Back to school: Five conversations to have with your teen right now
Summer’s end is a great time to reflect and set intentions for the year ahead. Lean into this liminal moment, when kids’ routines haven’t kickstarted but the school-year brain is gearing up, to have some non-judgmental, curiosity-driven conversations with your kids.
Most of us find it challenging to set, much less stick to, intentions. But the truth is: it’s hard to reach a north star you haven’t set. So it’s worth prompting some thinking about:
The habits your teen wants to hold onto (Friday night movie night) and the ones they want to get rid of (doomscrolling for an hour or five before doing homework)
Any goals they might have – big or small – and how they might reach those (make the volleyball team; improve at math, join a photography club)
The things that get in their way, and ways to get around those obstacles
Dates that feel like a clean slate—like New Year’s Day, or the first day of school—can significantly boost people’s motivation to pursue their goals. These landmarks trigger a psychological separation from the past, helping people feel distanced from past failures and ready to start fresh.
Here are five ideas for conversations to have in the next weeks. Of course, don’t bring them up like a drill sergeant and expect answers. Figure out ways to have them organically, being curious about your teens’ lives and open to helping them set some good habits. And note that these aren’t about grade, college or career targets. The goal here is to think about habits of practice more than performance.
Managing AI
Most kids are using AI. And most kids are not talking to their parents about it because they are worried they will be judged.* There’s no time like the present to ask some open-ended questions about the tools available, some of which are brand new to the market.
Which AI model do you like and why?
What do you use it for?
What is it helpful for?
Where has it disappointed?
Where have you been impressed?
This summer a lot of the major AI companies launched their own study bots (here’s a pretty positive take on ChatGPT’s Study Mode and Google’s Guided Learning). They are better than general AI at asking questions and not just providing answers, but they still seem to help too much, they are too agreeable (sycophantic) and a bit too eager to offer the answer. The release of these products could prompt questions like:
Have you tested the study tools?
How are they different from other AIs you’ve used?
Where are they helpful?
How do you make sure you are learning the stuff you need to and not just using AI to get an answer?
How do you make sure the bot doesn’t make you dumber?
Most humans want to take shortcuts, but if we do this with learning, we will be woefully at the mercy of tech companies that don't care if you are unemployable and lack critical thinking skills.
Getting enough sleep
When teens sleep enough their attention is better, they learn better and they have fewer friendship issues. The problem is, due to changes in circadian rhythms in adolescence, teens often don’t get tired and so go to bed too late. In my house, bedtime is ground zero for battles and it’s annoying for all of us (me because I am old and desperate to go to sleep, my eldest teen because she is young and buzzing with energy after 9 pm).
Try to talk about bedtime, even though your kids who may be closer to being adults than kids. You’ll find it’s way easier to have this conversation when it’s not 11pm with a test the next day.
How much sleep do you want to get?
What's the biggest obstacle to getting it?
How do you feel when you are rested vs being tired?
What do you think the optimal amount of sleep is to keep you happy, healthy and performing well?
What goes well when you are rested vs tired?
What can you do to get more sleep?
What can I say to you at 10 pm that will not elicit an eyeroll but may get you to go to bed (humor here helps).
Don’t be afraid to try hard
Learning is hard. The start of term, when there aren’t ten tests to contend with, is a good time to talk about that (encouraging your kid to lean into hard things when a major test is looming is like asking a chef to learn a new recipe during the dinner rush).
Have an honest conversation about struggle.
Encourage your child to reflect on the prior year and something they improved at. Do they remember being a novice? Do they remember gaining mastery?
What was hard last year? Why?
What worked in making it less hard? What didn’t?
What was hard at the start of the year that got easier (noticing improvement is helpful when the year starts and things feel overwhelming)
Remind them that often, when we are struggling with something, it is not a signal we are failing—its’s a signal we’re learning. Turning toward that struggle and not avoiding it is brave, and often effective.
There are always strategies to deploy when one gets stuck: Asking for help from a teacher, from a parent, a peer or AI are good ones. Study groups might be another. Five minutes of recap before the start of the school day might work for some.
A big reason kids fall behind is what Sal Khan, founder of Kanmigo calls ‘Swiss cheese holes’ in learning – gaps that start small and remain if they don’t get noticed. Teach your kid to notice their gaps and get the help they needs to fill them.
Find ways into Explorer Mode
Too often we focus on the negatives in our kids’ lives: the class that isn’t going well, the hated teacher, or terrible coach. With the breathing room of the final days of summer, focus on their strengths and interests and brainstorm ways to lean into those as the year goes on. In the book we call this Explorer mode: the place where curiosity meets drive. When kids are in Explorer mode they perform better, feel better and often, are nicer to others. Try asking:
What activities are you pumped up about? Where do you find yourself in flow, so absorbed that you lose track of time? How can we find more ways for you to do more of that?
How can I help you dig into the things you love vs things you need to do?
If they don’t have any big interests yet, don’t panic! Ask what worked in school, and what didn’t. When the year kicks off, ask about their favorite class – not their hardest one. And always make way for the worries. Before the year starts, ask:
Is there anything you are concerned about? Why?
How can I be useful to you when you are feeling overwhelmed?
It’s can be harder to get into Explorer mode when other things aren’t going well.
Set a family tradition
I have a friend in Minnesota whose family read a poem every night at dinner. There were three kids, so everyone only had to pick every five days. Did the kids love it? No. Did they do it? Yes. Had they read/heard hundreds more poems by the time they left the house due to the tradition? They had. (It didn’t happen every single day, but it happened a lot because they prioritized it).
This will not be every family’s tradition. Find yours. Maybe it’s sharing a song at dinner on Tuesdays, with a line on why you like it. Pick a headline from the news that gave you hope. Something that made you laugh (Tik Toks can be included!)
A few of ours:
Sunday night roast chicken (definitely the four of us, sometimes joined by cousins or a grandmother)
Daily Wordle battle
One nice thing – everyone has to say one nice thing about someone else. It has to be specific, not sarcastic and not the same thing you said before. We do this when we find ourselves bickering (anyone who has spent one second in our house knows this is a lot)
Sad-Mad-Glad – Remember this from the toddler days? Talk about something that made you sad, something that made you angry, and something that made you happy that day. It still has so much resonance!
Something kind you did for someone this week – less “all about me” more all about us.”
Just as it’s hard to have a productive conversation at work when a deadline is looming and everyone is stressed and fraying, it’s sometimes tricky to reflect on learning in the midst of it. So seize your moment now, expect some resistance, and persevere.
*According to data collected for the Understanding America Study, a longitudinal research initiative out of the University of Southern California, 22-26% of parents of kids in secondary school believe their children use GenAI for education-related purposes. Estimates on how much kids actually use it range from about half to just under three quarters, with one study from Cornell University showing that 70% of students in secondary school—middle and high school—regularly use AI. Qualitative research done by The Rithm Project, a nonprofit which works to help young people build human connection in an age of AI, revealed kids saying they use AI a lot but are wary to talk to adults about it for fear of being judged.



