How to ask your teen better questions about how they're doing
Specific, open-ended, fun, and a sense of gratitude
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Are you tired of one word answers when you ask your teen about their day? Chances are you're asking the typical "How are you doing?" or "How was school" type of question that just don't work to get teens to open up.
This week, we're exploring how to ask better questions that help you deepen your relationship with your teen.
📌 Anatomy of a good question
Open, but specific - Open ended questions are rooted in curiosity instead of soliciting information. Open ended questions often begin with “How?” “In what way?” “What?” and can’t be answered in one word answers. It’s important to make sure your questions are specific enough to bring to mind a clear answer for them. Questions like “How was your day” are too broad and when your teen can’t immediately think of how to answer, they’ll default to their one word answers.
What, not Why - Questions that use “Why” often come off as judgmental if the tone is “off”. A simple trick is to switch out “Why” with “What”. For example, “What made you feel like that was the best solution?” instead of “Why did you do that?”.
Surprising and thoughtful - When you repeat the same questions often, it’s easy for your teen to tune out. But if you ask a surprising question or a question that’s thoughtfully tailored to the context, they’re more likely to pause and think about it because it also intrigues them. So, mix it up!
Right place, right tone - Even more important than the content, is your tone and the setting. Teens can sniff ulterior motives from a mile away, so you’ll want to make sure you’re genuinely curious to listen when you ask questions meant to build connection. Further, inviting your teen to a conversation instead of interrupting them while they are relaxing (e.g, play games, watching TV) can help them feel in control and respected – both are grounds for better conversations! Finally, as therapist Dr. Stemen shares, “After having worked with teenagers for many, many years, I can say that the single best way for parents to get their teens to open up to them isn’t through saying anything specific, but rather through engaging in activities with them. This allows conversation to flow naturally.”
🧪 5 conversation starters to try
"What’s something that was unexpected/surprised/challenged you today?"
Focusing on a specific emotion makes it easier for your teen to think about what to share. This question can also be followed up with "What was that like for you?" or "What didn’t you like about that?" to go further.
"You're the DJ, play what you want to listen to!"
Music can reveal a lot about how someone is feeling, the type of story, or mood they're connecting to at the moment. Plus, it gives your teen a chance to feel in control. So let them put on a song of their choice on the drive back from school and ask about the artist, what they enjoy about the song, or where they first heard it.
"What’s something you’re learning right now that you’d like to know more about?"
This doesn’t have to be limited to what they’re learning in school. This question can help them see that they’re constantly learning about the world (e.g, via news, reflections, observations, school), and prompt them to go deeper with further self-guided research. It also opens up an opportunity to build intellectual intimacy.
"If your day was an emoticon, what would it be?"
Try this one in the family group text as a way of sharing a quick summary of each family member's day. With hundreds of emoticons to choose from, this check-in routine can be fun and elicit different responses each day. Some fun ones could be: 😅 🥰 🤡 🔥 🧡 💩 Alternatively, at the dinner table, you can try going around and giving a one word summary of your day.
"What is one way someone helped you today?/How did you help someone today?"
Gratitude is the antidote to negative emotions like anger, worry, and hurt. As a teen, it is easy to focus on what’s wrong and the daily frustrations of life. When you ask them to pause and practice gratitude regularly, it can help rewire their brain to think more positively.
Cherish’s Question of the Week
For the dinner table, car ride, or whenever you get to sit down with your teen.
What is something you wish you got to talk about more often or that people would ask you about?
Cherish's Reflection of the Week
A moment for yourself to slow down, reflect, and Cherish.
What’s one way I can soothe my feelings of rejection when my teen shoots down my attempt to ask questions about their day?
❤️ More things we Cherish
If you have 1 minute - Read through a quick refresher on how to practice active listening.
If you have 5 minutes - Enjoying conversation starters to try with your teen? Then you might want to try out The [And] Family Edition card game. It’s jam packed with questions that challenge you to be a little more vulnerable than usual.
Deeper dive - Check out this experiment about how much gratitude can change your level of happiness.
What do you Cherish? Share a tip, story, or question you may have around parenting teens with us by replying to this email!
About Cherish
Cherish combines research and empathetic support in the form of 1:1 parent coaching, curated parent circles, and personalized content to help parents develop the skills, awareness, and community needed to parent confidently. We know being a parent can be tough - and it’s even tougher as your kids hit their teenage years. That’s why we created Cherish to support you each step of the way!
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