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INSIGHTS
Why Families That Endure Decide Early
Shannon Gill · October 25, 2026
Most of the principals I sit with are very good at decisions. They’ve made thousands of them, many under pressure, when the stakes were high and real money was on the line. They know how to read a deal, a market, a partner. Decisions need to be made, and they make them.
But some decisions get left to “we’ll get to it eventually.”
Those decisions are of a different kind. Not because they’re complicated. The accountants and lawyers are there to handle that, and they handle it well.
They’re personal. “We’ll get to it later.” “There’s time for that.” “That’s not pressing right now, steering the boat is.”
The business is doing well. Until it’s not. The founder is healthy. Until they’re not. The children get along. Until they don’t. You’ll eventually get to it. Until you can’t.
When a family delays a business decision, the cost is usually immediate and visible. An opportunity lost. A deal lost. A competitor that moved first. When a family delays a continuity decision, the cost doesn’t show. It ripples and compounds quietly. Every year the decision waits, a few options expire with it, and the conversation changes.
Is the founder still there to make the call? Are the relationships what they used to be, between partners, siblings, parents and children? Is the market where it needs to be if something has to be sold? By the time the decision has to be made, the time to make it well has passed. It gets made with fewer options and more people in the room than anyone would have chosen.
Deciding early is not deciding fast. Leadership takes years to transfer, as it should. Early means something narrower: settling what will matter most before it is needed, while the options are still in your favour.
What runs against intuition is who waits. The families that have built the most, across generations, are often the ones that wait the longest.
Part of it is confidence. Someone who has faced every obstacle along the way, and solved it, reasonably believes this will be handled too when the time comes. Part of it is control: the thought of losing it, or of having to step back. And then there is the thought itself: not being there. A reality every one of us faces eventually. Very few people are willing to sit with it, and fewer still with their family, partners and advisors around the table.
When I’m sitting with a family and their professional counsel, the numbers are the easier part. The tax matters, and rightfully so. But the question I always come back to is a different one: when the transition happens, what has to be true for you to call it done well? Most often, the answer I hear back is family harmony. Rarely is it the tax.
Families that endure aren’t more cautious. They treat the personal questions as decisions, not as conversations for later.
What does continuity mean to us? Who owns what? Who decides? Who gets paid out, and from where? By the second generation, those questions no longer belong to one person. They belong to the whole family. The families that endure settle the answers while those answers are still theirs to settle. So when that day comes, and it comes for everyone, the decisions are already made. The family is left to grieve, heal and celebrate a life rather than negotiate.
Every family will make these decisions eventually. The only real question is when, and by whom. The families that endure make them early, on their own terms, while everyone is still at the table.
Shannon Gill is Founder & Principal of Gilko Capital, which advises Canada’s enterprise families and their advisors on life insurance.GILKO CAPITAL
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