentionality, but the results can be truly transformative.

1. Shift Your Mindset: See Behavior as Communication

Challenging behaviors often serve as a form of communication. Students who are disruptive, defiant, or disengaged may be expressing underlying emotions such as frustration, fear, or a lack of trust. Instead of reacting to the behavior, ask yourself what the student is trying to tell you.

Example: If a student refuses to complete their work, it may not be about defiance but rather fear of failure. Instead of labeling the behavior as laziness, ask them, “What’s going on? Is there something about this assignment that’s hard for you?”

2. Meet One-on-One: The Power of Individual Connection

One of the most impactful ways to build a relationship with a challenging student is through one-on-one meetings. Taking time to meet with a student individually sends a strong message: "I care about you as a person." It allows for deeper conversations, builds trust, and helps you understand the student beyond their behavior.

A powerful story comes from a rabbi who once said, "You cannot expel a student if you have not prayed for them." This teaches us a critical lesson: we must invest personally in our students, caring for them on a deeper level before we give up on them. Meeting with students one-on-one is our way of "praying" for them—it’s taking the time to truly listen, understand, and advocate for them.

Example: Schedule time for a private conversation with your most challenging students. Ask them about their interests, strengths, and struggles. Find out what motivates them and what makes school difficult. These moments of personal connection can be the turning point in your relationship.

Tip: Use a relationship-building plan. Our Student Strengths, Challenges, and Interests Tracker helps you plan and document these meetings, ensuring that you’re taking intentional steps to connect with each student individually.

3. Offer Empathy, Structure, and Follow-Through

Students who present the greatest challenges often thrive with structure and predictability. But structure alone isn’t enough—there must be empathy behind the rules. Balancing both allows students to feel safe, while knowing that their teacher understands them and is in their corner.

Example: When a student misbehaves, rather than simply enforcing consequences, take a moment to ask how they are feeling. Address the behavior, but also offer support: “I noticed you’ve been upset lately. What’s going on?”

It’s also important to follow up on positive behavior and celebrate progress, no matter how small. A simple “I see you’re trying hard today—thank you” can have a powerful impact.

Final Thoughts: Building Relationships is an Ongoing Journey

Developing a connection with your most difficult students isn’t a quick fix. It takes time, persistence, and a genuine commitment to understanding who they are as individuals. Meeting one-on-one with them, listening to their stories, and showing empathy are crucial steps in building trust and creating a meaningful relationship.

Start today with our Relationship-Building Template to help you create meaningful connections with your students by planning individualized strategies based on their strengths, challenges, and interests. It’s a tool designed to support you in making those all-important one-on-one connections that truly make a difference.