Challenging Conversations: A Cheat Sheet

Challenging Conversations: A Cheat Sheet

By Elina Kats, Laura LaFave, and Elizabeth Perry

Whether your child is 5 or 15, it’s bound to happen at some point: You’ll need to initiate a challenging conversation. Has he been exhibiting a pattern of challenging behavior? Is she getting into atypical arguments with friends? Has your child been acting withdrawn, angry, sad, and you have no idea why? Has something happened within your family, community, or beyond that you want to discuss? 

Broaching these topics can feel overwhelming, and sometimes it’s hard to know how to start. University School of Milwaukee’s counselors have put together a cheat sheet for how to launch a difficult conversation, and what to say when you’re having it. 

Before You Start

Be a Model for Good Communication

Whether we realize it or not, our kids are watching how we interact with others and paying attention to how we communicate with them. The conversations we have with our family members in our home are models for how our children will connect with others outside of the home.

It’s a Moment, Not an Event

Check in with yourself. Is this topic bringing up things for you that could make this conversation bigger than it potentially needs to be? While it might feel like a big event to us because of our perspective and life experience, it might not carry the same emotional intensity for our kids. Try not to become emotionally invested in their ups and downs. Take a step back, and ask them how you could problem solve together. Do they want you to step in, or do they just need you to listen? It’s important for kids, especially as they get older, to have a sense of autonomy and agency in how they approach their friendships. It teaches them to be independent, self-reliant, and to trust themselves in their own decision making.

Find Your Spot

In taking a cue from author Sheri Glucoft Wong, make sure you align your head (logical thinking), your heart (loving consideration for your child), your gut (your instinct for what seems right), and your feet (your ability to walk the walk) before you start the conversation. That way, your messaging and conversation will carry more clarity and feel more grounded and intentional. If your child pushes back or presents a counter argument, you are aligned in your thinking from all angles. You want children to see you as a reliable source of information and boundaries. If you are wishy-washy or unclear, kids can sense you are bluffing. As much as they might disagree with you, kids deeply appreciate having boundaries, a clear sense of pattern and routine, and the knowledge they can trust their parents when they set rules.

Phrases to Begin the Conversation

“I noticed…” 

Is your child acting differently? Bring it up. Be curious. Share your thoughts on what you’ve been observing, and how you think they might be feeling as a result. Are you right? If they’d like to talk, great. Make sure you are ready to listen (see below). If not, no problem. By noticing and verbalizing your concern, you’re letting them know that you’re paying attention and are ready for a conversation when they are.

“That’s so interesting. What made you ask that?”

This is a great start when you’re not sure if you have all the information, and also when you need to catch your breath and figure out what to say next. By responding with a question,
we resist making assumptions AND we let our kids tell us what they’re interested in working through with us.

“A sad thing happened today. I’m here if you’d like to talk about it.”

We might expect that our kids know what’s going on in the world when big, catastrophic, sad, and frightening things occur, but that’s not always the case. Instead of leading with the news story or headline, start with something vague to gauge their knowledge base and interest first. You have to judge what is developmentally appropriate as well. What is the sad thing that happened? It’s ok to not share every detail, or to share information at a level you think is appropriate to your child and what they can absorb and understand. 


This one-word response can both keep the tone neutral and lead to your child elaborating on their statement. It is non-judgmental and keeps your child in charge of the direction of the conversation.

Things to Remember During the Conversation

Listen More Than You Talk

Research shows that, by simply putting feelings into words, a person experiences relief because it relieves the body’s stress response. When we listen and do NOT immediately offer solutions, we communicate that (1) what our child is saying is important enough to capture our full attention, and (2) that we - and they - can discuss big feelings and ideas without being intimidated by them. In some cases, your child might not want your solution or even for you to say anything at all, they might just want to vent. By speaking with a caring adult who is quiet and listening, they may be able to develop a solution on their own. 


Taking a deep breath buys us time to digest what we are hearing. It allows us to align our head, heart, and gut, and it protects us from responding reactively. It also ensures that silence becomes part of the conversation, which gives your child space to say more, if they need to. It can be uncomfortable to sit in silence but, if you wait, kids might fill the silence and take the conversation in an unexpected direction.

Empathize and Validate

Psychologist Lisa Damour shares that saying a simple “That stinks” can be the perfect way to let your child know that they are being heard and understood. Reflecting on their feelings delivers a needed dose of compassion to your child.

Next Steps

Never Just One

Sometimes we discuss heavy topics that we and our children need time to process. Sometimes we may not have the answers at our fingertips. Sometimes, our emotions are large enough that we are having trouble listening. Revisiting the conversation at a later time allows us to consider our child’s point of view, clarify our thoughts, and repair any mistakes we may have made. Consider revisiting the topic casually, in a way that doesn’t feel looming or overwhelming. Maybe it’s a quick check-in on your drive home, or before bed, to see how your child is feeling. Be transparent. You can say, “I don’t feel great about how our conversation ended last time, can we go back and try again?” Being vulnerable with our kids will model to them that it’s ok if we make mistakes, and not every conversation will be perfect, but we have an opportunity to go back and try again. 

Developing a Resolution 

It’s important for our children to know that we believe they are capable of solving their own problems, but that we are here to help if they need it. Ask questions to collaborate with them. “What do you think is the next step?” “What could help?” Or even, “I have some ideas. Would you like to hear them?”


Our children’s ideal conversation times may not be our ideal times. It may be easier to talk about difficult topics when we are shoulder-to-shoulder and engaged in an activity. Or, we could bring up a topic on a drive: no need for eye contact, and we can time our conversations to end when our drive is done. For parents of teens, we may need to make ourselves available late at night when their homework is done and they are eager to connect.

It’s not easy to have a difficult conversation with your child, but attempting one, even if it backfires, is better than not trying at all. It’s possible your child wants to talk to you but isn’t sure where or how to begin, or is worried they might get in trouble. Listening actively and approaching with curiosity rather than judgment can give your child the space to share with you, and to hopefully reach a resolution.  

Books for further reading:

"When the world feels like a scary place" by Abigail Gewirtz
"This is so awkward: Modern Puberty Explained" by Cara Natterson and Vanessa Kroll Bennett
"Raising Kids: Your essential guide to everyday parenting" by Sheri Glucoft Wong and Olaf Jorgenson
"The emotional lives of teenagers" by Lisa Damour

About Elina Kats

Elina Kats serves as the Middle School counselor at University School of Milwaukee. She earned a bachelor’s in anthropology and a master’s in educational psychology. She is the proud parent of a USM student, taught English in Japan, and enjoys building relationships, advocating for students, working to educate parents, and promoting mindfulness.

About Laura LaFave

Laura LaFave serves as the Preschool and Lower School counselor at University School of Milwaukee. She has a bachelor’s in math education from MSUM, where she played varsity women’s soccer, and a master’s in school counseling from the University of Dayton. Her three children attend the Preschool at USM. She enjoys empowering students to be their best selves, working with teachers and parents, as well as being active with family when not at school.

About Elizabeth Perry

Elizabeth Perry serves as the Upper School counselor at University School of Milwaukee. She has a bachelor’s in education and social policy from Northwestern University and a master’s in social work with a concentration in school social work from UW-Madison. She serves as a faculty liaison for the Upper School REDgen student chapter, teaches a psychology elective to juniors and seniors, and plays soccer weekly on an “over-40” women’s team in Milwaukee.



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