Building Connections Across the Generations
With insights from Open Friday Coffee special guest Roland Thompson, co-author of Grand Connect
When someone we love is making choices we don’t understand, our first instinct is often to explain more, advise harder, or find some way to help them change.
But stronger connection usually begins somewhere else.
You cannot control another person’s choices, but you can change how you show up in the relationship. Listen before advising. Ask questions instead of immediately providing answers. Become curious about the other person’s world rather than insisting they enter yours. When we stop spending so much energy trying to change someone else, we create more room for trust, connection, and genuine influence.
That was one of the ideas at the heart of a recent Open Friday Coffee conversation with my special guest, Roland Thompson.
Meet Roland Thompson
Roland and I met several years ago through Gary Barnes’ Business Breakthrough Bootcamp, and he is one of those delightfully multidimensional people where one conversation never quite covers everything.
For this Open Friday Coffee, however, I wanted to focus on one particular piece of his work.
Roland is the co-author, with Lee Ostler, of Grand Connect: Bridging the Gap Between Generations. He and his wife have a wonderfully large blended family, and Roland’s experiences as a parent, grandparent, adoptive parent and now great-grandparent helped draw him into a much deeper question:
How do we remain meaningfully connected with younger generations whose world may look almost nothing like the one in which we grew up?
That question matters far beyond grandparents.
It matters whenever we love someone whose choices, communication style, priorities or worldview differ from our own.
Connection Begins Where Control Ends
During our conversation, Roland gave everyone an imaginary magic wand.
You could use it to change exactly one person in your life.
Who would you choose?
A child?
A parent?
A spouse?
A boss?
Someone you desperately love but cannot seem to reach?
Then came the more difficult question:
Can you actually make that person change?
Roland’s answer, born from his own family experience, was no.
What we can change is ourselves.
That distinction sounds simple. Living it is much harder.
There is tremendous freedom, however, in realizing that another human being’s choices are not yours to manage.
You can work on how you listen.
You can work on how quickly you judge.
You can work on the questions you ask.
You can work on whether your presence feels safe enough for another person to tell you the truth.
That is very different from trying to engineer someone else’s life.
“Fish With Them in Their Pond”
One of my favorite phrases Roland shared was:
“Fish with them in their pond.”
In other words, connection doesn’t always begin by teaching someone what you know.
Sometimes it begins by becoming genuinely interested in what matters to them.
Roland told us about learning to understand interests and choices that initially made very little sense from his own generational perspective.
Instead of immediately dismissing them, he began asking questions.
What do you enjoy about this?
What do you want?
What interests you?
What could this become?
That shift—from instruction to curiosity—changes the conversation.
We don’t have to pretend every choice is wise.
We don’t have to abandon our own experience.
We simply stop requiring someone else to enter our world before we’re willing to meet them.
Ask Questions Before Giving Advice
This was another theme Roland returned to repeatedly:
Less advice. More questions.
Those of us who have lived a few decades have accumulated experience.
That experience can be valuable.
It can also become a wall if every conversation begins with:
“You should…”
“What you need to do is…”
“When I was your age…”
Sometimes the person sitting across from us doesn’t need another answer.
They need someone willing to listen long enough to understand the actual question.
Roland made a lovely observation during our conversation: the word listen contains the same letters as silent.
There is a lesson hiding there.
Listening requires leaving some empty space.
Trust Cannot Be Forced
Our original Open Friday Coffee theme that morning was learning to trust yourself, and Roland connected that beautifully to relationships.
We often want other people to trust us.
We want them to listen to us.
We want them to believe that we love them.
But trust is difficult to demand from another person.
It is something we cultivate through the way we consistently show up.
Are we listening?
Are we curious?
Can we allow another human being to make choices?
Can we be present without immediately trying to fix them?
Can we examine our own behavior before pointing toward theirs?
Those questions require self-trust too.
What Is Actually Yours to Change?
This is where Roland’s conversation intersected deeply with work I have been doing around Revenue Without Rush.
I spend a lot of time talking about where we place our attention, energy and effort.
And one of the quickest ways to exhaust ourselves is to labor over something that was never ours to control in the first place.
Sometimes that’s another person’s behavior.
Sometimes it’s an old identity.
Sometimes it’s a business process we’ve outgrown.
Sometimes it’s a belief about what our life is “supposed” to look like.
At the end of Open Friday Coffee that morning, I asked everyone a question that I think applies here too:
Where are you laboring too hard?
What are you pouring time, effort and energy into that may simply need to be released?
What identity, habit, behavior or thought pattern is requiring enormous effort to maintain?
And what might become possible if you stopped?
Revenue Without Rush isn’t an argument against effort. It is about stewarding where that effort goes.
There are things worth working for.
There are relationships worth tending.
There are creative ideas worth bringing into the world.
But sustainable work requires recognizing the difference between what we can influence and what we are trying unsuccessfully to control.
A Question to Take With You
Think of one relationship in your life where you wish something were different.
Then, instead of asking:
“How do I get them to change?”
try asking:
“What can I change about the way I show up?”
Perhaps the next step isn’t another conversation.
Perhaps it’s a better question.
Perhaps it’s listening.
Perhaps it’s learning something about their world.
Perhaps it’s giving the relationship some space.
Connection doesn’t require control.
Sometimes it begins when we finally put the magic wand down.
Learn More About Roland Thompson
Roland Thompson is the co-author, with Lee Ostler, of Grand Connect: Bridging the Gap Between Generations, a resource created to help grandparents build stronger, more intentional relationships across generations.
The Grand Connect project also includes resources designed to help grandparents stay connected with the people and moments that matter in their families.
Learn More about Grand Connect
Come Sit on the Porch
Conversations like this are why I created Open Friday Coffee.
Every Friday from 7:00–7:45 AM Mountain Time, we gather for a free, open conversation around rebuilding, creating, learning, and navigating the seasons of life and business.
Some Fridays I teach.
Some Fridays the people in the room bring the lesson.
And increasingly, I’m inviting special guests like Roland to sit on the porch with us and share what they’ve learned along the way.
Restore. Renew. Reform.
Everyone is welcome.