How to Build a Strong Connection With Your Grandchildren

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by Jerry Witkovsky

A number of years ago I was talking with my granddaughter Katie, then thirteen, at the end of her school day. “So how was school?” I asked her. This time, Katie refused to give me an answer. She threw her backpack on the ground and folded her arms. “Grandpa,” she said sharply, “I’m more than just a student, you know!” Of course I knew! But did I, really?

Standard queries, preachy advice, the obligatory check-in-the-mail for birthdays and holidays – these weren’t the tickets for admission to Katie’s world, or to any other youngster’s world, for that matter. She had a rich, deepening life of the mind, full of dreams and convictions, doubts and fears. Now she was inviting me in to share it, through a small window that might soon close. It was that moment I decided I needed to research the positive power of the grandparent-grandchild connection. Here are some of the tips I have learned.


  1. Understand Boundaries

We, the grandparents, are not the parents.

Whenever I want to introduce a new idea with my grandchildren, I always talk to my adult children first. Parents are the conduit to this grandest love. For some grandparents, that may mean it’s time to put away judgment and to get rid of old scripts. Understanding boundaries are important. Talk to your adult children. They may not always agree with you, but starting with your adult children automatically brings you closer to them, giving you a chance to share how you feel, and to understand where they are coming from.

  1. Get Involved

I often wonder about my grandchildren’s world. Their passions and dreams, friendships and relationships with their family? How do they feel as they are growing up?

Schools are a great place to get started. Most of the schools offer programs for grandparents to get involved as well as access information on the school’s website to find out what they are learning about.

It’s about being proactive rather than reactive. School and friends are at the heart of an adolescent’s childhood. And, when asked, they love to show off what they are doing to their grandparents.

  1. Use the Power of Storytelling

What I learned that day with Katie was to never again ask, “How was school?” Many grandparents and parents can relate to the “grunt” that often serves as an answer to that question. Instead, I ask them to “tell me a story about school.” That small difference in framing makes a big difference in response.

An old adage says that a story is the shortest distance between two people. That is so true when a grandchild and grandparent connect. Stories expand the view into a grandchild’s world and vice versa. They also help grandchildren see that grandparents have a life of their own. They, too, had first days of school, broken hearts, found love, and more.

  1. Offer Valuable Lessons

Grandparents often ask me how they can pass values, not just valuables, onto the next generation.

A grandparent that values health and exercise can take their grandchildren on regular walks in their local botanical garden. Social justice issues can be embraced by volunteering together. They can take turns picking the cause. A grandparent who values inclusion and diversity might go with grandchildren to ethnic festivals and restaurants and infuse the experience with learning about the country and culture.

I have one initiative in particular, that I have introduced with my family to ignite conversations about values:

“The Four Jars,” whereby I give four mason jars; Helping, Spending, Saving and Investment, to each of my grandchildren on their 13th birthday. I follow up by giving them twenty one-dollar bills each month for the ensuing year, allowing them to decide how they would divvy up the money.  The Four Jars provides a platform and application for children to make values-based decisions, namely learning kindness, fiscal responsibility and saving.

  1. Make the Best Use of Technology

Just as a grandparent today may live their entire life without ever owning a smart phone, kids today will never understand a world without them. Technology plays a large part in our generational divide. We continue to compromise around technology and communication.

I like phone calls. I need to hear my grandchildren’s voices—electronic communication can’t replace that. They, on the other hand, are often busy and respond more quickly to a text. I have one friend who texts her grandchild every morning “I love you.” Her grandchild texts back “I love you, too.” And they make time on the weekend to talk, for full conversations. Together, we try to find the parts of each other’s world that overlaps.

Everybody Wins

When grandparents and grandchildren connect more deeply, it brings the whole family closer together across the generations.


About the Author

Jerry Witkovsky is an author and grandparenting activist. Since retiring in 1997 as General Manager of the Jewish Community Centers of Chicago, Jerry has focused his considerable energies on grandparenting – helping multigenerational families work (and play) together to create a rich family life. His joyful commitment to his six grandchildren (ages 14-34) and to their parents, and his passionate belief in the transformative power of becoming a “Teaching-and-Learning” family, is at the heart of his book, The Grandest Love: Inspiring the Grandparent-Grandchild Connection, and a curriculum for schools, the Grandparent-Grandchild Connection School Program. Learn more at or email Jerry at [email protected].

 All of this has been turned into a full curriculum, the “Grandparent-Grandchild Connection School Program,” being piloted at a private day school this fall.


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