Questions for the Grads in Your Life
Graduation is a milestone; mark it with a great conversation. These questions will help.
In two weeks, my oldest child, Sam, will graduate from high school and, after a summer spent scooping ice cream, head to college in the fall.
For the last year, one question has dominated every conversation Sam has had with my friends, our extended family, and the neighbors: Where are you going to college?
Making the decision of what to do after graduation, whether from high school or college, is momentous of course. It deserves to be asked and discussed. BUT … it also jumps over so much about who Sam is right now, and what the experience of the last four years has meant to them.
Also, the “what’s next?” question is a little predictable—and by now you probably know that predictable, scripted questions are definitely not my thing.
So, inspired by a post from Jenny Rosenstrach, the author of Dinner: A Love Story, and a fellow mom of a 2025 graduate, I’m sharing a few out-of-the-box questions you can ask the grad in your life.
Here are the excellent questions Rosenstrach shared in her newsletter:
What would Freshman You be most surprised to know about Senior You?
What are you most proud of from the past four years?
Did you change your mind about anything while you were in college [or high school]?
In the future, when you picture your quintessential college day, what will you describe?
What are you looking forward to?!
And if you need a few more to get you through the long ride to the graduation ceremony, or the family dinner after, here are a few additional questions I wrote:
What advice would you offer to an incoming freshman?
What did you learn that you think you’ll still be using in 10 or 20 years?
When you’ve been away long enough to feel nostalgic for your experiences here, what memories will make you feel that way?
How do you think your classmates perceived you, and what do you want to change about that image as you move on?
What support do you wish you had in school? What support do you need now from me?
What are you glad to leave behind?
BONUS QUESTION
As a parent, there’s nothing so rewarding as seeing your kid make a wise and thoughtful decision for their future. (I’ll spare you the details, but just know I’m feeling proud.)
Think about the younger people in your life—maybe that’s your child or younger family member, maybe it’s a kid in your community, or a junior colleague.
What has a young adult done lately that impressed you? Tell them today.
I have clear memories of the adults (youth group leaders, college professors, employers) who built my confidence and helped me see my strengths. You have the opportunity to be that person for someone in your life today.
BONUS CONTENT
I'm offering a free, interactive workshop on May 30th to introduce the basics of Appreciative Inquiry — a strengths-based approach to growth, development, and transformation.
Whether you're leading a team, planning a change, coaching others, or just trying to figure out what's next for yourself — Appreciative Inquiry offers a powerful way to identify what works, imagine what’s possible, and move forward with purpose.
We'll cover:
✅ What Appreciative Inquiry is (and what it isn’t)
✅ How to think with an appreciative mindset
✅ Using the methodology to identify vision, lead change, and develop people
It's free, and everyone's welcome. Bring your curiosity — and maybe a colleague or two.
📅 Date: May 30
🕒 Time: 9 am, Central
📍 Register here