In this episode of The Cool Grandpa Podcast, I return after a short break to share powerful tools grandparents can use to connect deeply with their grandchildren.
I talk openly about my own journey over the past year — from navigating career changes and health challenges to stepping into a new role as a special education teacher. With those experiences, I’d like to introduce a practical worksheet designed to spark meaningful conversations with grandchildren.
The episode explores three simple but profound questions:
- How would people describe you if you left the room?
- How do you WANT people to describe you?
- What do you want to be doing in five years?
I explain how grandparents can guide kids (and even adult children) through these prompts in age-appropriate ways, helping them discover their identity, build confidence, and set meaningful goals. I also believe that these simple yet powerful questions can help intentional grandparents and parents become an “accountability coach” without being intrusive — keeping our cherished conversations supportive, fun, and impactful.
Whether you see your grandchildren every week or connect mostly by phone or video, this episode provides a simple framework to nurture strong relationships and help your grandkids envision their future.
Resources Mentioned:
- Ted Page’s The Good Grandpa: Stories from the Heart of Grandfatherhood
- You can find our conversation with Ted using this link: https://cool-grandpa.us/2025/06/05/good-grandpa-ted-pages-journey-from-blog-to-book-ep-233/
You can also watch this episode on YouTube by using this link: https://youtu.be/WWY_SCVmrjc
More Than Grand 
Grandfathers have a unique and meaningful role to play in grandchildren’s development, yet they often find themselves behind the scenes, on the sidelines, or less engaged than they’d like to be. This masterclass delivers a playbook for helping grandfathers level up their influence and impact. Listeners to The Cool Grandpa Podcast can receive 40% off this course by using Cool40 at checkout.
Founded in 2011 by Aaron Larsen as a way to honor his grandparents, GrandparentsAcademy.com is the world’s first and only online academy dedicated to helping grandparents grow meaningful relationships and rich legacies with their loved ones.
