The cultivation of character requires opportunities for knowing, enacting, and realignment of virtues in one’s life. One-on-one conversations with a mentor or even a peer can be instrumental for realignment. As we describe in Chapter 3 – How to Cultivate Virtues, “realignment involves students reflecting on where in life, specifically and concretely, they have or have not been enacting the virtues, and developing resolutions and plans for how they can better practice these virtues in the future. In Christian theological terms, realignment means evaluating the extent to which being conformed into the image of Jesus Christ.”

Step-by-Step Guide

This guide offers a step-by-step approach to facilitating a conversation with a student about their character. The conversation might occur over a cup of coffee or while washing dishes together.

Step 1. Build rapport

Before embarking on the journey of challenging students’ growth, it’s crucial to build a strong rapport with them. We recommend engaging in multiple conversations prior to a conversation about the person’s character and taking time to get to know each other. Explore first impressions and shared interests. Be an active listener. Be warm and cordial. And demonstrate your respect for the student. Building mutual trust is also a key step before engaging in an in-depth conversation about character. You can do this in several ways, like showing that you are dependable, demonstrating that you believe in the student, that you expect their best, helping them navigate sticky situations, including them in activities and special opportunities, collaborating with them as opportunities arise, and inspiring them. If this sounds like your relationship with a student, then you are ready to have deeper conversations that encourage them, help them stretch, and hold them accountable.

Step 2. Make an appointment

Next, consider the appropriate context for a one-on-one conversation with a student. By context, we mean the WHEN and WHERE. As you think about the suitable space, consider your and the student’s personalities. Some individuals are great at having personal conversations over coffee in a crowded room. Others prefer having personal conversations while walking or working together (like washing dishes). The key is to create an environment where the student feels comfortable and at ease so they can open up and engage in a meaningful conversation about virtues.

Step 3. Prepare for the conversation

Have several questions prepared for your conversation. Below, we provide a list of questions that you may consider using. After each initial question, we provided examples of follow-up questions. For more ideas, you may also want to review the questions provided in Chapter 13 – Tool: Virtue Interview for qualitative interviews. Edit these questions to better fit your particular personality, context, and student characteristics.

NOTE: Support the Community of Practice- Get creative and develop new questions for personal conversations about virtues. Share your successful ideas with others using the comment function at the bottom of this page.

Step 4. Meet with the Student 

Notice that all of the example questions start with what, how, and why – which allows students to respond openly and reflect rather than solicit simple “yes” and “no” responses. Therefore, it is important to use active listening skills when you meet with the student. Active listening is a communication skill that involves giving someone your full attention, understanding what they’re saying, and responding appropriately. It can affect both verbal and nonverbal techniques, such as:

• Pause. Pause after your questions to allow the student time to think and respond. Silence is not a bad thing!
• Paying attention. Give the speaker your undivided attention, make eye contact, nod your head, or verbally affirm students as they share without interrupting their train of thought or response. Doing so shows your interest and investment in the student. Put aside distractions and avoid mentally preparing a rebuttal.
• Acknowledging the message. Recognize that nonverbal communication can also be a form of communication. Listen to the speaker’s body language. Ask clarifying questions and follow-up questions—this can help you show interest and understanding and delve deeper into the speaker’s problem.
• Summarizing, Reflecting, or Paraphrasing. Use students’ own language in the interview. Phrases like “So what I’m hearing you share is…” reflect your careful listening and engagement. This can help you show interest and attention and clarify, confirm, and empathize with the speaker.

Step 5. Challenge Growth

As you begin to wrap up the conversation, consider how you might encourage or challenge the student in their growth. Depending on the conversation, you might consider identifying a specific virtue for them to focus on in this season of their life and recommend resources (e.g., worksheets, books, programs, etc.). You may want to ask, “I wonder if there is one thing that you can think of that I could encourage you in?” followed by, “Would it be ok if I check in with you in a week to see how that is going?”

As you challenge a student’s growth in their character, you might also allow them to use discernment to consider what the next steps in their life regarding a specific virtue might look like. The additional resources below provide a script based on Gavin Bennet’s talk,^[1] where he provides suggestions for Godly discernment on adding new spiritual practices.

 Step 6. Additional Support

Students who reflect on these questions may engage in positive and negative emotions that they would like to discuss further. Connect these students to your staff, spiritual leaders, and mental health professionals. Sometimes, we need to connect students with mental health professionals—be ready with a list of resources that you may recommend. If something comes up and you do not have a referral, ask the student if you could send some information in the next day or two.

Step 7. Follow-up

It is crucial to follow up with students after vulnerable conversations. After your discussion, students may suffer from a vulnerability hangover—i.e., a feeling of discomfort, shame, or regret that can occur after sharing personal thoughts, feelings, or experiences with others. Sending a message like “Thanks for our conversation today…” can help reduce these feelings.

additional resources