By Jacoline Loewen

I’ve spent decades working with business owners, watching them wrestle with the messy, emotional, and downright human side of selling their companies. It’s never just about the money—it’s about legacy, family, and the promises you made over dinner tables and late-night boardroom talks. This post, I’m tackling a topic that keeps many of you up at night: how do you sell your business to a third party when you’ve sworn it would stay in the family? And while we’re at it, let’s talk about compensation fights between your kids, the advisors who’ve left you with a tax bomb, and why your business might not be the legacy you think it is. Buckle up—this is going to feel like a therapy session with a side of spreadsheets.

# 1. Selling to a Third Party After Promising the Kids the Keys

You’ve spent years telling your children the business would be theirs. Maybe you even pictured them running it, passing it down to their own kids. But now, the market’s hot, a buyer’s knocking, or you’re just tired—and selling to an unrelated third party looks like the best move. How do you navigate this without torching family dinners for the next decade?

First, own the pivot. You’re not betraying anyone—you’re making a tough call for the right reasons. Maybe the kids aren’t ready to run it (or don’t want to). Maybe the business needs more capital or expertise than the family can provide. Whatever the reason, be honest. Sit the family down and explain why selling makes sense—not just for you, but for them. Paint the picture: liquidity now could fund their dreams, secure their futures, or give them freedom to pursue their own paths.

Next, get creative with the transition. If the kids are emotionally tied to the business, explore ways to keep them involved post-sale. Could they stay on as advisors or minority shareholders? Could the sale proceeds fund a new family venture they actually care about? The goal is to shift the narrative from “I’m selling your inheritance” to “I’m unlocking our family’s next chapter.”

Finally, bring in a neutral third party—a mediator or family business consultant—to facilitate the conversation. They’ll help you avoid the trap of playing favorites or letting old grudges derail the process. Selling doesn’t mean breaking your promise; it means redefining it. Done right, your kids will thank you for the clarity (and the cash).

# 2. Navigating Compensation Wars Between a Star Kid and a Slacker

Let’s talk about the elephant in the room: one of your kids is a rockstar, driving the business forward, while the other… well, they show up when they feel like it and they hate capitalism. How do you pay them fairly without sparking a family feud?

Step one: separate ownership from employment. If both kids own equal shares of the business, that’s fine—dividends or profits can be split evenly. But compensation for work? That’s based on performance, not DNA. The high-performer should be paid market rates for their role, the same as any non-family employee. The non-performer? Pay them only for what they actually do. If they’re not contributing, they don’t get a paycheck just for being your kid.

Step two: get transparent. Hold a family meeting (yes, another one) and lay out clear job descriptions, KPIs, and salary benchmarks. Use data—Glassdoor, industry reports, whatever it takes—to show why the high-performer earns more. If the non-performer feels slighted, give them a path to step up: training, mentorship, or a specific role they can grow into. If they don’t take it, that’s on them.

Step three: protect the business. If the non-performer is dragging things down, consider an exit strategy for their role—maybe a buyout of their shares or a severance package tied to a graceful exit. Harsh? Maybe. But a family business isn’t a charity, and resentment between siblings can poison everything.

Pro tip: hire an independent HR consultant to review compensation and present findings. It takes the heat off you and signals fairness. The goal isn’t to pick a winner—it’s to keep the business (and your family) intact.

# 3. The Massive Tax Bill No One Warned You About

You’ve built a successful family business, and you’re ready to pass it on to your kids or sell it and retire. Then you die, and your kids are hit with a capital gains tax bill so big they have to sell the business just to pay it. No liquidity, no plan, just a mess. Who’s to blame? Your accountant, financial advisor, lawyer, or all of them?

The answer is D. All of the above.

Here’s why:

- Accountant: They should’ve flagged the tax implications of your estate plan years ago. Capital gains tax on a business transfer can be brutal, but tools like estate freezes, trusts, or insurance policies can minimize the hit. If they didn’t bring these up, they failed you.
- Financial Advisor: They’re supposed to model your wealth and ensure liquidity for taxes or succession. They should be able to discuss next-gen asset management too. If they didn’t stress-test your plan for a worst-case scenario (like your death), they are dropping the ball..
- Lawyer: They draft the wills, trusts, and shareholder agreements. If they didn’t structure your estate to avoid or defer taxes—or at least warn you about the risks—they’re not doing their job.

The real issue? Silos. Too often, these advisors don’t talk to each other. You need a quarterback—someone who coordinates the team to create a cohesive plan. If you don’t have one, hire a family office advisor or wealth planner/strategist to oversee the big picture.

And don’t just blame the advisors—take responsibility. Ask hard questions. Demand scenarios. If you’re not hearing about taxes, liquidity, or succession risks, fire someone. Your kids shouldn’t pay for your blind spots.

# 4. Your Business Isn’t Your Legacy—Your Family Is

I’ll wrap up with a question I’ve asked hundreds of audiences: *Who founded Canadian Tire?* Crickets. Always. No one knows (it was the Billes brothers, by the way). Yet Canadian Tire is one of the most iconic brands on Earth. If no one remembers its founder, do you think your family business will be your lasting legacy?

Spoiler: it won’t.

Your business is a tool, not a monument. It’s a means to create wealth, security, and opportunities for your family. But your real legacy? It’s your kids, your values, the way you shape their lives. A family business can tear families apart or bring them closer—it’s your choice.

So, as you think about selling, compensating your kids, or planning for taxes, remember this: your greatest work of art isn’t the company you built. It’s the family you nurture. Make decisions that strengthen those bonds, not break them.

Got questions about selling or succession? Drop me a line. I’m here to help you navigate the messy, human side of business.

Jacoline Loewen works with successful families to navigate their assets and family business. With her background, she’s seen it all—sibling rivalries, tax disasters, and everything in between. She helps business owners make smart, human-centered decisions to protect their wealth and their families.