How to Talk to Your Kids About Joining the Business
Start where every successful transition begins: with curiosity and a conversation.
There comes a moment in many family businesses when a question starts to emerge, quietly at first, then more clearly: Could this be something my kids are part of? Whether the thought is thrilling, daunting, or somewhere in between, it marks the start of a different kind of planning.
This isn’t just about exit strategy. It’s about legacy. Continuity. And perhaps most importantly, your future, your kids’ future, and by extension, your family’s future.
Before you talk about ownership, titles, or timelines, you need to talk about interest, curiosity, compatibility, whether there’s a future here, and whether you want to build it together.
This is where the real succession plan begins.
Let Curiosity Lead
If your kids are still young, too young to even think about their own careers, this isn’t about steering them toward the business. It’s about creating a relationship where curiosity, learning, and open dialogue are normal. Invite them to the office. Let them ask questions. Share stories about your day. These small moments lay the groundwork for future conversations.
Then, as they grow older and start forming their interests and aspirations, the real conversation begins. In many family businesses, that conversation has already started quietly, informally, and over years of osmosis. Business talk at the dinner table. Rides to and from the office. Being 'volun-told' to help with odd jobs, events, or summer roles. Sometimes they’re paid, sometimes they’re not. But almost always, they grow up familiar with the rhythm of the business long before any formal role is discussed.
Start by getting curious, not about what your kids think of the business, but who they are: What are they interested in? What makes them feel energized? What do they want for themselves?
You Know What They Say About Assumptions
One of the most common mistakes founders make is assuming their child wants what they wanted. The same ambition. The same responsibilities. The same finish line. But sometimes it isn’t about being an entrepreneur, it’s about the business you're in. My parents always said, "We chose the travel industry, you didn’t." That reminder helped me see the difference between a career path and a legacy expectation.
The best early conversations are never pitches. They’re explorations. Ask them questions that show you're open to all answers, including ones you may not want to hear.
"Have you ever thought about getting more involved in what we do?"
"What parts of it do you find interesting? What parts don’t appeal to you?"
"What are you excited about building for yourself over the next five or ten years—in or out of our family’s current business?"
Their answers might surprise you. And that’s the point.
Share Without Selling
You don’t need to lay out a 20-year transition roadmap or know your own timeline yet. But your child will benefit from understanding your current thoughts:
Why did you start the business?
What does it take to run it?
What are you proud of and what keeps you up at night?
Are you open to passing it on (and if so, what might that look like)?
When you share openly, it gives them permission to do the same. And it’s worth remembering, they’re already part of the story. They may not have chosen this path like you, but they were born into a version of ownership. You’re not handing over the keys. You’re helping them understand what it means to hold them.
Talk About Timing
If they are interested, make it clear there’s no rush. Some children enter the business at 25, others at 45. There’s no perfect moment, but there is a perfect mindset: one where both parties are ready to commit to the process. You might say something like:
"Just because we’re talking now doesn’t mean you need to decide. There’s no clock. But I do want to make sure we can talk about this openly, whenever you’re ready."
Setting a tone of patience and openness helps avoid the pressure that can make children feel like they’re being pulled into a future they didn’t choose. It also opens up room to talk about how (and whether) they could realistically step in. Is this a business where someone from outside the industry can find a path in? Are there roles, like General Manager or VP, that allow for leadership without deep technical experience? Or is this a business that demands hands-on learning or credentialed expertise before taking on responsibility? These are practical questions, and they deserve honest answers early on.
Be Honest About the Hard Stuff
If you’re going to invite your kids into the business, invite them into reality. That means talking about what the company earns, owes, and spends. If you’ve signed personal guarantees, they should know. If margins are thin and succession will require reinvestment, they should understand that too. You would never make a big decision, an investment, a hire, a deal, without first understanding the parameters, even if the decision remained uncertain. You owe your kids the same.
This isn’t about burdening them. It’s about respecting them. Sharing the whole picture shows them what’s really involved and gives them a chance to opt in with their eyes open. That includes giving them a tangible sense of what the business has provided over the years: the lifestyle, the opportunities, the family security. It helps them understand what’s at stake, not just what they’d be taking on, but what they’ve already benefited from.
Keep Talking
If you have multiple children, each brings a different personality, set of interests, and relationship to the business and you. Some may want to lead. Others may prefer to stay involved at a distance or not at all. That’s okay.
Leadership, employment, and ownership are three different things, and part of your role is to help define what makes sense for each. That might look like voting shares, board participation, or simply having a voice at the table without a formal title.
The key is to make space for individual conversations, not just family-wide discussions. When expectations are personalized and clearly communicated, resentment is less likely.
Succession isn’t a one-time talk. It’s a series of honest conversations, some small, some significant, that build clarity, trust, and a shared sense of direction.
Even if they don’t join the business, you’ll know you handled it with clarity, integrity, and love.
Thinking about what comes next?
We work with family businesses across Canada and the U.S. to design succession plans that work in the real world, not just on paper. Book a confidential call if you want to start the conversation or deepen one already in progress.