Bonding with Children through Challenging Conversations

By DEIB Director Leslie Sinsay

A large part of our mission as a school is to purposely create a community of students from varying backgrounds in which individual differences are respected and valued. To accomplish our mission children are exposed to topics about identity, justice, societal group dynamics, unfairness, and other aspects of the human journey of coexistence. Naturally, with their curiosity and inquisitiveness, children abound with questions.

When a child exists in a space where they feel safe and where they know patience and understanding are embedded, they start to ask questions about what most intrigues them. In a space such as Capitol Hill Day School, our children in Early Children and Elementary Grades ask questions like: 

• “Why do we call Black people Black?”
• “Why do we talk about identity?”
• “Why do we have different pronouns?” 
• “Why isn’t everyone treated the same?” 

In the Upper Grades, wonderings evolve into questions such as: 

• “How do I respond to microaggressions?”
• “How do I support my friends of color if they need it?”
• “Do I continue to be kind to someone who treats me unfairly?”  

The questions that intrigue them the most can often cause worries or nervousness for any parent or educator. As adults, how do we take notice of these feelings and still be able to answer their questions? How can we answer challenging questions and yet continue to develop and strengthen relationships with our children? There are more structured moments of questions and answers and also times when questions will arise seemingly out of the blue. Preparing as best you can for certain moments will help both you and your child. 

The first approach involves intentionally setting a time and place to have a meaningful conversation—what I call the "hot chocolate, lemonade, or Starbucks moment." Before the discussion, you can prepare by anticipating potential questions, gathering relevant context, and practicing the language you’ll use to ensure clarity and sensitivity.

The second type of conversation happens more spontaneously, with what’s called a "pop-up" question. These are unexpected questions that arise while riding in the car, walking down the street, or simply relaxing at home. These moments can be unsettling, no matter your child’s age, because they catch you off guard and may involve topics that feel too complex for them to fully grasp. Responding in these moments can make you feel vulnerable, but that vulnerability is also an opportunity. Your child will sense your honesty and openness, which can strengthen your relationship. In these moments, they may begin to see you not just as a source of knowledge, but as a trusted partner—someone they can explore and unpack difficult topics with, together.

Here are some strategies to keep in mind when having these types of conversations:

• Only answer the question that is being asked and keep it simple. This allows reflection and an opportunity for the child to make connections with prior experiences and learning in school. As adults, we tend to over-explain which can lead to confusion and misunderstandings.
• Ask clarifying questions such as: “Tell me more about what you are wondering?” and “What do you mean?” These exploratory questions can help you to be sure to form an appropriate answer to the question that the child is asking.
• Be honest in your answers.
• When you are unsure of an answer, it’s okay to tell the child and let them know you will find out an answer or that the both of you can work on finding out and learning the answer together.

For parents and educators alike, having a challenging conversation with a child is an integral part of supporting their growth and development. In conversations where the topic is an emotional one, a guiding behavior, or something more sensitive, these conversations are the bones of building trust, a resilient relationship, and a stronger bond in a parent-child or teacher-child connection.