“The most important thing in communication is hearing what isn’t said.”
~ Peter Drucker
There is a pattern I’ve come to recognize in many family enterprise conversations. The agenda is clear: succession, ownership, leadership, or compensation. Everyone arrives with clear intentions, ready to resolve a practical issue.
Then the conversation shifts. A discussion about dividends becomes one about fairness. A leadership decision becomes unexpectedly emotional. People respond not just to the issue but also to their experiences and relationships.
Over time, I’ve come to wonder whether these conversations are sometimes about more than they first appear. The issue is real, but it may not always be the conversation the family is actually trying to have. Recognizing that distinction can often lead to a more constructive path forward.
Not Where It Became Visible, But Where It Began
One of the privileges of my work is that families invite me into their most important conversations. Over time, I’ve noticed that while every family and every enterprise is different, certain patterns have a way of repeating themselves.
That observation has led me to a question I now carry into many of these conversations: Where did the process really begin? Not where it became visible, but where it first took shape.
A discussion about compensation may reflect something beyond just compensation. An ownership conversation may carry unspoken questions of belonging. A founder’s reluctance to step away can appear to be a governance issue while also touching identity, purpose, or the uncertainty of letting go. The issue on the agenda matters, but it isn’t always the whole story.
When the Decision Isn't the Whole Story
One pattern I’ve noticed over the years is that the issue a family is discussing isn’t always where the tension began. What first appears as a conversation about compensation, ownership, or succession can sometimes reflect experiences, assumptions, or relationships that have been building long before the meeting itself.
Perhaps that’s why some conversations can feel incomplete. A decision is reached, yet something remains unresolved. The agenda moves forward, but the underlying tension seems to find its way into the next conversation.
That observation has changed the way I think about this work. Helping families navigate difficult conversations certainly matters, but I’ve found it equally valuable to pause and ask whether the conversation on the agenda is the one that most needs attention. Simply approaching a conversation with courage may not always be enough if the more profound questions remain unexplored.
The Questions I've Learned to Ask
Over time, that perspective has changed the questions I bring into the room. Rather than beginning with, “How do we solve this problem?” I often find myself asking, “What else might be influencing this conversation?” What experiences have shaped the perspectives in the room? What assumptions have gone unspoken? How might each person be interpreting the same situation differently?
I don’t ask these questions because I expect immediate answers. I ask them because they create space for curiosity. In my experience, when people become more interested in understanding one another than defending their position, conversations often become more productive. The issue itself may not disappear, but the conversation around it often begins to change.
Concluding Thoughts
One paradox of family enterprise is that those who know one another best often find it hardest to see the patterns they’ve created together. That isn’t a failing; it’s simply the nature of living within a system. Which is why facilitation has never felt, to me, like leading a conversation. It feels more like holding up a mirror, creating space for families to see their dynamics with greater clarity.
Governance, succession planning, and clear agreements all play an important role. Their greatest value, however, may be in helping families better understand themselves. Alongside businesses and wealth, families also pass on stories, expectations, ways of communicating, and ways of belonging.
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
