One of the most important goals I have for students is that they feel empowered to achieve their goals and create the academic experience they want to have. And one of the most important skills I help them develop to achieve that goal is self-reflection. 

By asking targeted reflection questions each time I speak with my students, I give them a safe and structured opportunity to assess and articulate their thoughts and feelings, and I get information that I need to best support them at that moment.

The exact questions I ask are all variations of a small set of short but powerful open-ended questions that my students come to expect from me over time. I ask some of these questions just once a year, some once a month, and some once a week.

The beauty of these questions is that parents can also use them to connect and reflect with their kids on a regular basis. And while you may be thinking, “This won’t work for me, my (pre)teen never responds to my questions with more than two words,” don’t fear. Terse responses are normal, especially when these kinds of conversations are new, and even short responses can be valuable.

The key is to build these conversations into your and your child’s routines so that over time your child gets practice thinking about and answering these questions. As they start to expect to be asked to reflect in these ways, they’ll be more prepared to answer your questions. Then, they’ll be able to give you more information about what they’re thinking and how they’re feeling.

Questions to ask weekly or daily

Start incorporating reflection questions into your conversations with your child during a time that you see them regularly — the ride home from school, the dinner table, as you say goodnight. If you don’t have much time, or their attention is short, just ask one question. Remember, each question is powerful in and of itself. These questions don’t demand a long conversation to have their intended impact.

Listen to your child’s response, and affirm that you’ve heard what they said. Don’t try to solve any problems you hear, and try not to judge anything they say as positive or negative. Just let them know that you’ve heard them.

Then, answer the question yourself. Even if it doesn’t seem like your child is listening, they notice everything that you do. Your own responses will provide a model of reflection skills that your child can build on while they’re learning these skills themselves. Furthermore, answering the questions yourself will help show kids who tend to interpret questions as interrogation that you are genuinely trying to connect. Just make sure that the answers you’re sharing as the parent respect the boundaries of your relationship with your child.

About once a day or once a week, you can ask

• What is one thing that happened today (or this week) that you are grateful for?
• What was the most interesting thing that happened today (or this week)?
• On a scale of 1–5, how well did your routine work for you today? Why did you choose that rating?

If you can incorporate this reflection time into their weekly planning routine, even better!

Questions to ask monthly

One month into asking daily or weekly reflection questions is the perfect time to ask a few of the following questions. You may want to consider dedicating a bit more time to talk about these questions. Also, know that you are a little more likely to have to respond to your own question first to help your child get past an initial “I don’t know” response.

If your child has trouble answering these questions, try not to get frustrated, and don’t give up. Remember, part of the purpose of asking these questions is to help your child build reflection skills, and the only way skills are built is over time.

So even if things don’t go exactly how you want them to the first or second time you start these conversations, view it as an experiment. Try again next month at a different time and maybe with a different question.

About once a month, you can ask:

• What was the most memorable part of the past month?
• What was the biggest lesson you learned over the last month?
• How are you different than you were a month ago?
• On a scale of 1–5, how happy are you with how you spent your time? Why did you choose that rating?
• What is one thing you want to improve on this upcoming month? What actions can you take to work toward those improvements?

Questions to ask yearly

When I first start working with a new student, I reserve about 10 minutes to ask the questions below and record the student’s answers. This conversation gives me deep and immediate insight into the students’ current state of mind, the challenges they’re working through, and the things they want for themselves. Writing down the student’s responses lets me revisit this information throughout my time working with them.

Once a year, you can ask:

• What do you want for yourself in the next month? Next three months? Next year?
• Which of those things would have the most positive impact on your life?
• What do you need to accomplish each of those things? How can I help?

As with the daily/weekly and monthly questions, I highly recommend sharing your own responses with your child. Just make sure that what you share is appropriate and respects the boundaries of your relationship. You can each record the other’s answers and post them somewhere in the house where you will see them often. That way you can incorporate them into the reflection conversations that you engage in throughout the year.

Self-reflection is a skill to be learned. Like anything else, learning this skill takes commitment, consistent practice, and good models to emulate. And like anything else, it can be intimidating in the beginning. It is okay to make mistakes — for both you and your child.

If you have questions about your specific situation or would like support, please get in touch!

Best of luck, and let us know how your conversations go!

Laura Fragomeni is a Harvard-educated master academic coach and the founder of School Without Suffering, an academic coaching practice specializing in helping struggling students around the world be happy and successful.