I have many teens come into my office throughout the school year and the best advice I have ever received from a high school college counselor is: Don’t ask about college. It is natural to want to ask teens and high school seniors, “where do you want to go to college?” or “what schools are you looking at?” but I have found that these questions build a barrier to having authentic conversations instead of trust. Teens are under so much pressure to appeal to, apply to, and attend the “right” college. We need to give them a break from thinking about their future. Here are some questions or conversation starters that focus on who teens are now.
What’s on your mind? I first learned about asking this question in a leadership book for managers. It lets the person you are talking to set the agenda, and I figured, why not also use it with teens. They can choose to be as deep or as surface as they like, but I like it because it sends the message that you care about what they are thinking about or going through.
What did you do for yourself today? We are constantly asking our teenagers to give their attention outside of themselves. I like this question because it sends them the message that they are worth investing in. We have seen how important self care is during the pandemic and this applies to teens as well. It is never too early to start a self care practice, and having one in place before adulthood will give our teens a boost going into the real world.
Who are you connecting to? This question is so much better than the age old and presumptuous question of “do you have a boyfriend/girlfriend?” It allows the teen to open up about a friend they may be enjoying spending time with, a popular musician that just put out a new album, or an adult role model they are enjoying learning from. Like some of the other questions, the teen can choose how much or little they want to open up and not feel cornered with expectations.

What is the last thing you did for play? Let teenagers be kids! Encourage play time or downtime that is playful. I am biased toward play that doesn’t involve screens, and play can be organized like a sports team or spontaneous like gathering some friends and family for board games. My family recently played Left, Right, Center at a family gathering and we had a real laugh-out-loud time together.
What is bringing you joy? I think we could all use a little more joy right now, so let’s cultivate it in teenager’s lives. Joys can be small or big and we may be surprised by the answer a teen gives. I ask students this question when they are in my office and usually I hear answers like “shopping” or “hanging out with my friends,” but I had one student say “watching my little sister play basketball brings me joy.” Her answer was heartwarming and genuine and I felt like I got a glimpse of her soul I had never seen before. Her joy brought me joy in one simple answer.
While college should be a topic of conversation, it should not be the only topic of conversation. I have made it an unwritten rule that my office is a college free zone, unless a senior walks in wearing a new college sweatshirt and I ask “ does that sweatshirt have any special meaning?” It only takes one big smile or a shake of the head to know the answer.
I can’t guarantee that teens will not give you some side-eye after asking these questions, but at least it is a starting point for communication. Try some of these while in the car together or at the dinner table. They can choose how broad or deep they want to go with the answers and my suggestion is to meet them where they are. Listen. Really listen and don’t pry. Follow up questions are good but be organic. No one likes an agenda, especially teens, but we all like to feel connection.