Wealth and Relationships: Stop Playing Tennis in Family Conversations and Start Playing Catch

Wealth and Relationships: Stop Playing Tennis in Family Conversations and Start Playing Catch

A family council we worked with stopped meeting after a conflict about leadership style escalated into a family-wide disagreement.

The tension began with frustration about one person’s leadership approach. Their intentions were good — they were trying to move things forward — but their direct communication style came across as abrasive to others. Over time, conversations became defensive, then personal.

Instead of addressing the impact, family members began fighting to be right — proving their point and blaming one another for the hurt that followed.

Eventually, the council stopped meeting altogether.

It wasn’t governance that failed. It was trust.

Families often believe the future will be secured through planning, governance structures, or financial strategy. But most conflict around assets doesn’t start with money — it starts with people feeling unheard.

Families don’t design a future alone. They navigate a future together — based on what matters to each other, rather than simply what needs to be done.

In our work preparing families for generational wealth and business transition, we often see conversations turn into conversational “tennis” — quick responses, corrections, and defensiveness.

A more productive approach is conversational “catch.”

Let the words land.
Pause before responding.
Ask: “Help me understand — what really matters to you about this?”

Often, a complaint about the past is really a request for the future.

Trust in families operates on two levels:

Transactional trust — Can we get things done together?
Relational trust — Do you care about me? Am I seen and safe?

Governance structures don’t create unity. Trust does.

Preparing a family for assets begins with preparing them to listen to one another.

Where in your family conversations are you trying to be right instead of trying to understand?