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:

1. How would people describe you if you left the room?
2. How do you WANT people to describe you?
3. 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.com/2025/06/05/good-grandpa-ted-pages-journey-from-blog-to-book-ep-233/

Worksheet download

You can also watch this episode on YouTube by using this link: https://youtu.be/WWY_SCVmrjc