How To Tell Your Kids (And Employees) You're Selling

You’ve built something remarkable over 30 years, and now you’re thinking about an exit.

But there’s one conversation you’re dreading: telling your kids you’re selling their inheritance. And right behind that? Figuring out what to tell your employees without triggering mass panic.

Here’s what most business owners get wrong: they think selling means failing their family or abandoning their team. The truth is often the opposite. Selling—or partially selling—can be the best way to preserve your family’s wealth and secure your employees’ futures.

So today, I’m going to walk you through how to think about these critical conversations, who needs to know what and when, and why protecting wealth matters more than preserving legacy.

Selling doesn’t always mean selling—and your kids need to understand that first.

Before you have any conversation with your children, reframe what “selling” actually means.

Most owners think it’s binary: keep 100% or sell 100% and walk away. But sophisticated exits rarely work that way.

Often, a sale is partial—you might sell 60% to an investor while retaining 40%. Or you sell 100% but stay on for three years. Or you recapitalise, taking chips off the table while keeping upside exposure.

Here’s the critical insight: if 90% of your net worth is tied up in one illiquid asset, you’re taking an enormous risk with your family’s financial security. One industry disruption, one key customer loss, one regulatory change, and decades of wealth creation could evaporate (and let’s not even mention COVID 2.0!)

Selling or partially selling converts business equity into investable capital that can compound safely outside the business’s operational risk. That’s not abandoning your legacy—that’s smart wealth management.

The second generation makes a mess; the third generation creates a disaster.

There’s an old saying: the first generation builds it, the second generation manages it, and the third generation destroys it.

Here’s why this pattern matters for your exit decision.

The age gap between most business owners and their children is too large for a smooth transition. If you’re 60 and your kids are 30, they’re not ready to run what you’ve spent three decades building. They haven’t lived through the hard years, the near-bankruptcy moments, the customer crises that taught you everything.

And here’s what most owners don’t want to admit: their kids have watched them sacrifice evenings, weekends, holidays, and family time for the business. They’ve seen the stress, the sleepless nights, and the toll it’s taken on your health and relationships.

Most of them don’t want the same thing.

They might say they do—out of loyalty or guilt. But deep down, they’ve seen the price you paid, and they’re not interested in paying it themselves.

So when you think about “handing down the business,” ask yourself honestly: are you giving them an asset, or a burden?

A disengaged owner destroys more value than any external buyer.

Here’s the scenario nobody discusses at the braai: you keep the business in the family, but you’re mentally checked out.

You’re 62. You’ve been grinding for 35 years. You want to move to the coast, play golf, and travel. But you feel obligated to keep the business because “it’s the family legacy.”

So you stay involved—but half-heartedly. You’re not making bold moves. You’re not investing in growth. You’re managing, not leading. Meanwhile, your kids aren’t ready to take over, your senior team is frustrated, and the business slowly declines.

Here’s the uncomfortable truth: a good, well-capitalised investor who’s fully engaged will do more for your business—and your employees—than a disengaged family owner trying to preserve what exists.

Strategic buyers bring capital, systems, expertise, and growth resources that most family-owned businesses can’t access. They professionalise operations, expand into new markets, and create career opportunities that wouldn’t exist under family ownership.

Sometimes the best thing for the business is to bring in an owner who’s committed to its future growth, not just its historical legacy.

Don’t tell your employees—seriously, just don’t.

Now let’s talk about employee communication, because this is where most owners make costly mistakes.

The rule is simple: only tell your executive / senior leadership team when appropriate, but don’t tell other employees until the deal is nearly certain (and in many cases, only on conclusion).

Why? Because employees get distracted and confused. They start worrying about their jobs, updating their CVs, and mentally checking out long before any deal closes. Productivity drops. Key people leave. The value you’re trying to sell is eroding.

Your senior team needs to know because they’ll be part of due diligence, and buyers will want to meet them. But even with senior employees, timing matters—tell them too early and you risk leaks and unnecessary anxiety.

For everyone else? There’s nothing to discuss until there’s something concrete to announce.

And here’s the important framing when you do tell employees: a sale to the right buyer is good for them. It means capital for expansion, career development opportunities, job security backed by a well-funded owner, and better systems that make their jobs easier.

The narrative shouldn’t be “I’m abandoning you.” It should be “I’m setting this business up for its next chapter of growth, and that’s going to create opportunities for all of us.”

I am often called in to assist with communication with senior employees, minority shareholders, and even to prepare for the eventuality that an employee or customer might find out. The message I focus on is that we are looking for a strategic investor for growth, not looking to sell. The reality is that it would be quite reasonable later down the line for this to result in a sale, but it is wise not to call it that from the outset.

The conversation with your kids should be about wealth, not legacy.

When you finally sit down with your children, don’t lead with “I’m selling the business.”

Lead with “I’m making a decision to protect our family’s wealth.”

Explain the concentration risk: “90% of our net worth is in this one business. If something goes wrong, everything we’ve built is at risk.”

Explain the market opportunity: “We’ve had interest from buyers at valuations we may never see again. This is a chance to convert that value into investable capital while the market is strong.”

Explain the succession reality: “I’ve watched too many families destroy wealth trying to force a succession that wasn’t right for the business or the next generation. I don’t want that for us.”

And if they push back with “but this is our family legacy,” you can say this: “Our family legacy isn’t a business. It’s financial security, opportunities for your children, and the freedom to build your own path without the burden of managing something you didn’t choose.”

That’s not cold. That’s honest.

So if you’re wrestling with these conversations, remember this: selling isn’t failing. It’s strategic wealth management.

The families who preserve wealth for generations aren’t the ones who cling to legacy at the expense of financial security. They’re the ones who make hard decisions to protect what they’ve built—and give the next generation the freedom to build their own path.