One of the more fascinating aspects of family life is how easily familiar roles reappear. We leave home, build careers, raise families, and take on significant responsibilities. Experience changes us in countless ways.
Then we return home for a holiday, a family gathering, or a weekend together, and within moments something feels familiar. Conversations unfold in ways we’ve experienced before. We respond to one another in ways that feel like they belong to an earlier chapter of our lives.
It isn’t that we’ve stopped growing. It’s that families have long memories. Over time, every family develops patterns that help it function, and those patterns often persist long after the people within them have changed.
For families who own businesses together, those same patterns can quietly influence conversations far beyond the family table.
The Patterns Families Carry Forward
Every family develops an unwritten way of relating to one another. Responsibility tends to settle with certain people. Others become the peacemakers, the challengers, or the quiet observers. These roles often emerge naturally and, at one time, may have served the family well.
The challenge is that while people continue to grow, the family’s expectations don’t constantly evolve at the same pace.
That becomes particularly relevant in family enterprises. Conversations about leadership, ownership, succession, or governance are shaped not only by today’s decisions but also by relationships that have developed over decades. Sometimes families are responding as much to familiar roles as they are to the issue itself.
Beyond Personality
Understanding personality can help families communicate more effectively, but it doesn’t explain everything.
I’ve often found it more helpful to ask a different question: Who does this relationship invite me to become?
A capable executive may find it difficult to express an opinion at the family table. A confident business owner may find themselves slipping into an old role without realizing it. Rather than seeing such behaviour as regression, it may simply reflect the influence of relationships that have remained familiar even as the people within them have changed.
Where It Matters Most
In family enterprises, these patterns often become visible during significant decisions. Succession planning, ownership transitions, governance discussions, and estate planning rarely involve technical questions alone. They also reflect years of family history and established ways of relating to one another.
In my experience, families rarely struggle because they lack capable advisors. More often, they have excellent legal, tax, and financial advice. What proves more challenging is recognizing the patterns shaping the conversation itself.
When families begin asking, “What’s happening between us?” alongside “What decision are we trying to make?” conversations often become more constructive, and decisions tend to follow with greater clarity.
Concluding Thoughts
“When we know better, we do better.” — Maya Angelou
Perhaps one of the greatest strengths a family can develop is the ability to see one another as they are today, rather than through roles formed years earlier.
Families evolve. Businesses evolve. The relationships that support both need the opportunity to evolve as well.
I’ve come to see holiday gatherings as a gentle reminder of that reality. They reveal patterns that are easy to overlook in everyday life but can have a meaningful influence on the conversations that shape a family’s future.
ABOUT THE AUTHOR
As the Senior Wealth Advisor at Beacon Family Office at CI Assante Wealth Management Ltd., Cory Gagnon has supported successful family enterprises to preserve, protect and transition their wealth since 2011.
Cory’s personal objective as a Wealth Advisor is simple. He is committed to supporting families to take control of the areas of their lives that truly matter to them. This commitment revolves around using specific tools and strategies that enable families to take action with confidence which will support them through life’s critical transitions.
ABOUT THE AUTHOR
As the Senior Wealth Advisor at Beacon Family Office at CI Assante Wealth Management Ltd., Cory Gagnon has supported successful family enterprises to preserve, protect and transition their wealth since 2011.
Cory’s personal objective as a Wealth Advisor is simple. He is committed to supporting families to take control of the areas of their lives that truly matter to them. This commitment revolves around using specific tools and strategies that enable families to take action with confidence which will support them through life’s critical transitions.
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Beacon Family Office at CI Assante Wealth Management Ltd.
Suite 519, 10333 Southport Road S.W.,
Calgary, AB T2W 3X6
